NPASS Natural Product

Natural Product: NPC295228

Natural Product ID:	NPC295228
Common Name:	1',2', 3',4'-Tetradehydrotubulosine
IUPAC Name:	1-[[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-9H-pyrido[3,4-b]indol-6-ol
Synonyms:	1',2',3',4'-Tetradehydrotubulosine
Molecular Formula:	C29H33N3O3
Standard InCHIKey:	FYIJNEXYFHEJLZ-IAKTWSEQSA-N
Standard InCHI:	InChI=1S/C29H33N3O3/c1-4-17-16-32-10-8-18-13-27(34-2)28(35-3)15-22(18)26(32)12-19(17)11-25-29-21(7-9-30-25)23-14-20(33)5-6-24(23)31-29/h5-7,9,13-15,17,19,26,31,33H,4,8,10-12,16H2,1-3H3/t17-,19-,26-/m0/s1
Canonical SMILES:	CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1Cc1nccc2c1[nH]c1c2cc(cc1)O)cc(c(c3)OC)OC
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
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota				PMID[10514334]

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Biological Activity

Activity Type	# Activity
ED50	10

Activity Type	# Activity
Cell Line	9
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	3.6	ug/ml	20194693
NPT136	Cell Line	SK-N-SH	Homo sapiens	ED50	=	4	ug/ml	24775914
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	2.8	ug/ml	24775914
NPT2	Others	Unspecified		ED50	=	3.9	ug/ml	20194693
NPT2345	Cell Line	SW626	Homo sapiens	ED50	=	6.1	ug/ml	24780599
NPT726	Cell Line	M109	Mus musculus	ED50	=	4.4	ug/ml	24775914
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	6.8	ug/ml	19734910
NPT91	Cell Line	KB	Homo sapiens	ED50	=	8.8	ug/ml	17417631
NPT91	Cell Line	KB	Homo sapiens	ED50	=	9	ug/ml	24775914
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.2	ug/ml	24775914

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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 NPC295228 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	467
0.1-0.2	2389
0.2-0.3	10227
0.3-0.4	4516
0.4-0.5	9476
0.5-0.6	1909
0.6-0.7	1492
0.7-0.8	354
0.8-0.85	50
0.85-0.9	8
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7397	Intermediate Similarity	NPC478081
0.7399	Intermediate Similarity	NPC53144
0.7399	Intermediate Similarity	NPC162484
0.7403	Intermediate Similarity	NPC292958
0.7403	Intermediate Similarity	NPC473179

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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 NPC295228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	669
0.2-0.3	1041
0.3-0.4	1382
0.4-0.5	2533
0.5-0.6	2085
0.6-0.7	967
0.7-0.8	185
0.8-0.85	22
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7021	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4989	Phase 2
0.7022	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4996	Approved
0.7025	Intermediate Similarity	NPD4995	Approved

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Structure

NPC295228 OpenBabel07101719142D 35 40 0 0 1 0 0 0 0 0999 V2000 2.7210 3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 -4.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -3.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 3.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5870 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 -2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 -1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 2.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7210 -1.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5823 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 -0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8549 -2.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 -2.3309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 2.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 0.6691 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -2.1701 -3.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8549 -3.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -2.8309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 5 6 2 0 0 0 0 5 20 1 0 0 0 0 6 24 1 0 0 0 0 7 9 1 0 0 0 0 7 21 2 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 30 2 0 0 0 0 10 32 1 0 0 0 0 11 25 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 18 2 0 0 0 0 13 27 1 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 15 22 2 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 32 1 0 0 0 0 17 4 1 1 0 0 0 17 19 1 0 0 0 0 18 22 1 0 0 0 0 19 11 1 6 0 0 0 20 33 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 23 24 2 0 0 0 0 24 31 1 0 0 0 0 25 29 2 0 0 0 0 25 30 1 0 0 0 0 26 32 1 6 0 0 0 27 28 2 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 29 31 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	21668793
ChEMBL	CHEMBL481241
ZINC

Physicochemical Properties

Molecular Weight:	471.25
ALogP:	-1.2736
MLogP:	3.99
XLogP:	4.447
# Rotatable Bonds:	9
Polar Surface Area:	70.61
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	35

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