NPASS Compound

Structure

CID311702 OpenBabel06191716122D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.0044 2.9274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2279 3.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6943 4.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 -2.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5374 2.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6938 2.9269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5386 3.4144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2271 1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2268 0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 -1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 1.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8492 3.4148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 2.9265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8495 4.3902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3828 1.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5368 0.4874 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9763 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6902 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6909 -0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6911 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 0.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0050 4.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5371 1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5565 -1.4755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5567 -1.4771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0199 1.9639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0053 5.8534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 4.3907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 28 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 16 2 1 6 0 0 0 16 19 1 0 0 0 0 17 3 1 1 0 0 0 17 27 1 0 0 0 0 18 4 1 1 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 29 1 6 0 0 0 20 25 1 0 0 0 0 20 29 1 6 0 0 0 21 28 1 6 0 0 0 22 30 2 0 0 0 0 23 25 1 0 0 0 0 23 31 2 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 26 2 0 0 0 0 26 28 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 5 1 6 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.29
Volume:	504.047
LogP:	4.359
LogD:	2.949
LogS:	-4.575
# Rotatable Bonds:	5
TPSA:	88.51
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	5.187
Fsp3:	0.724
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.284
MDCK Permeability:	1.8318418369744904e-05
Pgp-inhibitor:	0.774
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.278
30% Bioavailability (F30%):	0.82

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.484
Plasma Protein Binding (PPB):	93.37078094482422%
Volume Distribution (VD):	0.462
Pgp-substrate:	2.912710189819336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.362
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.257
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	9.005
Half-life (T1/2):	0.521

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.439
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.911
Maximum Recommended Daily Dose:	0.278
Skin Sensitization:	0.28
Carcinogencity:	0.367
Eye Corrosion:	0.453
Eye Irritation:	0.017
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC311702

Natural Product ID:	NPC311702
*Common Name:**	25R-Antcin B
IUPAC Name:	(2R,6R)-2-methyl-3-methylidene-6-[(4S,5S,10S,13R,14R,17R)-4,10,13-trimethyl-3,7,11-trioxo-1,2,4,5,6,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]heptanoic acid
Synonyms:
Standard InCHIKey:	DVORYMAGXQGBQK-IXXHGVNUSA-N
