Irene Komnene Doukaina
Irene Komnene Doukaina or Eirene Komnene Doukaina was an Empress of Bulgaria during the Second Bulgarian Empire and Byzantine princess.
She was the third wife of tsar Ivan Asen II of Bulgaria.
She was the mother of tsar Michael Asen I of Bulgaria.
Ivan Asen IV of Bulgaria
Ivan Asen, also known as Ivan Asen IV was a Bulgarian Prince, third son of Emperor Ivan Alexander from his first wife Theodora of Wallachia.
He was born c. 1326.
Little is known about him.
In the eighteenth year of the reign of Ivan Alexander- i. e. 1349- he and his troops faced a 20,000- strong Ottoman army under the command of Murad I's elder brother Syuleiman.
The fierce battle between Bulgarians and Turks took place in the area around Sofia.
According to the Anonymous Bulgarian chronicle," the Turks killed Asen and a great number of Bulgarians"; according to Ottoman chronicles" many jannisaries perished" in the battle.
That shows that the battle claims many casualties from both sides and Ivan Asen perished fighting bravely for his country.
It seems that despite the great losses the Bulgarians had repulsed the enemy as the next recorded Ottoman invasion occurred 6 years later, in 1355, when in the battle of Ihtiman the Ottoman Turks killed Asen's eldest brother, Michael Asen.
Ivan Asen IV married a Wallachian Princess and had two daughters.
Kaya Alp
Kaya Alp was, according to Ottoman tradition, the son of Kızıl Buğa and the father of Suleyman Shah, who was, in turn, the grandfather of Ertuğrul, and the great grandfather of the Ottoman Empire founder, Osman I.
Kaliman Asen II of Bulgaria
Kaliman Asen II, or commonly, but less accurately Koloman Asen II, ruled as tsar of Bulgaria for a short time in 1256.
The year of his birth is unknown.
Kaliman Asen II was the son of" sebastokrator" Alexander, who was the younger brother of Ivan Asen II of Bulgaria.
Kaliman
Asen II's mother is unknown, and attempts to identify her as a Serbian princess are based on the erroneous identification of Kaliman Asen II with the" sebastokrator" Kaloyan, who was still alive in 1258/ 59.
In 1256 Kaliman Asen murdered his first cousin Michael Asen I during a hunting party in the environs of the capital Tărnovo and usurped the throne.
In the process he married Michael Asen I's widow, the unnamed daughter of Rostislav Mihailovich, but he was unable to maintain himself on the throne.
Rostislav advanced on Tărnovo from Belgrade, and Kaliman Asen II fled the capital.
Rostislav returned home with his daughter and claiming the title of emperor of Bulgaria, while a brother- in- law of Michael Asen I, Mitso Asen took the throne.
In the meantime, Kaliman Asen II had been murdered after being abandoned by most of his supporters.
Kiril, Prince of Preslav
Prince Kyril of Bulgaria, Prince of Preslav (Kyril Heinrich Franz Ludwig Anton Karl Philipp; 17 November 1895 – 1 February 1945) was the second son of Ferdinand I of Bulgaria and his first wife Marie Louise of Bourbon-Parma.
He was a younger brother of Boris III of Bulgaria and a prince regent of the Kingdom of Bulgaria from 1943 to 1944.
Michael Asen IV of Bulgaria
Michail Asen  (c. 1322–1355) was the eldest son of Ivan Alexander of Bulgaria from his marriage with Theodora of Wallachia.
After his father acceded to the throne in 1331, the young prince was proclaimed co-Emperor.
He was to succeed his father under the name Michael IV Asen.
The heir to the throne was the pride of the royal family and was said to possess "all virtues".
He married Maria, renamed Irina, the daughter of Andronikos III Palaiologos.
In 1354–1355 the Ottoman Turks invaded Bulgaria and headed towards Plovdiv and Sofia.
It is mentioned in an anonymous Bulgarian chronicle that Michail Asen gathered the Bulgarians and engaged the Turks near Sofia.
The Bulgarians were defeated and suffered heavy casualties including Michail himself.
But the battle was not in vain: the Ottomans failed to capture the cities and did not attack the country up to 1370.In
the Bulgarian folklore is mentioned that the son of the Emperor perished with the death of the brave.
Abd al-Muttalib
Abd al- Muttalib Shaybah ibn Hashim( c. 497 – 578) was the grandfather of Islamic prophet Muhammad.
Maria-Irene Palaiologina
Irene Palaiologina( Irina; Ειρήνη Παλαιολογίνα)( 1327- after 1356) was a Byzantine princess and Bulgarian empress consort.
She was also known as Maria Palaiologina( Μαρία Παλαιολογίνα).
Her parents were Andronikos III Palaiologos and Anna of Savoy, whilst her siblings were John V Palaiologos and Michael Palaiologos.
She married in 1336 Tsar Michael Asen IV of Bulgaria.
Nothing else is known about her, except that she was an Orthodox Christian.
Ana-Neda
Ana- Neda( Bulgarian and; fl. 1323- 1324) was the Empress consort of Bulgaria briefly in 1323- 1324 as the spouse of" Despot of Vidin" Michael Shishman who was elected as Emperor of Bulgaria in 1323.
She was the daughter of Serbian King Stefan Uroš II Milutin and Princess Ana Terter, daughter of George I of Bulgaria.
From the marriage with Michael, they had three sons, one of whom was Ivan Stephen of Bulgaria, later briefly the Emperor of Bulgaria( 1330 – 1331).
Theodora of Wallachia
Theodora  of Wallachia was the daughter of Basarab I of Wallachia (r. 1310–1352) and Lady Margareta.
She married Ivan Alexander of Bulgaria as his first wife.
This marriage produced four children — Michael Asen, Ivan Sratsimir, Ivan Asen and Vasilisa.
In 1345 Tsar Ivan Alexander divorced Tsaritsa Theodora and sent her into a monastery as a nun under the name Teofana.

Question: Who is Michael Asen Iv Of Bulgaria's maternal grandfather?
Answer: Basarab I of Wallachia