NPASS Compound

Structure

CID305483 OpenBabel06191716112D 35 38 0 0 1 0 0 0 0 0999 V2000 0.8437 -4.3895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6903 -1.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6884 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3817 3.9402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5367 0.4521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0009 -2.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0009 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6899 0.9758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2267 1.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3817 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6912 2.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8437 -3.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 -1.4635 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6884 -2.9266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3817 2.9284 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8456 -0.4882 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9757 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5367 2.4402 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2267 2.4402 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8456 2.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 1.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6911 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6911 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 -0.4882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5331 -3.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5367 1.4639 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0928 2.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0204 2.9403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5571 -0.5001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8455 -1.4882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3777 -2.9266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5330 -4.3896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 2 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 28 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 15 2 1 1 0 0 0 15 18 1 0 0 0 0 16 3 1 1 0 0 0 16 27 1 0 0 0 0 17 4 1 6 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 29 1 1 0 0 0 19 23 1 0 0 0 0 19 29 1 1 0 0 0 20 28 1 1 0 0 0 21 30 1 6 0 0 0 22 23 1 0 0 0 0 22 31 2 0 0 0 0 23 24 2 0 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 26 1 0 0 0 0 25 32 2 0 0 0 0 26 29 1 6 0 0 0 26 33 1 0 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 28 5 1 1 0 0 0 29 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	515.473
LogP:	3.745
LogD:	2.604
LogS:	-4.122
# Rotatable Bonds:	5
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	5.282
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.223
MDCK Permeability:	6.27943009021692e-05
Pgp-inhibitor:	0.761
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.044
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.732
Plasma Protein Binding (PPB):	94.79915618896484%
Volume Distribution (VD):	0.51
Pgp-substrate:	4.984978675842285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.532
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.445
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	6.995
Half-life (T1/2):	0.518

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.594
Drug-inuced Liver Injury (DILI):	0.268
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.123
Carcinogencity:	0.246
Eye Corrosion:	0.007
Eye Irritation:	0.018
Respiratory Toxicity:	0.704

Download Data

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

