NPASS Compound

Structure

CID269923 OpenBabel06191716072D 24 26 0 0 1 0 0 0 0 0999 V2000 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	350.785
LogP:	2.725
LogD:	1.709
LogS:	-3.763
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.868
Synthetic Accessibility Score:	3.735
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.015
MDCK Permeability:	2.305171983607579e-05
Pgp-inhibitor:	0.058
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	80.74111938476562%
Volume Distribution (VD):	0.395
Pgp-substrate:	19.76970100402832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.616
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	0.696
Half-life (T1/2):	0.409

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.324
Carcinogencity:	0.194
Eye Corrosion:	0.004
Eye Irritation:	0.096
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC269923

Natural Product ID:	NPC269923
*Common Name:**	7-Oxo-15-Hydroxydehydroabietic Acid
IUPAC Name:	(1R,4aS,10aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-9-oxo-3,4,10,10a-tetrahydro-2H-phenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	MXPXAZNVQUWDFH-NSISKUIASA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-18(2,24)12-6-7-14-13(10-12)15(21)11-16-19(14,3)8-5-9-20(16,4)17(22)23/h6-7,10,16,24H,5,8-9,11H2,1-4H3,(H,22,23)/t16-,19-,20-/m1/s1
SMILES:	CC(C)(c1ccc2c(c1)C(=O)C[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL597920
PubChem CID:	14017925
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2089121]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	sclerotium	n.a.	PMID[21250700]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	trunk	n.a.	n.a.	PMID[24224862]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	Trunk	n.a.	n.a.	PMID[26812172]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30063340]
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[32633512]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379416]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3443857]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3760882]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3841557]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288443]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	PMID[8133299]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8133299]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8691212]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO22470	Corynebacterium glutamicum	Species	Corynebacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[Article]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30645	Poria cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17292	Asparagus racemosus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9311	Parkia clappertoniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21014	Brucea antidysenterica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO822	Cressa cretica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10588	Diploschistes violarius	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21165	Phagnalon atlanticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9051	Delesseria sanguinea	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12895	Polypodiodes niponica	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20619	Ougeinia dalbergioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22470	Corynebacterium glutamicum	Species	Corynebacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19502	Squamopappus skutchii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10177	Eria linearifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11832	Pinus banksiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5205	Gymnoascus reesii	Species	Gymnoascaceae	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	11
Others	7

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	4
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	44.0	ug.mL-1	PMID[476077]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[476077]
NPT80	Cell Line	Raji	Homo sapiens	Inhibition	=	60.0	%	PMID[476078]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100000.0	nM	PMID[476078]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	161.7	%	PMID[476079]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	94.6	%	PMID[476079]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[476079]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[476079]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[476077]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[476077]
