NPASS Compound

Structure

NPC273185 OpenBabel07101718312D 42 42 0 0 1 0 0 0 0 0999 V2000 12.5290 3.6225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1395 9.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2194 7.9479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6098 3.4763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8238 2.6669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1436 1.9339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1687 2.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4885 1.4233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5136 1.6459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8334 0.9128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8585 1.1353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1783 0.4023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2034 0.6248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5232 -0.1083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5483 0.1143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8681 -0.6188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4933 7.6897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4010 1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3442 6.7009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2885 8.3132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6235 0.7818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4010 1.7568 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1261 6.0774 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8932 -0.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9770 5.0886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0462 4.7233 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1029 3.7344 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0338 3.3691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1828 2.3802 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 2.0569 6.4428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2130 -1.1293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7589 4.4651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7357 5.3467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8156 3.9926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5984 0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6789 3.1109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5984 0.5593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 34 1 0 0 0 0 5 41 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 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 27 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 24 1 0 0 0 0 22 34 1 0 0 0 0 24 42 1 6 0 0 0 25 32 1 0 0 0 0 25 33 1 1 0 0 0 26 28 1 0 0 0 0 26 35 1 1 0 0 0 27 36 2 0 0 0 0 27 42 1 0 0 0 0 28 29 1 0 0 0 0 28 37 1 6 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 31 1 1 0 0 0 30 41 1 0 0 0 0 31 33 2 3 0 0 0 31 39 1 0 0 0 0 32 34 1 0 0 0 0 32 40 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	598.42
Volume:	635.241
LogP:	4.547
LogD:	4.09
LogS:	-4.284
# Rotatable Bonds:	23
TPSA:	145.63
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	4.477
Fsp3:	0.844
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.909
MDCK Permeability:	1.938458444783464e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.826
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	95.42847442626953%
Volume Distribution (VD):	0.912
Pgp-substrate:	2.4548375606536865%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.365
CYP2C9-inhibitor:	0.261
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	3.158
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.588
Drug-inuced Liver Injury (DILI):	0.156
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.516
Maximum Recommended Daily Dose:	0.197
Skin Sensitization:	0.295
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.068

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC273185

Natural Product ID:	NPC273185
*Common Name:**	Bengamide B
IUPAC Name:	[(3S,6S)-1-methyl-7-oxo-6-[[(E,2R,3R,4S,5R)-3,4,5-trihydroxy-2-methoxy-8-methylnon-6-enoyl]amino]azepan-3-yl] tetradecanoate
Synonyms:
Standard InCHIKey:	PFRKTXMXGDERHT-UCDUEDMDSA-N
