NPASS Natural Product

Natural Product: NPC79367

Natural Product ID:	NPC79367
Common Name:	Penasin B
IUPAC Name:	(2S,3S,4S)-4-amino-2-[(5Z,9Z)-9-chlorohexacosa-5,9-dienyl]oxolan-3-ol
Synonyms:	Penasin B
Molecular Formula:	C30H56ClNO2
Standard InCHIKey:	MOBARKDTJFXOAP-BDGGXDINSA-N
Standard InCHI:	InChI=1S/C30H56ClNO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-20-23-27(31)24-21-18-15-16-19-22-25-29-30(33)28(32)26-34-29/h15,18,23,28-30,33H,2-14,16-17,19-22,24-26,32H2,1H3/b18-15-,27-23-/t28-,29-,30-/m0/s1
Canonical SMILES:	CCCCCCCCCCCCCCCC/C=C(/CC/C=CCCCC[C@@H]1OC[C@@H]([C@@H]1O)N)Cl
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO31241	Penares	Genus	Geodiidae	Eukaryota				PMID[20949915]

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	10	ug/ml	20949915
NPT168	Cell Line	P388	Mus musculus	IC50	=	50	ug/ml	20949915

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 NPC79367 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	33
0.1-0.2	336
0.2-0.3	12144
0.3-0.4	12725
0.4-0.5	4961
0.5-0.6	620
0.6-0.7	56
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9324	High Similarity	NPC3094
0.7763	Intermediate Similarity	NPC113224
0.7703	Intermediate Similarity	NPC17455
0.7703	Intermediate Similarity	NPC47333
0.7654	Intermediate Similarity	NPC51055
0.7654	Intermediate Similarity	NPC140327
0.7654	Intermediate Similarity	NPC62293
0.7654	Intermediate Similarity	NPC212008
0.7209	Intermediate Similarity	NPC207657
0.7162	Intermediate Similarity	NPC168308
0.7162	Intermediate Similarity	NPC302569
0.7143	Intermediate Similarity	NPC55068
0.7024	Intermediate Similarity	NPC264417
0.7024	Intermediate Similarity	NPC217095
0.6977	Remote Similarity	NPC474833
0.68	Remote Similarity	NPC8979
0.6782	Remote Similarity	NPC473972
0.6782	Remote Similarity	NPC473971
0.6782	Remote Similarity	NPC475363
0.6588	Remote Similarity	NPC305223
0.6562	Remote Similarity	NPC475603
0.6562	Remote Similarity	NPC61894
0.6548	Remote Similarity	NPC324638
0.6512	Remote Similarity	NPC477422
0.6512	Remote Similarity	NPC288086
0.6486	Remote Similarity	NPC123814
0.6429	Remote Similarity	NPC291196
0.6429	Remote Similarity	NPC103712
0.6354	Remote Similarity	NPC39290
0.6354	Remote Similarity	NPC159369
0.6344	Remote Similarity	NPC477199
0.631	Remote Similarity	NPC474812
0.6267	Remote Similarity	NPC474322
0.6235	Remote Similarity	NPC475930
0.6235	Remote Similarity	NPC127145
0.6207	Remote Similarity	NPC26932
0.6163	Remote Similarity	NPC474674
0.6154	Remote Similarity	NPC314762
0.6136	Remote Similarity	NPC473588
0.6136	Remote Similarity	NPC78562
0.6129	Remote Similarity	NPC474312
0.6125	Remote Similarity	NPC325550
0.6125	Remote Similarity	NPC329003
0.6125	Remote Similarity	NPC326524
0.6122	Remote Similarity	NPC139782
0.6122	Remote Similarity	NPC74672
0.6122	Remote Similarity	NPC43074
0.6122	Remote Similarity	NPC209047
0.6122	Remote Similarity	NPC242503
0.6061	Remote Similarity	NPC263545
0.6061	Remote Similarity	NPC15851
0.6061	Remote Similarity	NPC186840
0.6061	Remote Similarity	NPC475125
0.6061	Remote Similarity	NPC473581
0.6061	Remote Similarity	NPC473950
0.6061	Remote Similarity	NPC309898
0.6061	Remote Similarity	NPC473604
0.6061	Remote Similarity	NPC111567
0.6047	Remote Similarity	NPC474675
0.6047	Remote Similarity	NPC137620
0.6042	Remote Similarity	NPC258824
0.6019	Remote Similarity	NPC315170
0.6	Remote Similarity	NPC477198
0.6	Remote Similarity	NPC22101
0.6	Remote Similarity	NPC127091
0.6	Remote Similarity	NPC330426
0.6	Remote Similarity	NPC321030
0.6	Remote Similarity	NPC271921
0.6	Remote Similarity	NPC104537
0.6	Remote Similarity	NPC148192
0.5946	Remote Similarity	NPC96966
0.5946	Remote Similarity	NPC121062
0.5946	Remote Similarity	NPC29222
0.5941	Remote Similarity	NPC156782
0.5941	Remote Similarity	NPC256570
0.5941	Remote Similarity	NPC3568
0.5941	Remote Similarity	NPC54961
0.5941	Remote Similarity	NPC282088
0.5941	Remote Similarity	NPC157353
0.5941	Remote Similarity	NPC192066
0.5941	Remote Similarity	NPC158445
0.5941	Remote Similarity	NPC17290
0.593	Remote Similarity	NPC48218
0.593	Remote Similarity	NPC141481
0.593	Remote Similarity	NPC473559
0.593	Remote Similarity	NPC324981
0.5926	Remote Similarity	NPC319131
0.5909	Remote Similarity	NPC474468
0.59	Remote Similarity	NPC182632
0.59	Remote Similarity	NPC282705
0.5895	Remote Similarity	NPC178758
0.5895	Remote Similarity	NPC196102
0.5895	Remote Similarity	NPC228638
0.5882	Remote Similarity	NPC476261
0.5882	Remote Similarity	NPC25033
0.5882	Remote Similarity	NPC470382
0.5882	Remote Similarity	NPC471635
0.5882	Remote Similarity	NPC119225
0.5882	Remote Similarity	NPC83965
0.5862	Remote Similarity	NPC475694
0.5862	Remote Similarity	NPC473710
0.5862	Remote Similarity	NPC16964
0.5843	Remote Similarity	NPC476709
0.5833	Remote Similarity	NPC475918
0.5825	Remote Similarity	NPC8098
0.5825	Remote Similarity	NPC183449
0.5825	Remote Similarity	NPC197294
0.5814	Remote Similarity	NPC475443
0.5814	Remote Similarity	NPC473829
0.5804	Remote Similarity	NPC314306
0.5795	Remote Similarity	NPC476696
0.5795	Remote Similarity	NPC476695
0.5795	Remote Similarity	NPC476694
0.5795	Remote Similarity	NPC476660
0.5795	Remote Similarity	NPC97614
0.5784	Remote Similarity	NPC262312
0.5784	Remote Similarity	NPC35269
0.5784	Remote Similarity	NPC23454
0.5784	Remote Similarity	NPC70323
0.5765	Remote Similarity	NPC476654
0.5765	Remote Similarity	NPC476657
0.5765	Remote Similarity	NPC476655
0.5747	Remote Similarity	NPC23721
0.5741	Remote Similarity	NPC477001
0.5741	Remote Similarity	NPC477000
0.5741	Remote Similarity	NPC74035
0.5714	Remote Similarity	NPC477421
0.5699	Remote Similarity	NPC11796
0.5699	Remote Similarity	NPC218817
0.5698	Remote Similarity	NPC476659
0.5698	Remote Similarity	NPC476656
0.5684	Remote Similarity	NPC82799
0.5682	Remote Similarity	NPC472947
0.5682	Remote Similarity	NPC473772
0.5679	Remote Similarity	NPC52012
0.5679	Remote Similarity	NPC474577
0.5676	Remote Similarity	NPC76976
0.5673	Remote Similarity	NPC45313
0.5673	Remote Similarity	NPC175614
0.5667	Remote Similarity	NPC55652
0.5667	Remote Similarity	NPC314678
0.5663	Remote Similarity	NPC81896
0.5663	Remote Similarity	NPC321919
0.5647	Remote Similarity	NPC476658
0.5647	Remote Similarity	NPC474928
0.5641	Remote Similarity	NPC49494
0.5641	Remote Similarity	NPC188341
0.5632	Remote Similarity	NPC473357
0.5632	Remote Similarity	NPC193029
0.5632	Remote Similarity	NPC470663
0.563	Remote Similarity	NPC478138
0.5625	Remote Similarity	NPC242930
0.5618	Remote Similarity	NPC315199
0.5618	Remote Similarity	NPC42526
0.5618	Remote Similarity	NPC129630
0.5604	Remote Similarity	NPC470992
0.5604	Remote Similarity	NPC474321
0.5604	Remote Similarity	NPC470993