NPT2	Others	Unspecified		IC50	=	238.0	molar ratio	PMID[476078]
NPT2	Others	Unspecified		Inhibition	=	93.4	%	PMID[476078]
NPT2	Others	Unspecified		Inhibition	=	69.1	%	PMID[476078]
NPT2	Others	Unspecified		Inhibition	=	19.5	%	PMID[476078]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[476078]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[476078]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[476079]

☑ 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 NPC269923 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	251
0.1-0.2	1281
0.2-0.3	2293
0.3-0.4	6481
0.4-0.5	12823
0.5-0.6	12192
0.6-0.7	6290
0.7-0.8	993
0.8-0.85	69
0.85-0.9	17
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167323
0.9828	High Similarity	NPC85511
0.9211	High Similarity	NPC471721
0.918	High Similarity	NPC51448
0.918	High Similarity	NPC115797
0.9138	High Similarity	NPC158157
0.9123	High Similarity	NPC93287
0.8947	High Similarity	NPC95126
0.8947	High Similarity	NPC475002
0.8803	High Similarity	NPC186933
0.876	High Similarity	NPC472981
0.8707	High Similarity	NPC280789
0.8707	High Similarity	NPC66208
0.8655	High Similarity	NPC212891
0.8644	High Similarity	NPC476357
0.8621	High Similarity	NPC474057
0.8537	High Similarity	NPC369
0.8537	High Similarity	NPC293831
0.8492	Intermediate Similarity	NPC474106
0.8487	Intermediate Similarity	NPC221275
0.8487	Intermediate Similarity	NPC215419
0.8462	Intermediate Similarity	NPC265513
0.8448	Intermediate Similarity	NPC318327
0.8443	Intermediate Similarity	NPC202015
0.8403	Intermediate Similarity	NPC196673
0.839	Intermediate Similarity	NPC471188
0.8374	Intermediate Similarity	NPC183339
0.8374	Intermediate Similarity	NPC234337
0.8374	Intermediate Similarity	NPC133389
0.8333	Intermediate Similarity	NPC93181
0.8333	Intermediate Similarity	NPC274839
0.8319	Intermediate Similarity	NPC143768
0.8281	Intermediate Similarity	NPC78364
0.8281	Intermediate Similarity	NPC69424
0.8281	Intermediate Similarity	NPC176130
0.8281	Intermediate Similarity	NPC84672
0.8279	Intermediate Similarity	NPC45794
0.8271	Intermediate Similarity	NPC472308
0.8254	Intermediate Similarity	NPC328107
0.8246	Intermediate Similarity	NPC25458
0.8246	Intermediate Similarity	NPC304873
0.8235	Intermediate Similarity	NPC292834
0.8231	Intermediate Similarity	NPC108129
0.8217	Intermediate Similarity	NPC229894
0.8211	Intermediate Similarity	NPC472698
0.8211	Intermediate Similarity	NPC472697
0.8205	Intermediate Similarity	NPC249811
0.8203	Intermediate Similarity	NPC253681
0.8197	Intermediate Similarity	NPC105141
0.8197	Intermediate Similarity	NPC469843
0.8197	Intermediate Similarity	NPC242764
0.8195	Intermediate Similarity	NPC477596
0.819	Intermediate Similarity	NPC105899
0.8189	Intermediate Similarity	NPC295664
0.8182	Intermediate Similarity	NPC477139
0.8174	Intermediate Similarity	NPC329556
0.8174	Intermediate Similarity	NPC255676
0.8174	Intermediate Similarity	NPC247976
0.8168	Intermediate Similarity	NPC18798
0.8158	Intermediate Similarity	NPC136810
0.8158	Intermediate Similarity	NPC128248
0.8158	Intermediate Similarity	NPC225079
0.8158	Intermediate Similarity	NPC133809
0.8154	Intermediate Similarity	NPC276238
0.8154	Intermediate Similarity	NPC117899
0.8154	Intermediate Similarity	NPC303910
0.8151	Intermediate Similarity	NPC133308
0.8145	Intermediate Similarity	NPC476645
0.814	Intermediate Similarity	NPC72667
0.813	Intermediate Similarity	NPC222968
0.813	Intermediate Similarity	NPC80605
0.813	Intermediate Similarity	NPC323440
0.8125	Intermediate Similarity	NPC470649
0.8125	Intermediate Similarity	NPC275576
0.8125	Intermediate Similarity	NPC478107
0.8125	Intermediate Similarity	NPC470765
0.812	Intermediate Similarity	NPC94751
0.812	Intermediate Similarity	NPC202225
0.812	Intermediate Similarity	NPC100767
0.812	Intermediate Similarity	NPC477594
0.812	Intermediate Similarity	NPC142326
0.811	Intermediate Similarity	NPC228739
0.8103	Intermediate Similarity	NPC329282
0.8103	Intermediate Similarity	NPC472221
0.8103	Intermediate Similarity	NPC472222
0.8099	Intermediate Similarity	NPC130591
0.8099	Intermediate Similarity	NPC234637
0.8092	Intermediate Similarity	NPC472682
