NPASS Natural Product

Natural Product: NPC4309

Natural Product ID:	NPC4309
Common Name:	3-Acetylbetulinic Acid
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:	(3-O-Acetyl)Betulinic Acid; 3-Acetylbetulinic Acid; 3-O-Acetyl Betulinic Acid; Betulinic Acid 3-O-Acetate
Molecular Formula:	C32H50O4
Standard InCHIKey:	ACWNTJJUZAIOLW-BWXYOZBYSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-19(2)21-11-16-32(27(34)35)18-17-30(7)22(26(21)32)9-10-24-29(6)14-13-25(36-20(3)33)28(4,5)23(29)12-15-31(24,30)8/h21-26H,1,9-18H2,2-8H3,(H,34,35)/t21-,22+,23-,24+,25-,26+,29-,30+,31+,32-/m0/s1
Canonical SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@]1([C@@H]2[C@@H](CC1)C(=C)C)C(=O)O)C)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10450	Clerodendrum infortunatum	Species	Lamiaceae	Eukaryota	UNPD*
NPO1244	Trimusculus conica	Species	Trimusculidae	Eukaryota	UNPD*
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	UNPD*
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	UNPD*
NPO15684	Bipolaris maydis	Species	Pleosporaceae	Eukaryota	UNPD*
NPO1659	Primula denticulata	Species	Primulaceae	Eukaryota	UNPD*
NPO16714	Campanula pendula	Species	Campanulaceae	Eukaryota	UNPD*
NPO1814	Euphorbia cattimandoo	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO1977	Arum montanum	Species	Araceae	Eukaryota	UNPD*
NPO2270	Euptelea polyandra	Species	Eupteleaceae	Eukaryota	PMID[2832544]

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Biological Activity

Activity Type	# Activity
EC50	8
GI50	4
IC50	18
Others	10

Activity Type	# Activity
Cell Line	27
Individual Protein	2
Organism	1
Others	10

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	19000	nM	15270560
NPT111	Cell Line	K562	Homo sapiens	IC50	=	18000	nM	15270560
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	24000	nM	15270560
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	16140	nM	20472329
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	>	3900	nM	11527742
NPT147	Cell Line	SK-MEL-2	Homo sapiens	EC50	>	6900000	nM	11527742
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	18990	nM	20472329
NPT179	Cell Line	A2780	Homo sapiens	EC50	=	18300	nM	26547057
NPT2	Others	Unspecified		Activity	=	0	%	2832544
NPT2	Others	Unspecified		Activity	=	100	%	2832544

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Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC4309 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	888
0.2-0.3	3461
0.3-0.4	10093
0.4-0.5	6147
0.5-0.6	3686
0.6-0.7	3839
0.7-0.8	2194
0.8-0.85	361
0.85-0.9	66
0.9-0.95	21
0.95-1	10

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Similarity Score	Similarity Level	Natural Product ID
0.828	Intermediate Similarity	NPC288906
0.828	Intermediate Similarity	NPC470232
0.828	Intermediate Similarity	NPC84383
0.828	Intermediate Similarity	NPC263135
0.828	Intermediate Similarity	NPC266431

Showing 1 to 5 of 200 entries

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC4309 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1582
0.2-0.3	3863
0.3-0.4	2389
0.4-0.5	661
0.5-0.6	212
0.6-0.7	208
0.7-0.8	94
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6552	Remote Similarity	NPD8377	Approved
0.6552	Remote Similarity	NPD8294	Approved
0.6555	Remote Similarity	NPD6336	Discontinued

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Structure

CID4309 OpenBabel06191715322D 36 40 0 0 1 0 0 0 0 0999 V2000 -5.7278 -0.3469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1908 -0.9364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4716 -4.3471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4555 -1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9622 -0.5716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0249 -1.9168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8732 1.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6470 -0.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8232 -1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1175 1.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6461 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6475 -2.8517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8240 -2.3769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8229 0.4758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2951 1.9005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8241 1.4257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6478 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7891 -0.1979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3248 -3.8538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1172 0.4743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6473 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6464 -0.9506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4704 -2.3759 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4711 0.4748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4716 2.3757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4699 -1.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8235 -1.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8238 0.4753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4714 1.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1786 -4.3461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5678 2.6697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1781 3.0115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3243 -2.8682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 18 1 0 0 0 0 17 30 1 0 0 0 0 18 32 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 19 1 6 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 22 30 1 6 0 0 0 23 28 1 0 0 0 0 23 29 1 1 0 0 0 24 29 1 1 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 36 1 1 0 0 0 26 32 1 1 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 1 0 0 0 31 8 1 1 0 0 0 32 27 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	10300534
ChEMBL	CHEMBL312687
ZINC

Physicochemical Properties

Molecular Weight:	498.37
ALogP:	2.7286
MLogP:	4.54
XLogP:	10.147
# Rotatable Bonds:	12
Polar Surface Area:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	36

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