Standard InCHI:	InChI=1S/C32H58N2O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-27(36)42-24-19-20-25(32(40)34(4)22-24)33-31(39)30(41-5)29(38)28(37)26(35)21-18-23(2)3/h18,21,23-26,28-30,35,37-38H,6-17,19-20,22H2,1-5H3,(H,33,39)/b21-18+/t24-,25-,26+,28-,29+,30+/m0/s1
SMILES:	CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@H](C(=O)N(C1)C)N=C([C@@H]([C@@H]([C@H]([C@@H](/C=C/C(C)C)O)O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446079
PubChem CID:	6444128
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0001189] N-acyl-alpha amino acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32703	pachastrissa sp.	Species	Calthropellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346943]
NPO32703	pachastrissa sp.	Species	Calthropellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398554]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	60
IC50	7
Others	4

Activity Type	# Activity
Cell Line	66
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	4.188	nM	PMID[514984]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	9.772	nM	PMID[514984]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	20.8	nM	PMID[514984]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	2.606	nM	PMID[514984]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	10.0	nM	PMID[514984]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	6.839	nM	PMID[514984]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	10.81	nM	PMID[514984]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	19.95	nM	PMID[514984]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	36.22	nM	PMID[514984]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	14996.85	nM	PMID[514984]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	8.11	nM	PMID[514984]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	6.427	nM	PMID[514984]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	6.427	nM	PMID[514984]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	8.091	nM	PMID[514984]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	2.864	nM	PMID[514984]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	7.816	nM	PMID[514984]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	4645.15	nM	PMID[514984]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	1.5	nM	PMID[514984]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	7.998	nM	PMID[514984]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	2.099	nM	PMID[514984]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	4.325	nM	PMID[514984]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	6.109	nM	PMID[514984]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	179.47	nM	PMID[514984]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	5.768	nM	PMID[514984]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	4.178	nM	PMID[514984]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	16.44	nM	PMID[514984]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	12.76	nM	PMID[514984]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	89.54	nM	PMID[514984]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	14996.85	nM	PMID[514984]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	14.0	nM	PMID[514984]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	2.163	nM	PMID[514984]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	33.42	nM	PMID[514984]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	5.768	nM	PMID[514984]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	1.5	nM	PMID[514984]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	1.945	nM	PMID[514984]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	104.71	nM	PMID[514984]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	2.472	nM	PMID[514984]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	27.99	nM	PMID[514984]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	3.597	nM	PMID[514984]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	1076.47	nM	PMID[514984]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	11.4	nM	PMID[514984]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	2.844	nM	PMID[514984]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	72.11	nM	PMID[514984]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	1.5	nM	PMID[514984]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	8.072	nM	PMID[514984]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	