NPASS Natural Product

Natural Product: NPC475455

Natural Product ID:	NPC475455
Common Name:	Swinhoeiamide A
IUPAC Name:	[(2R,3R,5R,7S,8S,9R)-2-[(1R,3S,4S,5R,6R,7E,9E,13Z)-15-amino-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-15-oxopentadeca-7,9,13-trienyl]-7-methoxy-4,4,8-trimethyl-9-[(E)-3-(2-methyl-1,3-oxazol-4-yl)prop-2-enyl]-1,10-dioxaspiro[4.5]decan-3-yl] dihydrogen phosphate
Synonyms:
Molecular Formula:	C40H65N2O12P
Standard InCHIKey:	NWFMVMFBNZSIHF-PKGIXKDLSA-N
Standard InCHI:	InChI=1S/C40H65N2O12P/c1-23(18-35(41)44)14-12-15-24(2)25(3)19-26(4)36(45)27(5)31(43)20-33(49-10)37-38(54-55(46,47)48)39(8,9)40(53-37)21-34(50-11)28(6)32(52-40)17-13-16-30-22-51-29(7)42-30/h13,15-16,18-19,22,26-28,31-34,36-38,43,45H,12,14,17,20-21H2,1-11H3,(H2,41,44)(H2,46,47,48)/b16-13+,23-18-,24-15+,25-19+/t26-,27+,28-,31+,32-,33-,34+,36-,37-,38+,40-/m1/s1
Canonical SMILES:	CO[C@@H]([C@H]1O[C@@]2(C([C@H]1OP(=O)(O)O)(C)C)C[C@H](OC)[C@@H]([C@H](O2)C/C=C/c1coc(n1)C)C)C[C@@H]([C@@H]([C@@H]([C@@H](/C=C(/C(=C/CC/C(=CC(=N)O)/C)/C)C)C)O)C)O
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
NPO22214	Theonella swinhoei	Species	Theonellidae	Eukaryota				PMID[12193024]

Biological Activity

Activity Type	# Activity
LD50	2
MIC	2
Others	2

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	1	ug/ml	7143358
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LD50	=	10	ug	12431049
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LD50	=	0.98	ug	12431049
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	14	mm	18809936
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LC50	=	2.98	ppm	16472241
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1.2	ug/ml	DrugMatrix in vitro pharmacology data

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 NPC475455 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	153
0.1-0.2	877
0.2-0.3	2881
0.3-0.4	16420
0.4-0.5	10299
0.5-0.6	248
0.6-0.7	6
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7778	Intermediate Similarity	NPC211555
0.7746	Intermediate Similarity	NPC12660
0.7719	Intermediate Similarity	NPC186452
0.7701	Intermediate Similarity	NPC54983
0.7072	Intermediate Similarity	NPC30527
0.6443	Remote Similarity	NPC314523
0.6443	Remote Similarity	NPC58001
0.6293	Remote Similarity	NPC476829
0.6018	Remote Similarity	NPC168135
0.6018	Remote Similarity	NPC322800
0.6018	Remote Similarity	NPC477218
0.5973	Remote Similarity	NPC299035
0.5973	Remote Similarity	NPC177432
0.5909	Remote Similarity	NPC309919
0.5909	Remote Similarity	NPC49195
0.5857	Remote Similarity	NPC295653
0.5857	Remote Similarity	NPC107458
0.5841	Remote Similarity	NPC325683
0.5841	Remote Similarity	NPC476832
0.5796	Remote Similarity	NPC37924
0.5752	Remote Similarity	NPC477219
0.5741	Remote Similarity	NPC258022
0.5729	Remote Similarity	NPC127775
0.5708	Remote Similarity	NPC477587
0.5708	Remote Similarity	NPC477589
0.5702	Remote Similarity	NPC476828
0.5699	Remote Similarity	NPC231110
0.5685	Remote Similarity	NPC97078
0.5685	Remote Similarity	NPC470146
0.5685	Remote Similarity	NPC101980
0.5681	Remote Similarity	NPC224395
0.5681	Remote Similarity	NPC208297
0.567	Remote Similarity	NPC312887
0.566	Remote Similarity	NPC477590
0.566	Remote Similarity	NPC477586
0.566	Remote Similarity	NPC477588
0.566	Remote Similarity	NPC477585
0.5654	Remote Similarity	NPC268063
0.5654	Remote Similarity	NPC224609
0.5648	Remote Similarity	NPC52587
0.5619	Remote Similarity	NPC103452
0.5619	Remote Similarity	NPC46313
0.5619	Remote Similarity	NPC199461
0.5614	Remote Similarity	NPC476830
0.5602	Remote Similarity	NPC252616
0.5602	Remote Similarity	NPC45576
0.5602	Remote Similarity	NPC154873
0.5602	Remote Similarity	NPC32583
0.5602	Remote Similarity	NPC109498
0.5602	Remote Similarity	NPC474090
0.5602	Remote Similarity	NPC61667
0.5602	Remote Similarity	NPC163147