Natural Product: NPC305483

Natural Product ID:	NPC305483
*Common Name:**	25R-Antcin H
IUPAC Name:	(2R,6R)-6-[(3R,4S,5S,10S,12R,13R,14R,17R)-3,12-dihydroxy-4,10,13-trimethyl-7,11-dioxo-2,3,4,5,6,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoic acid
Synonyms:
Standard InCHIKey:	LVFHKUZOQUATIE-AJVWHGDVSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-14(16(3)27(34)35)7-8-15(2)18-9-10-19-23-22(31)13-20-17(4)21(30)11-12-28(20,5)24(23)25(32)26(33)29(18,19)6/h15-21,26,30,33H,1,7-13H2,2-6H3,(H,34,35)/t15-,16-,17+,18-,19+,20+,21-,26+,28+,29-/m1/s1
SMILES:	C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=C(C(=O)[C@@H]([C@]12C)O)[C@@]1(C)CC[C@H]([C@@H](C)[C@@H]1CC3=O)O)[C@@H](C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105007
PubChem CID:	68150383
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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]
NPO4176	Mosla scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15630	Manduca sexta	Species	Sphingidae	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]
NPO11787	Orthosiphon wulfenioides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27240	Alcyonium grandis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4909	Hilliardiella oligocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29200	Moquiniastrum paniculatum	Species	Asteraceae	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	5
Others	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	22000.0	nM	PMID[470524]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	23700.0	nM	PMID[470524]
NPT380	Cell Line	U-251	Homo sapiens	IC50	>	100000.0	nM	PMID[470525]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[470525]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	100000.0	nM	PMID[470525]
NPT737	Cell Line	HUVEC	Homo sapiens	Activity	=	70.5	%	PMID[470525]

☑ 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 NPC305483 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	178
0.1-0.2	1224
0.2-0.3	5082
0.3-0.4	12083
0.4-0.5	9872
0.5-0.6	6517
0.6-0.7	5264
0.7-0.8	2079
0.8-0.85	266
0.85-0.9	97
0.9-0.95	28
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96859
1.0	High Similarity	NPC328162
0.9775	High Similarity	NPC166906
0.967	High Similarity	NPC43747
0.9667	High Similarity	NPC317586
0.9667	High Similarity	NPC470016
0.9362	High Similarity	NPC163372
0.9362	High Similarity	NPC302537
0.9263	High Similarity	NPC308726
0.9263	High Similarity	NPC119601
0.9255	High Similarity	NPC316964
0.9255	High Similarity	NPC88198
0.9255	High Similarity	NPC327431
0.9255	High Similarity	NPC157787
0.9239	High Similarity	NPC173875
0.9239	High Similarity	NPC469995
0.9239	High Similarity	NPC318282
0.9239	High Similarity	NPC174948
0.9213	High Similarity	NPC143767
0.9213	High Similarity	NPC242864
0.9213	High Similarity	NPC131470
0.914	High Similarity	NPC95565
0.914	High Similarity	NPC328371
0.9121	High Similarity	NPC168027
0.9121	High Similarity	NPC185936
0.9111	High Similarity	NPC86319
0.9111	High Similarity	NPC275740
0.9082	High Similarity	NPC472925
0.9043	High Similarity	NPC320306
0.9032	High Similarity	NPC48330
0.9032	High Similarity	NPC255809
0.9011	High Similarity	NPC183283
0.9	High Similarity	NPC471722
0.899	High Similarity	NPC295244
0.8989	High Similarity	NPC72133
0.8989	High Similarity	NPC28252
0.8989	High Similarity	NPC55309
0.8969	High Similarity	NPC33973
0.8969	High Similarity	NPC251017
0.8969	High Similarity	NPC70967
0.8947	High Similarity	NPC114274
0.8936	High Similarity	NPC173272
0.8925	High Similarity	NPC245972
0.8925	High Similarity	NPC196485
0.8913	High Similarity	NPC63748
0.8889	High Similarity	NPC159046