21.58	nM	PMID[514984]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2.35	nM	PMID[514984]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	6.745	nM	PMID[514984]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	1.5	nM	PMID[514984]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	33.11	nM	PMID[514984]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	4.571	nM	PMID[514984]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	172.98	nM	PMID[514984]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	12.25	nM	PMID[514984]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	7.047	nM	PMID[514984]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	5.916	nM	PMID[514984]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	11.35	nM	PMID[514984]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	4.786	nM	PMID[514984]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	2.594	nM	PMID[514984]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	61.52	nM	PMID[514984]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	133.66	nM	PMID[514984]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[514985]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2.0	nM	PMID[514985]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	500.0	nM	PMID[514985]
NPT5374	Individual Protein	Methionine aminopeptidase 1	Homo sapiens	Ratio	=	2.4	n.a.	PMID[514986]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	2.0	nM	PMID[514987]
NPT2	Others	Unspecified		IC50	=	85.0	nM	PMID[514985]
NPT2	Others	Unspecified		Ratio	=	2.1	n.a.	PMID[514986]
NPT2	Others	Unspecified		Ratio	=	2.6	n.a.	PMID[514986]
NPT35	Others	n.a.		Solubility	=	0.000002	ug.mL-1	PMID[514987]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC273185 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	100
0.1-0.2	854
0.2-0.3	9232
0.3-0.4	22567
0.4-0.5	8021
0.5-0.6	1658
0.6-0.7	258
0.7-0.8	5
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9018	High Similarity	NPC251122
0.8087	Intermediate Similarity	NPC74035
0.7642	Intermediate Similarity	NPC103391
0.7642	Intermediate Similarity	NPC472536
0.7398	Intermediate Similarity	NPC476875
0.7154	Intermediate Similarity	NPC315188
0.7107	Intermediate Similarity	NPC476877
0.7105	Intermediate Similarity	NPC39290
0.7105	Intermediate Similarity	NPC159369
0.7049	Intermediate Similarity	NPC205176
0.6992	Remote Similarity	NPC476876
0.6992	Remote Similarity	NPC475918
0.6959	Remote Similarity	NPC315809
0.6959	Remote Similarity	NPC314050
0.688	Remote Similarity	NPC171734
0.6866	Remote Similarity	NPC470650
0.6866	Remote Similarity	NPC470653
0.6866	Remote Similarity	NPC470654
0.6855	Remote Similarity	NPC201128
0.6807	Remote Similarity	NPC469739
0.6786	Remote Similarity	NPC99864
0.6746	Remote Similarity	NPC207820
0.6714	Remote Similarity	NPC120420
0.6692	Remote Similarity	NPC470652
0.6691	Remote Similarity	NPC309525
0.6691	Remote Similarity	NPC120335
0.6689	Remote Similarity	NPC135121
0.6667	Remote Similarity	NPC477217
0.6667	Remote Similarity	NPC188785
0.6667	Remote Similarity	NPC201244
0.6642	Remote Similarity	NPC160688
0.6639	Remote Similarity	NPC475758
0.6618	Remote Similarity	NPC314512
0.6618	Remote Similarity	NPC314451
0.6618	Remote Similarity	NPC313342
0.6618	Remote Similarity	NPC313333
0.6613	Remote Similarity	NPC471097
0.6613	Remote Similarity	NPC475149
0.66	Remote Similarity	NPC2501
0.6594	Remote Similarity	NPC477793
0.6594	Remote Similarity	NPC329919
0.6591	Remote Similarity	NPC6531
0.6587	Remote Similarity	NPC154601
0.6585	Remote Similarity	NPC233932
0.6585	Remote Similarity	NPC475791
0.6585	Remote Similarity	NPC13175
0.6579	Remote Similarity	NPC228638
0.6561	Remote Similarity	NPC471053
0.6561	Remote Similarity	NPC471052
0.6561	Remote Similarity	NPC471051
0.6558	Remote Similarity	NPC316244
0.6516	Remote Similarity	NPC297145
0.6516	Remote Similarity	NPC197743
0.6515	Remote Similarity	NPC296043
0.6515	Remote Similarity	NPC30196
0.6513	Remote Similarity	NPC162104
0.6507	Remote Similarity	NPC46098
0.6507	Remote Similarity	NPC163392
0.6507	Remote Similarity	NPC239762
0.6507	Remote Similarity	NPC307357
0.6507	Remote Similarity	NPC268841
0.6496	Remote Similarity	NPC36254
0.6493	Remote Similarity	NPC477237
0.6491	Remote Similarity	NPC474312
0.6486	Remote Similarity	NPC52748