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	452
0.2-0.3	1372
0.3-0.4	4511
0.4-0.5	2617
0.5-0.6	76
0.6-0.7	3
0.7-0.8	0
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
0.6667	Remote Similarity	NPD6347	Phase 2
0.655	Remote Similarity	NPD7490	Discontinued
0.6214	Remote Similarity	NPD7896	Approved
0.5991	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD6857	Phase 3
0.56	Remote Similarity	NPD6974	Phase 3

Structure

NPC475455 OpenBabel07101719182D 55 57 0 0 1 0 0 0 0 0999 V2000 -10.0776 0.2729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1431 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1868 1.3124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5396 0.7772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8923 0.2420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4431 -3.1689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2454 -5.6133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4456 -0.6615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7024 0.0076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4752 -3.6817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1295 -0.1853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7612 -1.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0160 -4.9323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4303 -0.2624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7830 -0.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1025 -4.5255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8250 -4.3445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7175 -1.4213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8267 -0.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5540 -1.2443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5115 -1.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2935 -6.1133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4084 -0.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4740 0.1534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4958 0.3614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8486 -0.1739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2013 -0.7091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5295 -2.7622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2454 -5.6133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2935 -5.1133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5322 -1.4522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7205 -3.3500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1151 -1.9875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4250 -1.7677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0483 -2.1645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1794 -0.9170 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0933 -1.7796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7024 -1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0702 -1.9566 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3424 -4.8043 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8412 -2.4033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3573 -3.1155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4885 -1.8681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1939 -2.9385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2340 -1.1799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3424 -6.4223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8070 -2.9432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8364 -2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 7 29 1 0 0 0 0 8 39 1 0 0 0 0 9 39 1 0 0 0 0 10 49 1 0 0 0 0 11 50 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 23 1 0 0 0 0 15 24 2 0 0 0 0 16 30 1 0 0 0 0 18 23 2 0 0 0 0 18 35 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 31 1 0 0 0 0 21 34 1 0 0 0 0 22 30 2 0 0 0 0 22 51 1 0 0 0 0 24 25 1 0 0 0 0 26 4 1 1 0 0 0 26 36 1 0 0 0 0 27 5 1 1 0 0 0 27 31 1 0 0 0 0 27 36 1 0 0 0 0 28 6 1 6 0 0 0 28 32 1 0 0 0 0 28 34 1 0 0 0 0 29 42 2 0 0 0 0 29 51 1 0 0 0 0 30 42 1 0 0 0 0 31 43 1 6 0 0 0 32 17 1 1 0 0 0 32 52 1 0 0 0 0 33 20 1 6 0 0 0 33 49 1 0 0 0 0 34 50 1 6 0 0 0 35 41 2 0 0 0 0 35 44 1 0 0 0 0 36 45 1 6 0 0 0 37 33 1 6 0 0 0 37 38 1 0 0 0 0 37 53 1 0 0 0 0 38 39 1 0 0 0 0 38 54 1 6 0 0 0 39 40 1 0 0 0 0 40 21 1 1 0 0 0 40 52 1 0 0 0 0 40 53 1 0 0 0 0 46 55 1 0 0 0 0 47 55 1 0 0 0 0 48 55 2 0 0 0 0 54 55 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	643644
ChEMBL	CHEMBL505968
ZINC

Physicochemical Properties

Molecular Weight:	796.43
ALogP:	2.17
MLogP:	4.21
XLogP:	4.52
# Rotatable Bonds:	35
Polar Surface Area:	224.06
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	55

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Structure MOL file
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