NPASS Natural Product

Natural Product: NPC104387

Natural Product ID:	NPC104387
Common Name:	Calenduladiol
IUPAC Name:	(1R,3aS,4S,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-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-4,9-diol
Synonyms:	Calenduladiol
Molecular Formula:	C30H50O2
Standard InCHIKey:	AJBZENLMTKDAEK-SKESNUHASA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-18(2)19-11-14-28(6)24(32)17-30(8)20(25(19)28)9-10-22-27(5)15-13-23(31)26(3,4)21(27)12-16-29(22,30)7/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20+,21-,22+,23-,24-,25+,27-,28+,29+,30+/m0/s1
Canonical SMILES:	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)C[C@@H]2O)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)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
NPO1019	Citrus hybr	Species	Rutaceae	Eukaryota	UNPD*
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	UNPD*
NPO11413	Incarvillea emodi	Species	Bignoniaceae	Eukaryota	UNPD*
NPO11702	Plexaurella grisea	Species	Plexauridae	Eukaryota	UNPD*
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	UNPD*
NPO12087	Amaioua guianensis	Species	Rubiaceae	Eukaryota	UNPD*
NPO13130	Notholaena peninsularis	Species	Pteridaceae	Eukaryota	UNPD*
NPO13296	Pinus sitchensis	Species	Pinaceae	Eukaryota	UNPD*
NPO13410	Mcneillia graminifolia	Species	Caryophyllaceae	Eukaryota	UNPD*
NPO1354	Myelochroa rhytidodes	Species	Parmeliaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
GI50	51
IC50	4
Others	2

Activity Type	# Activity
Cell Line	53
Individual Protein	4

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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	=	31440	nM	17125233
NPT111	Cell Line	K562	Homo sapiens	GI50		6606.93	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		11220.18	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		19543.39	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		24434.31	nM	PubChem BioAssay data set
NPT148	Cell Line	HCT-15	Homo sapiens	GI50		18535.32	nM	PubChem BioAssay data set
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50		100000	nM	PubChem BioAssay data set
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	Inhibition	=	8.1	%	24835788
NPT2668	Individual Protein	Acetylcholinesterase	Torpedo californica	IC50	>	200000	nM	24835788
NPT306	Cell Line	PC-3	Homo sapiens	GI50		39445.73	nM	PubChem BioAssay data set

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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 NPC104387 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	90
0.1-0.2	1183
0.2-0.3	5045
0.3-0.4	12361
0.4-0.5	4493
0.5-0.6	3447
0.6-0.7	2863
0.7-0.8	1032
0.8-0.85	214
0.85-0.9	105
0.9-0.95	37
0.95-1	19

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Similarity Score	Similarity Level	Natural Product ID
0.84	Intermediate Similarity	NPC285893
0.84	Intermediate Similarity	NPC28657
0.84	Intermediate Similarity	NPC136188
0.84	Intermediate Similarity	NPC304309
0.84	Intermediate Similarity	NPC230301

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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 NPC104387 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	125
0.1-0.2	1920
0.2-0.3	4352
0.3-0.4	2004
0.4-0.5	352
0.5-0.6	177
0.6-0.7	172
0.7-0.8	53
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.619	Remote Similarity	NPD5169	Approved
0.619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5251	Approved
0.619	Remote Similarity	NPD5135	Approved
0.619	Remote Similarity	NPD5247	Approved

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Structure

CID104387 OpenBabel06191715452D 32 36 0 0 1 0 0 0 0 0999 V2000 -4.8843 -0.8188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3534 -1.4060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2620 -1.8924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7707 -1.0426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7962 -2.3821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6412 1.9215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8199 1.4774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8446 0.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8199 -1.4210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.8944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2804 0.9457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4600 -0.4729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4613 -3.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4614 1.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6412 -2.8407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6401 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9493 -0.6705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2802 -0.0009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8202 -0.4738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4602 -1.4201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8207 -1.4206 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2810 -2.8397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8207 1.4200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6407 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2804 -1.8930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6406 -1.8939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6409 0.9462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8205 -0.4734 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 4.1313 -3.3300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8210 2.3929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 24 1 0 0 0 0 17 30 1 0 0 0 0 19 18 1 6 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 20 30 1 6 0 0 0 21 26 1 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 28 1 1 0 0 0 24 32 1 0 0 0 0 25 28 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	461835
ChEMBL	CHEMBL462795
ZINC

Physicochemical Properties

Molecular Weight:	442.38
ALogP:	2.6582
MLogP:	4.54
XLogP:	9.394
# Rotatable Bonds:	10
Polar Surface Area:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	32

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