0.6483	Remote Similarity	NPC127741
0.6471	Remote Similarity	NPC473341
0.6471	Remote Similarity	NPC122590
0.6466	Remote Similarity	NPC329216
0.6462	Remote Similarity	NPC29501
0.6446	Remote Similarity	NPC192066
0.6446	Remote Similarity	NPC23454
0.6446	Remote Similarity	NPC17290
0.6446	Remote Similarity	NPC70323
0.6446	Remote Similarity	NPC262312
0.6446	Remote Similarity	NPC35269
0.6446	Remote Similarity	NPC256570
0.6446	Remote Similarity	NPC3568
0.6442	Remote Similarity	NPC477462
0.6439	Remote Similarity	NPC471645
0.6424	Remote Similarity	NPC471820
0.6424	Remote Similarity	NPC471821
0.6418	Remote Similarity	NPC235625
0.6417	Remote Similarity	NPC111567
0.6417	Remote Similarity	NPC263545
0.6417	Remote Similarity	NPC282705
0.6417	Remote Similarity	NPC473581
0.6417	Remote Similarity	NPC186840
0.6417	Remote Similarity	NPC475125
0.6417	Remote Similarity	NPC473604
0.6417	Remote Similarity	NPC182632
0.6417	Remote Similarity	NPC15851
0.6417	Remote Similarity	NPC473950
0.6417	Remote Similarity	NPC309898
0.6412	Remote Similarity	NPC1111
0.6412	Remote Similarity	NPC261750
0.6406	Remote Similarity	NPC251330
0.6403	Remote Similarity	NPC314282
0.6397	Remote Similarity	NPC477238
0.6378	Remote Similarity	NPC323720
0.6376	Remote Similarity	NPC476978
0.637	Remote Similarity	NPC68865
0.6364	Remote Similarity	NPC471202
0.6364	Remote Similarity	NPC63191
0.6357	Remote Similarity	NPC470655
0.6357	Remote Similarity	NPC470651
0.6351	Remote Similarity	NPC71866
0.6351	Remote Similarity	NPC309450
0.6351	Remote Similarity	NPC475266
0.6351	Remote Similarity	NPC247776
0.6351	Remote Similarity	NPC475278
0.6351	Remote Similarity	NPC304299
0.6343	Remote Similarity	NPC475642
0.6341	Remote Similarity	NPC197294
0.6341	Remote Similarity	NPC183449
0.6341	Remote Similarity	NPC8098
0.6341	Remote Similarity	NPC45313
0.6341	Remote Similarity	NPC26108
0.6333	Remote Similarity	NPC139782
0.6333	Remote Similarity	NPC74672
0.6333	Remote Similarity	NPC242503
0.6333	Remote Similarity	NPC43074
0.6333	Remote Similarity	NPC209047
0.6328	Remote Similarity	NPC271269
0.6328	Remote Similarity	NPC473252
0.6327	Remote Similarity	NPC315848
0.6327	Remote Similarity	NPC315210
0.6319	Remote Similarity	NPC246079
0.6312	Remote Similarity	NPC313962
0.6311	Remote Similarity	NPC54961
0.6311	Remote Similarity	NPC158445
0.6311	Remote Similarity	NPC282088
0.6311	Remote Similarity	NPC156782
0.6311	Remote Similarity	NPC157353
0.6294	Remote Similarity	NPC314361
0.6288	Remote Similarity	NPC60432
0.6288	Remote Similarity	NPC314550
0.6283	Remote Similarity	NPC474833
0.6281	Remote Similarity	NPC475603
0.6281	Remote Similarity	NPC61894
0.628	Remote Similarity	NPC273755
0.625	Remote Similarity	NPC145113
0.625	Remote Similarity	NPC14537
0.6242	Remote Similarity	NPC473354
0.6242	Remote Similarity	NPC471165
0.624	Remote Similarity	NPC220234
0.6231	Remote Similarity	NPC475150
0.6231	Remote Similarity	NPC474099
0.6231	Remote Similarity	NPC70235
0.6226	Remote Similarity	NPC471527
0.6225	Remote Similarity	NPC5620
0.6224	Remote Similarity	NPC316401
0.6222	Remote Similarity	NPC201968
0.622	Remote Similarity	NPC72401
0.622	Remote Similarity	NPC325339
0.622	Remote Similarity	NPC477198
0.6218	Remote Similarity	NPC470902
0.6214	Remote Similarity	NPC474371
0.621	Remote Similarity	NPC175614
0.6205	Remote Similarity	NPC50016
0.62	Remote Similarity	NPC197682
0.62	Remote Similarity	NPC176226
0.619	Remote Similarity	NPC473224
0.6187	Remote Similarity	NPC316133
0.6187	Remote Similarity	NPC314629
0.6187	Remote Similarity	NPC318445
0.6187	Remote Similarity	NPC50520
0.6184	Remote Similarity	NPC262077
0.6182	Remote Similarity	NPC306804
0.6176	Remote Similarity	NPC471048
0.6176	Remote Similarity	NPC471049
0.6176	Remote Similarity	NPC471050
0.617	Remote Similarity	NPC473249
0.6165	Remote Similarity	NPC478024
0.6165	Remote Similarity	NPC469865
0.6164	Remote Similarity	NPC1390
0.6164	Remote Similarity	NPC62104
0.6159	Remote Similarity	NPC156379
0.6159	Remote Similarity	NPC23963
0.6159	Remote Similarity	NPC475383
0.6145	Remote Similarity	NPC159767
0.6145	Remote Similarity	NPC155506
0.6135	Remote Similarity	NPC107938
0.6135	Remote Similarity	NPC294516
0.6133	Remote Similarity	NPC168113
0.6131	Remote Similarity	NPC45037
0.6129	Remote Similarity	NPC7817
0.6129	Remote Similarity	NPC475168