0.8889	High Similarity	NPC233836
0.8889	High Similarity	NPC187376
0.8878	High Similarity	NPC135854
0.8878	High Similarity	NPC216245
0.8878	High Similarity	NPC470251
0.8878	High Similarity	NPC2436
0.8842	High Similarity	NPC108078
0.8817	High Similarity	NPC69454
0.8817	High Similarity	NPC25750
0.8817	High Similarity	NPC206810
0.8804	High Similarity	NPC469400
0.8791	High Similarity	NPC328539
0.8788	High Similarity	NPC51452
0.8788	High Similarity	NPC323834
0.8763	High Similarity	NPC124211
0.875	High Similarity	NPC197386
0.875	High Similarity	NPC471717
0.8737	High Similarity	NPC192428
0.8737	High Similarity	NPC249954
0.8725	High Similarity	NPC472928
0.8723	High Similarity	NPC184870
0.871	High Similarity	NPC26888
0.871	High Similarity	NPC23434
0.871	High Similarity	NPC99380
0.871	High Similarity	NPC297265
0.8696	High Similarity	NPC31985
0.8696	High Similarity	NPC1015
0.8696	High Similarity	NPC214387
0.8696	High Similarity	NPC474245
0.8696	High Similarity	NPC474704
0.8696	High Similarity	NPC475921
0.8696	High Similarity	NPC474889
0.8696	High Similarity	NPC77168
0.8696	High Similarity	NPC84271
0.8696	High Similarity	NPC102414
0.8681	High Similarity	NPC474684
0.8681	High Similarity	NPC475740
0.8681	High Similarity	NPC142361
0.8673	High Similarity	NPC195290
0.8673	High Similarity	NPC204450
0.8673	High Similarity	NPC53222
0.866	High Similarity	NPC51370
0.866	High Similarity	NPC287833
0.8652	High Similarity	NPC470015
0.8652	High Similarity	NPC168188
0.8646	High Similarity	NPC18509
0.8646	High Similarity	NPC18319
0.8632	High Similarity	NPC200702
0.8632	High Similarity	NPC259286
0.8632	High Similarity	NPC241156
0.8632	High Similarity	NPC37646
0.8617	High Similarity	NPC472930
0.8617	High Similarity	NPC12722
0.8617	High Similarity	NPC477436
0.8617	High Similarity	NPC477435
0.8602	High Similarity	NPC111585
0.8602	High Similarity	NPC477147
0.8602	High Similarity	NPC20388
0.8602	High Similarity	NPC148414
0.8602	High Similarity	NPC477149
0.8602	High Similarity	NPC175628
0.8602	High Similarity	NPC191684
0.8587	High Similarity	NPC471724
0.8586	High Similarity	NPC55872
0.8586	High Similarity	NPC236390
0.8571	High Similarity	NPC118648
0.8571	High Similarity	NPC51014
0.8571	High Similarity	NPC474732
0.8571	High Similarity	NPC145879
0.8571	High Similarity	NPC475022
0.8571	High Similarity	NPC31564
0.8571	High Similarity	NPC222613
0.8571	High Similarity	NPC474733
0.8571	High Similarity	NPC474778
0.8571	High Similarity	NPC155011
0.8571	High Similarity	NPC472924
0.8558	High Similarity	NPC472926
0.8557	High Similarity	NPC10364
0.8556	High Similarity	NPC473246
0.8542	High Similarity	NPC3772
0.8542	High Similarity	NPC40765
0.8542	High Similarity	NPC472941
0.8542	High Similarity	NPC456
0.8542	High Similarity	NPC120708
0.8542	High Similarity	NPC7124
0.8542	High Similarity	NPC125622
0.8542	High Similarity	NPC243525
0.8529	High Similarity	NPC286174
0.8529	High Similarity	NPC77947
0.8526	High Similarity	NPC469406
0.8515	High Similarity	NPC44063
0.8515	High Similarity	NPC475294
0.8511	High Similarity	NPC107690
0.8511	High Similarity	NPC233116
0.8511	High Similarity	NPC189520
0.8511	High Similarity	NPC86266
0.8511	High Similarity	NPC212301
0.8511	High Similarity	NPC110657
0.85	High Similarity	NPC96268
0.85	High Similarity	NPC28656
0.85	High Similarity	NPC235889
0.8495	Intermediate Similarity	NPC54689
0.8495	Intermediate Similarity	NPC186688
0.8485	Intermediate Similarity	NPC293753
0.8485	Intermediate Similarity	NPC473424
0.8485	Intermediate Similarity	NPC234892
0.8485	Intermediate Similarity	NPC136289
0.8478	Intermediate Similarity	NPC58063
0.8469	Intermediate Similarity	NPC476274
0.8469	Intermediate Similarity	NPC15390