Standard InCHI:	InChI=1S/C29H40O5/c1-15(17(3)27(33)34)7-8-16(2)19-9-10-20-25-23(31)13-21-18(4)22(30)11-12-28(21,5)26(25)24(32)14-29(19,20)6/h16-21H,1,7-14H2,2-6H3,(H,33,34)/t16-,17-,18+,19-,20+,21+,28+,29-/m1/s1
SMILES:	C[C@H](C(=C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC(=O)C1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)[C@H]2C)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105009
PubChem CID:	68150386
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
NPO15630	Manduca sexta	Species	Sphingidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8748375]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6926	Colubrina asiatica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11787	Orthosiphon wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6926	Colubrina asiatica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27240	Alcyonium grandis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11787	Orthosiphon wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29200	Moquiniastrum paniculatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4909	Hilliardiella oligocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15630	Manduca sexta	Species	Sphingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6533	Dipterocarpus pilosus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17660	Podocarpus lawrencei	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25603	Lycoris x chejuensis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6926	Colubrina asiatica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11557	Echinus miliaris	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	41400.0	nM	PMID[485840]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	33400.0	nM	PMID[485840]

☑ 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 NPC311702 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	147
0.1-0.2	1137
0.2-0.3	6484
0.3-0.4	15033
0.4-0.5	7822
0.5-0.6	6934
0.6-0.7	3966
0.7-0.8	980
0.8-0.85	140
0.85-0.9	40
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC123319
1.0	High Similarity	NPC94531
0.9747	High Similarity	NPC168188
0.9747	High Similarity	NPC470015
0.9383	High Similarity	NPC320801
0.9383	High Similarity	NPC209882
0.9268	High Similarity	NPC473038
0.9268	High Similarity	NPC11711
0.9136	High Similarity	NPC260956
0.9136	High Similarity	NPC320514
0.9136	High Similarity	NPC321289
0.9136	High Similarity	NPC327969
0.9012	High Similarity	NPC477372
0.9012	High Similarity	NPC38350
0.9012	High Similarity	NPC201912
0.8824	High Similarity	NPC136948
0.881	High Similarity	NPC29447
0.881	High Similarity	NPC8571
0.8795	High Similarity	NPC469561
0.8795	High Similarity	NPC69279
0.8795	High Similarity	NPC83569
0.8795	High Similarity	NPC271784
0.878	High Similarity	NPC147066
0.8778	High Similarity	NPC43747
0.8765	High Similarity	NPC477371
0.8675	High Similarity	NPC133391
0.8667	High Similarity	NPC472941
0.8667	High Similarity	NPC456
0.8659	High Similarity	NPC26139
0.8652	High Similarity	NPC166906
0.8636	High Similarity	NPC204341
0.8625	High Similarity	NPC180886
0.8621	High Similarity	NPC262043
0.8588	High Similarity	NPC142649
0.8571	High Similarity	NPC477373
0.8556	High Similarity	NPC317586
0.8556	High Similarity	NPC173875
0.8556	High Similarity	NPC174948
0.8556	High Similarity	NPC469995
0.8556	High Similarity	NPC470016
0.8556	High Similarity	NPC318282
0.8556	High Similarity	NPC241156
0.8554	High Similarity	NPC278459
0.8506	High Similarity	NPC242864
0.8488	Intermediate Similarity	NPC222613
0.8488	Intermediate Similarity	NPC475022
0.8488	Intermediate Similarity	NPC118648
0.8471	Intermediate Similarity	NPC473246
0.8471	Intermediate Similarity	NPC164577
0.8462	Intermediate Similarity	NPC328371