0.8092	Intermediate Similarity	NPC472692
0.8087	Intermediate Similarity	NPC284477
0.8077	Intermediate Similarity	NPC193203
0.8074	Intermediate Similarity	NPC475957
0.807	Intermediate Similarity	NPC217621
0.8062	Intermediate Similarity	NPC470753
0.8062	Intermediate Similarity	NPC473220
0.8062	Intermediate Similarity	NPC254492
0.8062	Intermediate Similarity	NPC169913
0.8045	Intermediate Similarity	NPC126516
0.8045	Intermediate Similarity	NPC329913
0.8034	Intermediate Similarity	NPC471186
0.803	Intermediate Similarity	NPC471851
0.8029	Intermediate Similarity	NPC315578
0.8017	Intermediate Similarity	NPC471481
0.8017	Intermediate Similarity	NPC470253
0.8016	Intermediate Similarity	NPC476234
0.8015	Intermediate Similarity	NPC471832
0.8015	Intermediate Similarity	NPC4214
0.8015	Intermediate Similarity	NPC25736
0.8015	Intermediate Similarity	NPC171460
0.8	Intermediate Similarity	NPC204784
0.8	Intermediate Similarity	NPC472708
0.7985	Intermediate Similarity	NPC23894
0.7985	Intermediate Similarity	NPC474659
0.7984	Intermediate Similarity	NPC228318
0.7982	Intermediate Similarity	NPC229242
0.7969	Intermediate Similarity	NPC51079
0.7969	Intermediate Similarity	NPC318067
0.7969	Intermediate Similarity	NPC275145
0.7966	Intermediate Similarity	NPC37914
0.7956	Intermediate Similarity	NPC26924
0.7951	Intermediate Similarity	NPC294458
0.7941	Intermediate Similarity	NPC477592
0.7939	Intermediate Similarity	NPC96024
0.7937	Intermediate Similarity	NPC232958
0.7934	Intermediate Similarity	NPC218855
0.7926	Intermediate Similarity	NPC80035
0.792	Intermediate Similarity	NPC318173
0.792	Intermediate Similarity	NPC254233
0.7913	Intermediate Similarity	NPC228435
0.791	Intermediate Similarity	NPC78307
0.791	Intermediate Similarity	NPC115458
0.791	Intermediate Similarity	NPC111845
0.7907	Intermediate Similarity	NPC199273
0.7895	Intermediate Similarity	NPC253423
0.7887	Intermediate Similarity	NPC5568
0.7886	Intermediate Similarity	NPC474095
0.7883	Intermediate Similarity	NPC477593
0.7868	Intermediate Similarity	NPC474311
0.7863	Intermediate Similarity	NPC19856
0.7857	Intermediate Similarity	NPC42657
0.7852	Intermediate Similarity	NPC288089
0.7852	Intermediate Similarity	NPC477896
0.7852	Intermediate Similarity	NPC477893
0.7845	Intermediate Similarity	NPC109514
0.7829	Intermediate Similarity	NPC472704
0.7829	Intermediate Similarity	NPC472681
0.7812	Intermediate Similarity	NPC249340
0.7812	Intermediate Similarity	NPC162935
0.7807	Intermediate Similarity	NPC185208
0.7807	Intermediate Similarity	NPC219573
0.7807	Intermediate Similarity	NPC61944
0.7805	Intermediate Similarity	NPC326664
0.7803	Intermediate Similarity	NPC3009
0.7803	Intermediate Similarity	NPC48248
0.7795	Intermediate Similarity	NPC238861
0.7795	Intermediate Similarity	NPC77000
0.7794	Intermediate Similarity	NPC153088
0.7787	Intermediate Similarity	NPC186128
0.7786	Intermediate Similarity	NPC473751
0.7786	Intermediate Similarity	NPC470648
0.7778	Intermediate Similarity	NPC474310
0.7778	Intermediate Similarity	NPC310662
0.7778	Intermediate Similarity	NPC138472
0.7778	Intermediate Similarity	NPC203486
0.7761	Intermediate Similarity	NPC17083
0.7759	Intermediate Similarity	NPC221825
0.7754	Intermediate Similarity	NPC13715
0.7754	Intermediate Similarity	NPC471974
0.7754	Intermediate Similarity	NPC469680
0.7754	Intermediate Similarity	NPC469681
0.7752	Intermediate Similarity	NPC472703
0.7752	Intermediate Similarity	NPC223351
0.7752	Intermediate Similarity	NPC282577
0.7752	Intermediate Similarity	NPC91478
0.7744	Intermediate Similarity	NPC262819
0.7739	Intermediate Similarity	NPC239185
0.7737	Intermediate Similarity	NPC272268
0.7734	Intermediate Similarity	NPC241001
0.7731	Intermediate Similarity	NPC172483
0.773	Intermediate Similarity	NPC66593
0.7727	Intermediate Similarity	NPC268607
0.7727	Intermediate Similarity	NPC472678
0.7724	Intermediate Similarity	NPC315520
0.7714	Intermediate Similarity	NPC477894
0.7714	Intermediate Similarity	NPC477595
0.771	Intermediate Similarity	NPC123506
0.771	Intermediate Similarity	NPC137416
0.7705	Intermediate Similarity	NPC210089
0.7704	Intermediate Similarity	NPC472656
0.7698	Intermediate Similarity	NPC294330
0.7698	Intermediate Similarity	NPC268930
0.7692	Intermediate Similarity	NPC476993
0.7692	Intermediate Similarity	NPC174991
0.7692	Intermediate Similarity	NPC12881