0.8469	Intermediate Similarity	NPC472972
0.8469	Intermediate Similarity	NPC144956
0.8469	Intermediate Similarity	NPC205899
0.8462	Intermediate Similarity	NPC469948
0.8462	Intermediate Similarity	NPC94531
0.8462	Intermediate Similarity	NPC311702
0.8462	Intermediate Similarity	NPC197823
0.8462	Intermediate Similarity	NPC470574
0.8462	Intermediate Similarity	NPC71348
0.8462	Intermediate Similarity	NPC123319
0.8454	Intermediate Similarity	NPC121339
0.8454	Intermediate Similarity	NPC106557
0.8454	Intermediate Similarity	NPC122294
0.8454	Intermediate Similarity	NPC216904
0.8447	Intermediate Similarity	NPC272898
0.8447	Intermediate Similarity	NPC197428
0.8447	Intermediate Similarity	NPC129689
0.8447	Intermediate Similarity	NPC473036
0.8444	Intermediate Similarity	NPC278648
0.8444	Intermediate Similarity	NPC476082
0.8438	Intermediate Similarity	NPC45324
0.8438	Intermediate Similarity	NPC162001
0.8438	Intermediate Similarity	NPC477437
0.8438	Intermediate Similarity	NPC477438
0.8438	Intermediate Similarity	NPC184848
0.8438	Intermediate Similarity	NPC139570
0.8438	Intermediate Similarity	NPC222845
0.8438	Intermediate Similarity	NPC69548
0.8438	Intermediate Similarity	NPC473170
0.8438	Intermediate Similarity	NPC469599
0.8438	Intermediate Similarity	NPC472932
0.8431	Intermediate Similarity	NPC94529
0.8421	Intermediate Similarity	NPC470375
0.8421	Intermediate Similarity	NPC470254
0.8421	Intermediate Similarity	NPC475255
0.8421	Intermediate Similarity	NPC109414
0.8421	Intermediate Similarity	NPC170220
0.8421	Intermediate Similarity	NPC470376
0.8421	Intermediate Similarity	NPC141497
0.8421	Intermediate Similarity	NPC477855
0.8421	Intermediate Similarity	NPC107674
0.8416	Intermediate Similarity	NPC181265
0.8404	Intermediate Similarity	NPC289213
0.8404	Intermediate Similarity	NPC48010

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 NPC305483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1606
0.2-0.3	3957
0.3-0.4	2318
0.4-0.5	639
0.5-0.6	172
0.6-0.7	134
0.7-0.8	118
0.8-0.85	43
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8901	High Similarity	NPD5328	Approved
0.8788	High Similarity	NPD5739	Approved
0.8788	High Similarity	NPD7128	Approved
0.8788	High Similarity	NPD6675	Approved
0.8788	High Similarity	NPD6402	Approved
0.8737	High Similarity	NPD5222	Approved
0.8737	High Similarity	NPD5221	Approved
0.8737	High Similarity	NPD4697	Phase 3
0.8737	High Similarity	NPD5220	Clinical (unspecified phase)
0.871	High Similarity	NPD6079	Approved
0.8646	High Similarity	NPD5173	Approved
0.8646	High Similarity	NPD4755	Approved
0.8614	High Similarity	NPD6881	Approved
0.8614	High Similarity	NPD6899	Approved
0.8614	High Similarity	NPD7320	Approved
0.8529	High Similarity	NPD6373	Approved
0.8529	High Similarity	NPD6372	Approved
0.8515	High Similarity	NPD5697	Approved
0.8515	High Similarity	NPD5701	Approved
0.8469	Intermediate Similarity	NPD5286	Approved
0.8469	Intermediate Similarity	NPD4700	Approved
0.8469	Intermediate Similarity	NPD4696	Approved
0.8469	Intermediate Similarity	NPD5285	Approved
0.8447	Intermediate Similarity	NPD6883	Approved
0.8447	Intermediate Similarity	NPD7102	Approved
0.8447	Intermediate Similarity	NPD7290	Approved
0.8431	Intermediate Similarity	NPD6011	Approved
0.8384	Intermediate Similarity	NPD5223	Approved
0.837	Intermediate Similarity	NPD5279	Phase 3
0.837	Intermediate Similarity	NPD3618	Phase 1
0.8365	Intermediate Similarity	NPD6650	Approved
0.8365	Intermediate Similarity	NPD8130	Phase 1
0.8365	Intermediate Similarity	NPD6869	Approved
0.8365	Intermediate Similarity	NPD6649	Approved
0.8365	Intermediate Similarity	NPD6847	Approved