0.8462	Intermediate Similarity	NPC96859
0.8462	Intermediate Similarity	NPC328162
0.8462	Intermediate Similarity	NPC305483
0.8462	Intermediate Similarity	NPC125622
0.8452	Intermediate Similarity	NPC3511
0.8452	Intermediate Similarity	NPC142253
0.8415	Intermediate Similarity	NPC469996
0.8415	Intermediate Similarity	NPC74410
0.8409	Intermediate Similarity	NPC214387
0.8409	Intermediate Similarity	NPC54689
0.8391	Intermediate Similarity	NPC96496
0.8391	Intermediate Similarity	NPC99909
0.8387	Intermediate Similarity	NPC51370
0.8387	Intermediate Similarity	NPC287833
0.8372	Intermediate Similarity	NPC469948
0.837	Intermediate Similarity	NPC320306
0.8354	Intermediate Similarity	NPC223187
0.8353	Intermediate Similarity	NPC97913
0.8352	Intermediate Similarity	NPC171395
0.8352	Intermediate Similarity	NPC255809
0.8352	Intermediate Similarity	NPC37646
0.8333	Intermediate Similarity	NPC25750
0.8333	Intermediate Similarity	NPC206810
0.8333	Intermediate Similarity	NPC471898
0.8315	Intermediate Similarity	NPC477149
0.8315	Intermediate Similarity	NPC477147
0.8313	Intermediate Similarity	NPC274996
0.8313	Intermediate Similarity	NPC196827
0.8313	Intermediate Similarity	NPC472490
0.8295	Intermediate Similarity	NPC471722
0.8293	Intermediate Similarity	NPC165711
0.828	Intermediate Similarity	NPC197386
0.828	Intermediate Similarity	NPC235464
0.828	Intermediate Similarity	NPC166745
0.8276	Intermediate Similarity	NPC31564
0.8276	Intermediate Similarity	NPC145879
0.8276	Intermediate Similarity	NPC6247
0.8276	Intermediate Similarity	NPC72133
0.8276	Intermediate Similarity	NPC155011
0.8276	Intermediate Similarity	NPC474732
0.8276	Intermediate Similarity	NPC474733
0.8276	Intermediate Similarity	NPC474778
0.8276	Intermediate Similarity	NPC28252
0.8276	Intermediate Similarity	NPC55309
0.8261	Intermediate Similarity	NPC40765
0.8261	Intermediate Similarity	NPC3772
0.8261	Intermediate Similarity	NPC243525
0.8256	Intermediate Similarity	NPC87552
0.8256	Intermediate Similarity	NPC214043
0.8256	Intermediate Similarity	NPC472865
0.8256	Intermediate Similarity	NPC85774
0.8256	Intermediate Similarity	NPC96095
0.8235	Intermediate Similarity	NPC302661
0.8235	Intermediate Similarity	NPC238991
0.8235	Intermediate Similarity	NPC472239
0.8235	Intermediate Similarity	NPC193347
0.8222	Intermediate Similarity	NPC26888
0.8211	Intermediate Similarity	NPC293753
0.8211	Intermediate Similarity	NPC234892
0.8202	Intermediate Similarity	NPC474570
0.8202	Intermediate Similarity	NPC31985
0.8202	Intermediate Similarity	NPC1015
0.8202	Intermediate Similarity	NPC474889
0.8202	Intermediate Similarity	NPC473039
0.8191	Intermediate Similarity	NPC316964
0.8191	Intermediate Similarity	NPC88198
0.8191	Intermediate Similarity	NPC157787
0.8191	Intermediate Similarity	NPC327431
0.8182	Intermediate Similarity	NPC475740
0.8182	Intermediate Similarity	NPC476409
0.8182	Intermediate Similarity	NPC159046
0.8182	Intermediate Similarity	NPC233836
0.8182	Intermediate Similarity	NPC187376
0.8182	Intermediate Similarity	NPC58063
0.8172	Intermediate Similarity	NPC122294
0.8172	Intermediate Similarity	NPC108078
0.8172	Intermediate Similarity	NPC121339
0.8172	Intermediate Similarity	NPC106557
0.8171	Intermediate Similarity	NPC246445
0.8161	Intermediate Similarity	NPC472940
0.8161	Intermediate Similarity	NPC472931
0.8161	Intermediate Similarity	NPC269638
0.8161	Intermediate Similarity	NPC474537
0.814	Intermediate Similarity	NPC477852
0.814	Intermediate Similarity	NPC102197
0.814	Intermediate Similarity	NPC41539
0.814	Intermediate Similarity	NPC310470
0.814	Intermediate Similarity	NPC105803
0.814	Intermediate Similarity	NPC167103
0.814	Intermediate Similarity	NPC49019
0.8132	Intermediate Similarity	NPC66429