0.7692	Intermediate Similarity	NPC140118
0.7692	Intermediate Similarity	NPC77691
0.7692	Intermediate Similarity	NPC282895
0.7687	Intermediate Similarity	NPC72915
0.7686	Intermediate Similarity	NPC470252
0.7681	Intermediate Similarity	NPC118366

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 NPC269923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	865
0.2-0.3	1224
0.3-0.4	2529
0.4-0.5	2561
0.5-0.6	1323
0.6-0.7	337
0.7-0.8	58
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD5951	Approved
0.8678	High Similarity	NPD7163	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8174	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8174	Intermediate Similarity	NPD1929	Approved
0.8174	Intermediate Similarity	NPD1930	Approved
0.8154	Intermediate Similarity	NPD7008	Discontinued
0.807	Intermediate Similarity	NPD2066	Phase 3
0.7851	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD3495	Discontinued
0.7698	Intermediate Similarity	NPD7610	Discontinued
0.7627	Intermediate Similarity	NPD1932	Approved
0.7615	Intermediate Similarity	NPD4878	Approved
0.7606	Intermediate Similarity	NPD7236	Approved
0.7589	Intermediate Similarity	NPD7003	Approved
0.7544	Intermediate Similarity	NPD1088	Approved
0.7541	Intermediate Similarity	NPD2329	Discontinued
0.7519	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD7009	Phase 2
0.75	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7239	Suspended
0.746	Intermediate Similarity	NPD2629	Approved
0.7442	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5406	Approved
0.7429	Intermediate Similarity	NPD5408	Approved
0.7429	Intermediate Similarity	NPD5404	Approved
0.7429	Intermediate Similarity	NPD5405	Approved
0.7424	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7458	Discontinued
0.7414	Intermediate Similarity	NPD1693	Approved
0.7414	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6287	Discontinued
0.7385	Intermediate Similarity	NPD2932	Approved
0.7372	Intermediate Similarity	NPD7961	Discontinued
0.7368	Intermediate Similarity	NPD1089	Approved
0.7368	Intermediate Similarity	NPD1086	Approved
0.7368	Intermediate Similarity	NPD9258	Approved
0.7368	Intermediate Similarity	NPD9256	Approved
0.7368	Intermediate Similarity	NPD1090	Approved
0.7355	Intermediate Similarity	NPD1237	Approved
0.7353	Intermediate Similarity	NPD6966	Discovery
0.7328	Intermediate Similarity	NPD1202	Approved
0.7313	Intermediate Similarity	NPD1470	Approved
0.7299	Intermediate Similarity	NPD3764	Approved
0.7297	Intermediate Similarity	NPD3226	Approved
0.7281	Intermediate Similarity	NPD800	Approved
0.728	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4198	Discontinued
0.7265	Intermediate Similarity	NPD6049	Phase 2
0.7265	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD2182	Approved
0.7254	Intermediate Similarity	NPD2346	Discontinued
0.7246	Intermediate Similarity	NPD7714	Approved
0.7246	Intermediate Similarity	NPD7715	Approved
0.7234	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD164	Approved
0.7213	Intermediate Similarity	NPD5909	Discontinued
0.72	Intermediate Similarity	NPD1317	Discontinued
0.7197	Intermediate Similarity	NPD4879	Approved
0.7197	Intermediate Similarity	NPD3023	Approved
0.7197	Intermediate Similarity	NPD3026	Approved
0.7197	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3025	Approved
0.7176	Intermediate Similarity	NPD3024	Approved
0.7165	Intermediate Similarity	NPD6858	Approved
0.7165	Intermediate Similarity	NPD7094	Approved
0.7155	Intermediate Similarity	NPD1239	Approved
0.7143	Intermediate Similarity	NPD1566	Phase 3
0.7143	Intermediate Similarity	NPD1565	Approved
0.7143	Intermediate Similarity	NPD1564	Approved
0.7133	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6663	Approved
0.7121	Intermediate Similarity	NPD2345	Approved
0.7105	Intermediate Similarity	NPD1087	Approved
0.7103	Intermediate Similarity	NPD4628	Phase 3
0.7103	Intermediate Similarity	NPD8166	Discontinued
0.7094	Intermediate Similarity	NPD7631	Approved
0.709	Intermediate Similarity	NPD3972	Approved
0.708	Intermediate Similarity	NPD5736	Approved
0.7054	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3268	Approved
0.7018	Intermediate Similarity	NPD9259	Approved
0.7018	Intermediate Similarity	NPD9257	Approved
0.7013	Intermediate Similarity	NPD7058	Phase 2
0.7013	Intermediate Similarity	NPD7057	Phase 3
0.7009	Intermediate Similarity	NPD7609	Phase 3