0.8365	Intermediate Similarity	NPD6617	Approved
0.8365	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD4786	Approved
0.835	Intermediate Similarity	NPD6012	Approved
0.835	Intermediate Similarity	NPD6013	Approved
0.835	Intermediate Similarity	NPD6014	Approved
0.8316	Intermediate Similarity	NPD7515	Phase 2
0.83	Intermediate Similarity	NPD4633	Approved
0.83	Intermediate Similarity	NPD5225	Approved
0.83	Intermediate Similarity	NPD5224	Approved
0.83	Intermediate Similarity	NPD5226	Approved
0.83	Intermediate Similarity	NPD5211	Phase 2
0.8286	Intermediate Similarity	NPD8297	Approved
0.8286	Intermediate Similarity	NPD6882	Approved
0.8265	Intermediate Similarity	NPD6083	Phase 2
0.8265	Intermediate Similarity	NPD6084	Phase 2
0.8247	Intermediate Similarity	NPD5695	Phase 3
0.8229	Intermediate Similarity	NPD6399	Phase 3
0.8218	Intermediate Similarity	NPD5174	Approved
0.8218	Intermediate Similarity	NPD5175	Approved
0.8218	Intermediate Similarity	NPD4754	Approved
0.8191	Intermediate Similarity	NPD6672	Approved
0.8191	Intermediate Similarity	NPD5737	Approved
0.8137	Intermediate Similarity	NPD5141	Approved
0.8132	Intermediate Similarity	NPD3667	Approved
0.8105	Intermediate Similarity	NPD4753	Phase 2
0.8065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD4768	Approved
0.8058	Intermediate Similarity	NPD4767	Approved
0.8056	Intermediate Similarity	NPD6868	Approved
0.8041	Intermediate Similarity	NPD4202	Approved
0.8037	Intermediate Similarity	NPD4632	Approved
0.7959	Intermediate Similarity	NPD7748	Approved
0.7957	Intermediate Similarity	NPD3665	Phase 1
0.7957	Intermediate Similarity	NPD3666	Approved
0.7957	Intermediate Similarity	NPD3133	Approved
0.7909	Intermediate Similarity	NPD6335	Approved
0.7905	Intermediate Similarity	NPD4729	Approved
0.7905	Intermediate Similarity	NPD5128	Approved
0.7905	Intermediate Similarity	NPD5168	Approved
0.7905	Intermediate Similarity	NPD4730	Approved
0.789	Intermediate Similarity	NPD6274	Approved
0.7872	Intermediate Similarity	NPD5329	Approved
0.7838	Intermediate Similarity	NPD7101	Approved
0.7838	Intermediate Similarity	NPD7100	Approved
0.7822	Intermediate Similarity	NPD5696	Approved
0.7818	Intermediate Similarity	NPD6009	Approved
0.7818	Intermediate Similarity	NPD6317	Approved
0.7789	Intermediate Similarity	NPD6409	Approved
0.7789	Intermediate Similarity	NPD6684	Approved
0.7789	Intermediate Similarity	NPD7521	Approved
0.7789	Intermediate Similarity	NPD5280	Approved
0.7789	Intermediate Similarity	NPD7334	Approved
0.7789	Intermediate Similarity	NPD5330	Approved
0.7789	Intermediate Similarity	NPD5690	Phase 2
0.7789	Intermediate Similarity	NPD7146	Approved
0.7789	Intermediate Similarity	NPD4694	Approved
0.7766	Intermediate Similarity	NPD4197	Approved
0.7757	Intermediate Similarity	NPD5247	Approved
0.7757	Intermediate Similarity	NPD5248	Approved
0.7757	Intermediate Similarity	NPD5249	Phase 3
0.7757	Intermediate Similarity	NPD4634	Approved
0.7757	Intermediate Similarity	NPD5135	Approved
0.7757	Intermediate Similarity	NPD5169	Approved
0.7757	Intermediate Similarity	NPD5250	Approved
0.7757	Intermediate Similarity	NPD5251	Approved
0.7757	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5284	Approved
0.7755	Intermediate Similarity	NPD6050	Approved
0.7755	Intermediate Similarity	NPD5281	Approved
0.7748	Intermediate Similarity	NPD6313	Approved
0.7748	Intermediate Similarity	NPD6314	Approved
0.7732	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD6673	Approved
0.7732	Intermediate Similarity	NPD6080	Approved
0.7732	Intermediate Similarity	NPD6904	Approved
0.7723	Intermediate Similarity	NPD7902	Approved
0.7714	Intermediate Similarity	NPD6008	Approved
0.77	Intermediate Similarity	NPD4629	Approved