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC79367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	55
0.1-0.2	369
0.2-0.3	4661
0.3-0.4	3149
0.4-0.5	860
0.5-0.6	62
0.6-0.7	4
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7143	Intermediate Similarity	NPD3210	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3212	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3215	Phase 1
0.6216	Remote Similarity	NPD3214	Discontinued
0.6122	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.587	Remote Similarity	NPD3732	Approved
0.5804	Remote Similarity	NPD6430	Approved
0.5804	Remote Similarity	NPD6429	Approved
0.5652	Remote Similarity	NPD818	Approved
0.5652	Remote Similarity	NPD819	Approved

Structure

CID79367 OpenBabel06191715412D 34 34 0 0 1 0 0 0 0 0999 V2000 -9.5498 -17.7808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5008 -17.4718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7087 -16.4936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9656 -15.8245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1735 -14.8464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4303 -14.1772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6383 -13.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8951 -12.5299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1030 -11.5518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3599 -10.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5678 -9.9045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8246 -9.2354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0326 -8.2572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2894 -7.5881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1485 -0.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1974 -1.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4973 -6.6100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8916 -1.6681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4543 -0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7542 -5.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6837 -2.6463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5032 -0.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9621 -4.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4269 -3.3154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2189 -4.2936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2679 -4.6026 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.0878 -2.3479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 -2.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 23 27 2 0 0 0 0 24 27 1 0 0 0 0 26 28 1 0 0 0 0 26 34 1 0 0 0 0 27 31 1 0 0 0 0 28 30 1 0 0 0 0 28 32 1 6 0 0 0 29 25 1 6 0 0 0 29 30 1 0 0 0 0 29 34 1 0 0 0 0 30 33 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	50901044
ChEMBL	CHEMBL1641874
ZINC

Physicochemical Properties

Molecular Weight:	497.40
ALogP:	-4.0219
MLogP:	4.32
XLogP:	11.462
# Rotatable Bonds:	27
Polar Surface Area:	55.48
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	34

Download Data

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General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
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