0.7007	Intermediate Similarity	NPD4980	Approved
0.7	Intermediate Similarity	NPD3317	Approved
0.6993	Remote Similarity	NPD7305	Phase 1
0.6993	Remote Similarity	NPD2799	Discontinued
0.6993	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6647	Phase 2
0.6992	Remote Similarity	NPD4199	Phase 3
0.6985	Remote Similarity	NPD1283	Approved
0.698	Remote Similarity	NPD6273	Approved
0.6959	Remote Similarity	NPD7390	Discontinued
0.6954	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD9508	Approved
0.6934	Remote Similarity	NPD1164	Approved
0.6929	Remote Similarity	NPD2313	Discontinued
0.6917	Remote Similarity	NPD1989	Approved
0.6905	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD5277	Phase 2
0.6891	Remote Similarity	NPD1563	Approved
0.6885	Remote Similarity	NPD1238	Approved
0.6884	Remote Similarity	NPD2798	Approved
0.6875	Remote Similarity	NPD4308	Phase 3
0.6866	Remote Similarity	NPD5306	Approved
0.6866	Remote Similarity	NPD5305	Approved
0.6846	Remote Similarity	NPD6010	Discontinued
0.6842	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5086	Approved
0.6818	Remote Similarity	NPD405	Clinical (unspecified phase)
0.681	Remote Similarity	NPD650	Approved
0.6803	Remote Similarity	NPD9495	Approved
0.6791	Remote Similarity	NPD4102	Approved
0.6791	Remote Similarity	NPD4105	Approved
0.6788	Remote Similarity	NPD5157	Phase 1
0.6788	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5159	Phase 2
0.6783	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD3300	Phase 2
0.6765	Remote Similarity	NPD1281	Approved
0.6765	Remote Similarity	NPD4806	Approved
0.6765	Remote Similarity	NPD4807	Approved
0.6761	Remote Similarity	NPD8032	Phase 2
0.6757	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD9491	Approved
0.6754	Remote Similarity	NPD3971	Phase 1
0.6753	Remote Similarity	NPD7411	Suspended
0.6746	Remote Similarity	NPD5048	Discontinued
0.6741	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1888	Phase 1
0.6736	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7799	Discontinued
0.6718	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7741	Discontinued
0.6716	Remote Similarity	NPD9545	Approved
0.6712	Remote Similarity	NPD2935	Discontinued
0.6695	Remote Similarity	NPD5347	Phase 2
0.6695	Remote Similarity	NPD5346	Phase 2
0.6691	Remote Similarity	NPD3266	Approved
0.6691	Remote Similarity	NPD3267	Approved
0.6691	Remote Similarity	NPD4136	Approved
0.6691	Remote Similarity	NPD4135	Approved
0.6691	Remote Similarity	NPD4106	Approved
0.6691	Remote Similarity	NPD2797	Approved
0.6689	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD1245	Approved
0.6667	Remote Similarity	NPD7819	Suspended
0.6644	Remote Similarity	NPD3750	Approved
0.6643	Remote Similarity	NPD6085	Phase 2
0.6643	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7713	Phase 3
0.6641	Remote Similarity	NPD9263	Approved
0.6641	Remote Similarity	NPD7635	Approved
0.6641	Remote Similarity	NPD9264	Approved
0.6641	Remote Similarity	NPD9267	Approved
0.6641	Remote Similarity	NPD2342	Discontinued
0.6624	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1876	Approved
0.6618	Remote Similarity	NPD4059	Approved
0.6618	Remote Similarity	NPD4626	Approved
0.6599	Remote Similarity	NPD6100	Approved
0.6599	Remote Similarity	NPD6099	Approved
0.6597	Remote Similarity	NPD4307	Phase 2
0.6597	Remote Similarity	NPD2979	Phase 3
0.6594	Remote Similarity	NPD1608	Approved
0.6594	Remote Similarity	NPD6637	Approved
0.6593	Remote Similarity	NPD3091	Approved
0.6589	Remote Similarity	NPD74	Approved
0.6589	Remote Similarity	NPD9266	Approved
0.6584	Remote Similarity	NPD6232	Discontinued
0.6579	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD226	Approved
0.6573	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD9493	Approved
0.6557	Remote Similarity	NPD9260	Approved
0.6554	Remote Similarity	NPD1471	Phase 3
0.6547	Remote Similarity	NPD1755	Approved
0.6544	Remote Similarity	NPD1651	Approved
0.6541	Remote Similarity	NPD1246	Approved
0.6529	Remote Similarity	NPD1508	Approved
0.6525	Remote Similarity	NPD4793	Discontinued
0.6524	Remote Similarity	NPD7177	Discontinued
0.6522	Remote Similarity	NPD5618	Discontinued
0.6519	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD8165	Discontinued
0.6507	Remote Similarity	NPD6817	Clinical (unspecified phase)

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