0.6119	Remote Similarity	NPC469597
0.6111	Remote Similarity	NPC475440
0.6111	Remote Similarity	NPC234542
0.6103	Remote Similarity	NPC209734
0.6099	Remote Similarity	NPC315058
0.609	Remote Similarity	NPC181510
0.609	Remote Similarity	NPC47857
0.609	Remote Similarity	NPC168758
0.6087	Remote Similarity	NPC11379
0.6087	Remote Similarity	NPC230849
0.6084	Remote Similarity	NPC316205
0.6084	Remote Similarity	NPC137627

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC273185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	548
0.2-0.3	3208
0.3-0.4	4104
0.4-0.5	1023
0.5-0.6	161
0.6-0.7	16
0.7-0.8	2
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
0.7603	Intermediate Similarity	NPD6421	Discontinued
0.7068	Intermediate Similarity	NPD8273	Phase 1
0.6786	Remote Similarity	NPD8415	Approved
0.6738	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8299	Approved
0.6618	Remote Similarity	NPD8340	Approved
0.6618	Remote Similarity	NPD8341	Approved
0.6618	Remote Similarity	NPD8342	Approved
0.6541	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8392	Approved
0.65	Remote Similarity	NPD8390	Approved
0.65	Remote Similarity	NPD8391	Approved
0.6449	Remote Similarity	NPD8451	Approved
0.6449	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD8448	Approved
0.6343	Remote Similarity	NPD6935	Phase 3
0.6343	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8394	Approved
0.6296	Remote Similarity	NPD7641	Discontinued
0.6284	Remote Similarity	NPD8384	Approved
0.6187	Remote Similarity	NPD7642	Approved
0.617	Remote Similarity	NPD7747	Phase 1
0.617	Remote Similarity	NPD7746	Phase 1
0.6148	Remote Similarity	NPD7983	Approved
0.6103	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.604	Remote Similarity	NPD8173	Phase 2
0.604	Remote Similarity	NPD8172	Phase 2
0.6031	Remote Similarity	NPD8140	Approved
0.5975	Remote Similarity	NPD8414	Discontinued
0.5952	Remote Similarity	NPD4228	Discovery
0.5942	Remote Similarity	NPD6918	Phase 1
0.5929	Remote Similarity	NPD8444	Approved
0.5929	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8307	Discontinued
0.5906	Remote Similarity	NPD8038	Phase 2
0.5896	Remote Similarity	NPD6420	Discontinued
0.5887	Remote Similarity	NPD7623	Phase 3
0.5887	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD1719	Phase 1
0.5852	Remote Similarity	NPD2204	Approved
0.5845	Remote Similarity	NPD7830	Approved
0.5845	Remote Similarity	NPD7829	Approved
0.584	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5839	Remote Similarity	NPD8417	Discontinued
0.5839	Remote Similarity	NPD7916	Approved
0.5839	Remote Similarity	NPD7915	Approved
0.5833	Remote Similarity	NPD8323	Discontinued
0.5827	Remote Similarity	NPD7839	Suspended
0.5821	Remote Similarity	NPD8306	Approved
0.5821	Remote Similarity	NPD8305	Approved
0.5806	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD1407	Approved
0.5802	Remote Similarity	NPD2259	Approved
0.5802	Remote Similarity	NPD2258	Approved
0.5797	Remote Similarity	NPD869	Approved
0.5785	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD3626	Phase 3
0.5775	Remote Similarity	NPD8080	Discontinued
0.5769	Remote Similarity	NPD7651	Approved
0.5764	Remote Similarity	NPD2584	Suspended
0.5755	Remote Similarity	NPD7500	Approved
0.5735	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD3716	Discontinued
0.5725	Remote Similarity	NPD1000	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD1385	Discontinued
0.5704	Remote Similarity	NPD6413	Approved
0.5704	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5695	Remote Similarity	NPD8416	Discontinued
0.5682	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.568	Remote Similarity	NPD4261	Phase 1
0.5667	Remote Similarity	NPD882	Phase 2
0.5667	Remote Similarity	NPD883	Phase 2
0.5662	Remote Similarity	NPD8087	Discontinued
0.5656	Remote Similarity	NPD7759	Phase 2
0.5656	Remote Similarity	NPD7760	Phase 2
0.5652	Remote Similarity	NPD1376	Discontinued
0.5645	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3160	Suspended
0.5634	Remote Similarity	NPD8347	Approved
0.5634	Remote Similarity	NPD8346	Approved
0.5634	Remote Similarity	NPD8345	Approved
0.5608	Remote Similarity	NPD7751	Phase 1
0.5608	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4738	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data