0.8132	Intermediate Similarity	NPC243866
0.8132	Intermediate Similarity	NPC152897
0.8125	Intermediate Similarity	NPC160817
0.8118	Intermediate Similarity	NPC55869
0.8118	Intermediate Similarity	NPC189237
0.8111	Intermediate Similarity	NPC469400
0.8111	Intermediate Similarity	NPC148414
0.8111	Intermediate Similarity	NPC175628
0.8111	Intermediate Similarity	NPC111585
0.8105	Intermediate Similarity	NPC124211
0.8105	Intermediate Similarity	NPC302537
0.8105	Intermediate Similarity	NPC163372
0.8105	Intermediate Similarity	NPC99411
0.8095	Intermediate Similarity	NPC215843
0.8095	Intermediate Similarity	NPC192744
0.8095	Intermediate Similarity	NPC192329
0.8095	Intermediate Similarity	NPC158846
0.8095	Intermediate Similarity	NPC199595
0.809	Intermediate Similarity	NPC117122
0.809	Intermediate Similarity	NPC131470
0.809	Intermediate Similarity	NPC143767
0.8085	Intermediate Similarity	NPC16021
0.8085	Intermediate Similarity	NPC471717
0.8072	Intermediate Similarity	NPC66105
0.8072	Intermediate Similarity	NPC212661
0.8072	Intermediate Similarity	NPC471035
0.8068	Intermediate Similarity	NPC186975
0.8068	Intermediate Similarity	NPC472869
0.8068	Intermediate Similarity	NPC212843
0.8065	Intermediate Similarity	NPC42042
0.8065	Intermediate Similarity	NPC95565
0.8046	Intermediate Similarity	NPC144258
0.8046	Intermediate Similarity	NPC237712
0.8046	Intermediate Similarity	NPC19849
0.8046	Intermediate Similarity	NPC165064
0.8046	Intermediate Similarity	NPC59453
0.8046	Intermediate Similarity	NPC221758
0.8046	Intermediate Similarity	NPC472864
0.8043	Intermediate Similarity	NPC184870
0.8025	Intermediate Similarity	NPC321017
0.8023	Intermediate Similarity	NPC69101
0.8023	Intermediate Similarity	NPC296367
0.8023	Intermediate Similarity	NPC472867
0.8023	Intermediate Similarity	NPC100297
0.8023	Intermediate Similarity	NPC251779
0.8023	Intermediate Similarity	NPC469325
0.8023	Intermediate Similarity	NPC240302
0.8022	Intermediate Similarity	NPC154101
0.8022	Intermediate Similarity	NPC230064
0.8022	Intermediate Similarity	NPC23434
0.8022	Intermediate Similarity	NPC297265
0.8021	Intermediate Similarity	NPC204450
0.8021	Intermediate Similarity	NPC308726
0.8021	Intermediate Similarity	NPC119601
0.8021	Intermediate Similarity	NPC195290
0.8021	Intermediate Similarity	NPC53222
0.8	Intermediate Similarity	NPC474704
0.8	Intermediate Similarity	NPC84271
0.8	Intermediate Similarity	NPC86319

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 NPC311702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1549
0.2-0.3	4204
0.3-0.4	2251
0.4-0.5	542
0.5-0.6	192
0.6-0.7	178
0.7-0.8	85
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8427	Intermediate Similarity	NPD5281	Approved
0.8427	Intermediate Similarity	NPD5284	Approved
0.8235	Intermediate Similarity	NPD4223	Phase 3
0.8235	Intermediate Similarity	NPD4221	Approved
0.8161	Intermediate Similarity	NPD5329	Approved
0.8152	Intermediate Similarity	NPD5695	Phase 3
0.8132	Intermediate Similarity	NPD6399	Phase 3
0.809	Intermediate Similarity	NPD6672	Approved
0.809	Intermediate Similarity	NPD5737	Approved
0.8085	Intermediate Similarity	NPD5696	Approved
0.8068	Intermediate Similarity	NPD5280	Approved
0.8068	Intermediate Similarity	NPD5690	Phase 2
0.8068	Intermediate Similarity	NPD4694	Approved
0.8046	Intermediate Similarity	NPD4197	Approved
0.8046	Intermediate Similarity	NPD4786	Approved
0.8022	Intermediate Similarity	NPD6050	Approved
0.8	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6904	Approved
0.8	Intermediate Similarity	NPD6673	Approved
0.8	Intermediate Similarity	NPD6080	Approved
0.7979	Intermediate Similarity	NPD6083	Phase 2
0.7979	Intermediate Similarity	NPD6084	Phase 2