0.77	Intermediate Similarity	NPD5210	Approved
0.7699	Intermediate Similarity	NPD6909	Approved
0.7699	Intermediate Similarity	NPD6908	Approved
0.7692	Intermediate Similarity	NPD3617	Approved
0.7685	Intermediate Similarity	NPD5215	Approved
0.7685	Intermediate Similarity	NPD5217	Approved
0.7685	Intermediate Similarity	NPD5216	Approved
0.7685	Intermediate Similarity	NPD5127	Approved
0.7653	Intermediate Similarity	NPD5692	Phase 3
0.7647	Intermediate Similarity	NPD7638	Approved
0.7629	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6903	Approved
0.7611	Intermediate Similarity	NPD6319	Approved
0.7579	Intermediate Similarity	NPD3668	Phase 3
0.7576	Intermediate Similarity	NPD8034	Phase 2
0.7576	Intermediate Similarity	NPD5694	Approved
0.7576	Intermediate Similarity	NPD8035	Phase 2
0.7576	Intermediate Similarity	NPD6411	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7565	Intermediate Similarity	NPD7604	Phase 2
0.7553	Intermediate Similarity	NPD4223	Phase 3
0.7553	Intermediate Similarity	NPD4221	Approved
0.7544	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5983	Phase 2
0.7527	Intermediate Similarity	NPD4695	Discontinued
0.7525	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD5167	Approved
0.7473	Intermediate Similarity	NPD6117	Approved
0.7456	Intermediate Similarity	NPD6059	Approved
0.7456	Intermediate Similarity	NPD6054	Approved
0.7436	Intermediate Similarity	NPD6336	Discontinued
0.7436	Intermediate Similarity	NPD6616	Approved
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6098	Approved
0.74	Intermediate Similarity	NPD5693	Phase 1
0.7391	Intermediate Similarity	NPD6116	Phase 1
0.7374	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6101	Approved
0.7373	Intermediate Similarity	NPD7078	Approved
0.7373	Intermediate Similarity	NPD8293	Discontinued
0.7363	Intermediate Similarity	NPD6942	Approved
0.7363	Intermediate Similarity	NPD7339	Approved
0.7347	Intermediate Similarity	NPD3573	Approved
0.734	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7525	Registered
0.7328	Intermediate Similarity	NPD6370	Approved
0.7312	Intermediate Similarity	NPD6115	Approved
0.7312	Intermediate Similarity	NPD6118	Approved
0.7312	Intermediate Similarity	NPD6697	Approved
0.7312	Intermediate Similarity	NPD6114	Approved
0.7311	Intermediate Similarity	NPD7736	Approved
0.7292	Intermediate Similarity	NPD4788	Approved
0.7253	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4138	Approved
0.7245	Intermediate Similarity	NPD4690	Approved
0.7245	Intermediate Similarity	NPD4693	Phase 3
0.7245	Intermediate Similarity	NPD5205	Approved
0.7245	Intermediate Similarity	NPD4689	Approved
0.7245	Intermediate Similarity	NPD4688	Approved
0.7241	Intermediate Similarity	NPD6016	Approved
0.7241	Intermediate Similarity	NPD6015	Approved
0.7184	Intermediate Similarity	NPD5654	Approved
0.7179	Intermediate Similarity	NPD5988	Approved
0.7157	Intermediate Similarity	NPD5133	Approved
0.7129	Intermediate Similarity	NPD5207	Approved
0.7128	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.71	Intermediate Similarity	NPD5208	Approved
0.7097	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6001	Approved
0.7083	Intermediate Similarity	NPD4139	Approved
0.7083	Intermediate Similarity	NPD4692	Approved
0.7065	Intermediate Similarity	NPD5733	Approved
0.7048	Intermediate Similarity	NPD5959	Approved
0.7033	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6033	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.6991	Remote Similarity	NPD6053	Discontinued
0.699	Remote Similarity	NPD5779	Approved
0.699	Remote Similarity	NPD5778	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