NPASS Natural Product

Natural Product: NPC176246

Natural Product ID:	NPC176246
Common Name:	Grincamycin B
IUPAC Name:	(3R)-4-[1,5-dihydroxy-6-[(2R,4R,5S,6R)-4-hydroxy-6-methyl-5-[(2S,5S,6S)-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxyoxan-2-yl]-9,10-dioxoanthracen-2-yl]-3-methyl-3-[(2S,5S,6S)-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxybutanoic acid
Synonyms:	Grincamycin B
Molecular Formula:	C49H62O18
Standard InCHIKey:	FMPNXDMJKBQLJR-SVDKGFTASA-N
Standard InCHI:	InChI=1S/C49H62O18/c1-22-31(50)11-15-38(60-22)64-34-13-17-40(62-24(34)3)66-48-26(5)59-36(19-33(48)52)28-9-10-30-43(45(28)56)47(58)29-8-7-27(44(55)42(29)46(30)57)20-49(6,21-37(53)54)67-41-18-14-35(25(4)63-41)65-39-16-12-32(51)23(2)61-39/h7-10,22-26,33-36,38-41,48,52,55-56H,11-21H2,1-6H3,(H,53,54)/t22-,23-,24-,25-,26+,33+,34-,35-,36+,38-,39-,40-,41-,48+,49+/m0/s1
Canonical SMILES:	OC(=O)C[C@@](Cc1ccc2c(c1O)C(=O)c1c(C2=O)c(O)c(cc1)[C@H]1C[C@@H](O)[C@@H]([C@H](O1)C)O[C@H]1CC[C@@H]([C@@H](O1)C)O[C@H]1CCC(=O)[C@@H](O1)C)(O[C@H]1CC[C@@H]([C@@H](O1)C)O[C@H]1CCC(=O)[C@@H](O1)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	Isolation Part	Collection Location	Collection Time	Reference
NPO1930.2	Streptomyces lusitanus scsio lr32	Subspecies	Streptomycetaceae	Bacteria				PMID[22304344]

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Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1312	Cell Line	SW1990	Homo sapiens	IC50	=	11000	nM	17517504
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	6400	nM	22071302
NPT319	Cell Line	B16	Mus musculus	IC50	=	2100	nM	23064162
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	100000	nM	19223619
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8500	nM	20666364
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12000	nM	26191359

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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 NPC176246 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	309
0.1-0.2	1176
0.2-0.3	2188
0.3-0.4	4620
0.4-0.5	6922
0.5-0.6	5695
0.6-0.7	5160
0.7-0.8	4396
0.8-0.85	325
0.85-0.9	73
0.9-0.95	22
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.8202	Intermediate Similarity	NPC154986
0.8202	Intermediate Similarity	NPC124828
0.8208	Intermediate Similarity	NPC317544
0.8208	Intermediate Similarity	NPC69868
0.8212	Intermediate Similarity	NPC231787

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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 NPC176246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	875
0.2-0.3	1653
0.3-0.4	2726
0.4-0.5	2169
0.5-0.6	1005
0.6-0.7	281
0.7-0.8	94
0.8-0.85	26
0.85-0.9	6
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.658	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4955	Approved
0.6582	Remote Similarity	NPD5028	Approved
0.6582	Remote Similarity	NPD36	Approved
0.6582	Remote Similarity	NPD4954	Approved

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Structure

NPC176246 OpenBabel07101718242D 67 74 0 0 1 0 0 0 0 0999 V2000 2.5981 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8301 -4.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 -2.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3301 -1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8301 -1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3301 -1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -10.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3301 -3.6962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -7.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.9641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8301 -2.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -7.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3301 -1.9641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -9.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8301 -2.8301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -10.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8301 -2.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -10.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3301 -3.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 -1.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8301 -2.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7 8 2 0 0 0 0 7 27 1 0 0 0 0 8 29 1 0 0 0 0 9 10 2 0 0 0 0 9 28 1 0 0 0 0 10 30 1 0 0 0 0 11 15 1 0 0 0 0 11 31 1 0 0 0 0 12 16 1 0 0 0 0 12 32 1 0 0 0 0 13 17 1 0 0 0 0 13 34 1 0 0 0 0 14 18 1 0 0 0 0 14 35 1 0 0 0 0 15 38 1 0 0 0 0 16 39 1 0 0 0 0 17 40 1 0 0 0 0 18 41 1 0 0 0 0 19 33 1 0 0 0 0 19 36 1 0 0 0 0 20 27 1 0 0 0 0 20 49 1 0 0 0 0 21 37 1 0 0 0 0 21 49 1 0 0 0 0 22 1 1 1 0 0 0 22 31 1 0 0 0 0 22 60 1 0 0 0 0 23 2 1 1 0 0 0 23 32 1 0 0 0 0 23 61 1 0 0 0 0 24 3 1 1 0 0 0 24 34 1 0 0 0 0 24 62 1 0 0 0 0 25 4 1 1 0 0 0 25 35 1 0 0 0 0 25 63 1 0 0 0 0 26 5 1 1 0 0 0 26 48 1 0 0 0 0 26 59 1 0 0 0 0 27 44 2 0 0 0 0 28 45 2 0 0 0 0 29 42 2 0 0 0 0 29 47 1 0 0 0 0 30 43 2 0 0 0 0 30 46 1 0 0 0 0 31 50 2 0 0 0 0 32 51 2 0 0 0 0 33 48 1 0 0 0 0 33 52 1 1 0 0 0 34 64 1 1 0 0 0 35 65 1 1 0 0 0 36 28 1 1 0 0 0 36 59 1 0 0 0 0 37 53 2 0 0 0 0 37 54 1 0 0 0 0 38 60 1 0 0 0 0 38 64 1 6 0 0 0 39 61 1 0 0 0 0 39 65 1 6 0 0 0 40 62 1 0 0 0 0 40 66 1 6 0 0 0 41 63 1 0 0 0 0 41 67 1 6 0 0 0 42 44 1 0 0 0 0 42 46 1 0 0 0 0 43 45 1 0 0 0 0 43 47 1 0 0 0 0 44 55 1 0 0 0 0 45 56 1 0 0 0 0 46 57 2 0 0 0 0 47 58 2 0 0 0 0 48 66 1 6 0 0 0 49 6 1 6 0 0 0 49 67 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	57332649
ChEMBL	CHEMBL2011810
ZINC

Physicochemical Properties

Molecular Weight:	938.39
ALogP:	-5.4307
MLogP:	4.87
XLogP:	2.338
# Rotatable Bonds:	23
Polar Surface Area:	249.34
# H-Bond Aceptor:	16
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	67

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