0.7976	Intermediate Similarity	NPD3617	Approved
0.7927	Intermediate Similarity	NPD5733	Approved
0.7912	Intermediate Similarity	NPD5692	Phase 3
0.7865	Intermediate Similarity	NPD5205	Approved
0.7865	Intermediate Similarity	NPD6409	Approved
0.7865	Intermediate Similarity	NPD4138	Approved
0.7865	Intermediate Similarity	NPD5330	Approved
0.7865	Intermediate Similarity	NPD4689	Approved
0.7865	Intermediate Similarity	NPD4688	Approved
0.7865	Intermediate Similarity	NPD7146	Approved
0.7865	Intermediate Similarity	NPD6684	Approved
0.7865	Intermediate Similarity	NPD4693	Phase 3
0.7865	Intermediate Similarity	NPD5279	Phase 3
0.7865	Intermediate Similarity	NPD7521	Approved
0.7865	Intermediate Similarity	NPD7334	Approved
0.7865	Intermediate Similarity	NPD4690	Approved
0.7841	Intermediate Similarity	NPD3665	Phase 1
0.7841	Intermediate Similarity	NPD3133	Approved
0.7841	Intermediate Similarity	NPD3666	Approved
0.7826	Intermediate Similarity	NPD5694	Approved
0.7816	Intermediate Similarity	NPD3667	Approved
0.7802	Intermediate Similarity	NPD5328	Approved
0.7802	Intermediate Similarity	NPD4753	Phase 2
0.7791	Intermediate Similarity	NPD4695	Discontinued
0.7778	Intermediate Similarity	NPD4747	Approved
0.7766	Intermediate Similarity	NPD5210	Approved
0.7766	Intermediate Similarity	NPD4629	Approved
0.7717	Intermediate Similarity	NPD5207	Approved
0.7711	Intermediate Similarity	NPD4687	Approved
0.7701	Intermediate Similarity	NPD4692	Approved
0.7701	Intermediate Similarity	NPD4139	Approved
0.7692	Intermediate Similarity	NPD5208	Approved
0.7692	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6903	Approved
0.7684	Intermediate Similarity	NPD7614	Phase 1
0.7683	Intermediate Similarity	NPD6081	Approved
0.7683	Intermediate Similarity	NPD5276	Approved
0.7667	Intermediate Similarity	NPD3618	Phase 1
0.7667	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6098	Approved
0.7654	Intermediate Similarity	NPD4137	Phase 3
0.7634	Intermediate Similarity	NPD6079	Approved
0.7634	Intermediate Similarity	NPD5693	Phase 1
0.7634	Intermediate Similarity	NPD7515	Phase 2
0.7579	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4691	Approved
0.7527	Intermediate Similarity	NPD4096	Approved
0.75	Intermediate Similarity	NPD4518	Approved
0.7474	Intermediate Similarity	NPD7748	Approved
0.7471	Intermediate Similarity	NPD4195	Approved
0.7449	Intermediate Similarity	NPD6404	Discontinued
0.7444	Intermediate Similarity	NPD3668	Phase 3
0.7426	Intermediate Similarity	NPD6675	Approved
0.7426	Intermediate Similarity	NPD7128	Approved
0.7426	Intermediate Similarity	NPD6402	Approved
0.7426	Intermediate Similarity	NPD5739	Approved
0.7396	Intermediate Similarity	NPD5654	Approved
0.7368	Intermediate Similarity	NPD4202	Approved
0.7368	Intermediate Similarity	NPD5133	Approved
0.7363	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4788	Approved
0.732	Intermediate Similarity	NPD5221	Approved
0.732	Intermediate Similarity	NPD4697	Phase 3
0.732	Intermediate Similarity	NPD5222	Approved
0.732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5091	Approved
0.7294	Intermediate Similarity	NPD4058	Approved
0.7292	Intermediate Similarity	NPD6001	Approved
0.7283	Intermediate Similarity	NPD4623	Approved
0.7283	Intermediate Similarity	NPD4519	Discontinued
0.7282	Intermediate Similarity	NPD7320	Approved
0.7282	Intermediate Similarity	NPD6899	Approved
0.7282	Intermediate Similarity	NPD6881	Approved
0.7245	Intermediate Similarity	NPD5959	Approved
0.7245	Intermediate Similarity	NPD5173	Approved
0.7245	Intermediate Similarity	NPD7902	Approved
0.7245	Intermediate Similarity	NPD4755	Approved
0.7212	Intermediate Similarity	NPD6372	Approved
0.7212	Intermediate Similarity	NPD6373	Approved
