NPASS Natural Product

Natural Product: NPC111323

Natural Product ID:	NPC111323
Common Name:	Cucurbitacin I
IUPAC Name:	(8S,9R,10R,13R,14S,16R,17R)-17-[(E,2R)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:	NSC-521777
Molecular Formula:	C30H42O7
Standard InCHIKey:	NISPVUDLMHQFRQ-MKIKIEMVSA-N
Standard InCHI:	InChI=1S/C30H42O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-13,17,19-20,23,31-32,36-37H,10,14-15H2,1-8H3/b12-11+/t17-,19-,20+,23+,27+,28-,29+,30+/m1/s1
Canonical SMILES:	OC1=C[C@@H]2C(=CC[C@@H]3[C@@]2(C)C(=O)C[C@]2([C@@]3(C)C[C@H]([C@@H]2[C@](C(=O)/C=C/C(O)(C)C)(O)C)O)C)C(C1=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
NPO16511	Iberis amara	Species	Brassicaceae	Eukaryota	TCM_Taiwan*
NPO32449	eleaocarpus chinensis	Species	NA	NA	PMID[22239601]
NPO32650	conobea scoparioides	Species	Plantaginaceae	Eukaryota	PMID[7852999]

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Biological Activity

Activity Type	# Activity
EC50	3
GI50	130
IC50	12
Others	12

Activity Type	# Activity
Cell Line	144
Individual Protein	1
Organism	1
Others	11

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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	GI50		841.4	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		503.5	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		1879.32	nM	PubChem BioAssay data set
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50		1610.65	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.1	nM	20347305
NPT116	Cell Line	HL-60	Homo sapiens	GI50		683.91	nM	PubChem BioAssay data set
NPT116	Cell Line	HL-60	Homo sapiens	GI50		265.46	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		538.27	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	GI50		321.37	nM	PubChem BioAssay data set
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	190	nM	22239601

Showing 1 to 10 of 154 entries

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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 NPC111323 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	140
0.1-0.2	802
0.2-0.3	2755
0.3-0.4	6260
0.4-0.5	9625
0.5-0.6	5347
0.6-0.7	4249
0.7-0.8	1470
0.8-0.85	195
0.85-0.9	39
0.9-0.95	5
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.8039	Intermediate Similarity	NPC40765
0.8039	Intermediate Similarity	NPC192428
0.8041	Intermediate Similarity	NPC51014
0.8041	Intermediate Similarity	NPC474778
0.8041	Intermediate Similarity	NPC474733

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 NPC111323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1244
0.2-0.3	3566
0.3-0.4	2786
0.4-0.5	889
0.5-0.6	200
0.6-0.7	155
0.7-0.8	119
0.8-0.85	47
0.85-0.9	13
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6852	Remote Similarity	NPD5282	Discontinued
0.6857	Remote Similarity	NPD5208	Approved
0.688	Remote Similarity	NPD8293	Discontinued
0.69	Remote Similarity	NPD4819	Approved
0.69	Remote Similarity	NPD5368	Approved

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Structure

CID111323 OpenBabel06191715462D 37 40 0 0 1 0 0 0 0 0999 V2000 5.0858 -3.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1814 -2.8806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2974 3.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1512 3.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5027 0.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0231 -2.3562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6493 2.8540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8249 2.3784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3211 -1.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2510 -1.5378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2966 0.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6470 0.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8241 -0.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4733 2.3779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4731 1.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1204 1.4258 0.0000 C 0 0 0 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 -0.8246 1.4267 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6846 -1.0299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6484 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8244 -0.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1206 2.3775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8876 -2.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2971 2.8536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9511 0.0000 C 0 0 2 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 -1.6487 0.9506 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8249 -1.4263 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9744 0.9324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5017 -0.4922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9778 -0.1255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5024 -0.4938 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9663 2.8652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8174 -2.0458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1188 -2.0629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 6 0 0 0 18 24 1 0 0 0 0 18 31 1 0 0 0 0 19 23 1 0 0 0 0 19 32 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 21 33 2 0 0 0 0 22 29 1 0 0 0 0 22 34 2 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 35 2 0 0 0 0 25 36 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 1 0 0 0 30 37 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281321
ChEMBL	CHEMBL387737
ZINC

Physicochemical Properties

Molecular Weight:	514.29
ALogP:	0.7877
MLogP:	3.99
XLogP:	2.664
# Rotatable Bonds:	16
Polar Surface Area:	132.13
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	37

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