0.7184	Intermediate Similarity	NPD6614	Approved
0.7184	Intermediate Similarity	NPD5697	Approved
0.7184	Intermediate Similarity	NPD5701	Approved
0.7159	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD6883	Approved
0.7143	Intermediate Similarity	NPD7732	Phase 3
0.7143	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD6011	Approved
0.7108	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5286	Approved
0.71	Intermediate Similarity	NPD4700	Approved
0.71	Intermediate Similarity	NPD4696	Approved
0.71	Intermediate Similarity	NPD5285	Approved
0.7093	Intermediate Similarity	NPD4785	Approved
0.7093	Intermediate Similarity	NPD4784	Approved
0.7083	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD8034	Phase 2
0.7075	Intermediate Similarity	NPD6649	Approved
0.7075	Intermediate Similarity	NPD8130	Phase 1
0.7075	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6617	Approved
0.7075	Intermediate Similarity	NPD6869	Approved
0.7075	Intermediate Similarity	NPD6650	Approved
0.7075	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD4224	Phase 2
0.7059	Intermediate Similarity	NPD6052	Approved
0.7059	Intermediate Similarity	NPD4243	Approved
0.7048	Intermediate Similarity	NPD6013	Approved
0.7048	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD6012	Approved
0.703	Intermediate Similarity	NPD5223	Approved
0.7021	Intermediate Similarity	NPD3573	Approved
0.7011	Intermediate Similarity	NPD7339	Approved
0.7011	Intermediate Similarity	NPD6942	Approved
0.7009	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD7638	Approved
0.6961	Remote Similarity	NPD5211	Phase 2
0.6961	Remote Similarity	NPD5224	Approved
0.6961	Remote Similarity	NPD5226	Approved
0.6961	Remote Similarity	NPD4633	Approved
0.6961	Remote Similarity	NPD5225	Approved
0.6939	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7900	Approved
0.6931	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD6008	Approved
0.6909	Remote Similarity	NPD7115	Discovery
0.6907	Remote Similarity	NPD6411	Approved
0.6893	Remote Similarity	NPD5174	Approved
0.6893	Remote Similarity	NPD4754	Approved
0.6893	Remote Similarity	NPD5175	Approved
0.6867	Remote Similarity	NPD7331	Phase 2
0.6857	Remote Similarity	NPD6412	Phase 2
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5141	Approved
0.6818	Remote Similarity	NPD6868	Approved
0.6809	Remote Similarity	NPD5363	Approved
0.6804	Remote Similarity	NPD5785	Approved
0.6789	Remote Similarity	NPD4632	Approved
0.6774	Remote Similarity	NPD5362	Discontinued
0.6774	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4767	Approved
0.6762	Remote Similarity	NPD4768	Approved
0.6747	Remote Similarity	NPD7341	Phase 2
0.6742	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6117	Approved
0.6739	Remote Similarity	NPD5369	Approved
0.6706	Remote Similarity	NPD5360	Phase 3
0.6706	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6696	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6637	Remote Similarity	NPD7101	Approved
0.6637	Remote Similarity	NPD7100	Approved
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.663	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7525	Registered
0.663	Remote Similarity	NPD5368	Approved
0.6629	Remote Similarity	NPD5275	Approved
0.6629	Remote Similarity	NPD4190	Phase 3
0.6607	Remote Similarity	NPD6009	Approved
0.6607	Remote Similarity	NPD6317	Approved
0.6593	Remote Similarity	NPD6118	Approved
0.6593	Remote Similarity	NPD6114	Approved
0.6593	Remote Similarity	NPD6697	Approved
0.6593	Remote Similarity	NPD6115	Approved
0.6566	Remote Similarity	NPD7637	Suspended
0.6552	Remote Similarity	NPD4789	Approved
0.6549	Remote Similarity	NPD6313	Approved

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