NPASS Compound

Structure

CID249040 OpenBabel06191716052D 23 27 0 0 1 0 0 0 0 0999 V2000 -5.6333 -0.7590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8288 -1.3424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4620 -0.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6417 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6418 -1.8951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3392 0.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6410 -1.8953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7163 -0.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6769 -1.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0137 -0.5324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4621 -1.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9426 -0.1966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8209 -1.4215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8202 -1.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9970 -0.9250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8209 -0.4736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4614 -1.4217 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6412 -0.0001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8203 -0.4737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4615 -0.4738 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.5143 -1.9042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2143 -1.8556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 10 2 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 16 1 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 14 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 11 23 1 0 0 0 0 12 6 1 1 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 19 2 0 0 0 0 15 9 1 6 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 6 0 0 0 18 19 1 0 0 0 0 18 21 1 6 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.17
Volume:	320.79
LogP:	2.561
LogD:	2.695
LogS:	-2.991
# Rotatable Bonds:	1
TPSA:	59.49
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	5.294
Fsp3:	0.474
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:	-5.088
MDCK Permeability:	1.1223466572118923e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.664
Human Intestinal Absorption (HIA):	0.87
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	0.197

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.742
Plasma Protein Binding (PPB):	81.6025161743164%
Volume Distribution (VD):	1.67
Pgp-substrate:	14.842231750488281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.631
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.252
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.835
CYP2D6-inhibitor:	0.252
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.422
CYP3A4-substrate:	0.626

ADMET: Excretion

Clearance (CL):	11.438
Half-life (T1/2):	0.668

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.361
Carcinogencity:	0.951
Eye Corrosion:	0.012
Eye Irritation:	0.036
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC249040

Natural Product ID:	NPC249040
*Common Name:**	Sarpagine
IUPAC Name:	n.a.
Synonyms:	Sarpagine
Standard InCHIKey:	VTVQHYQGTTVKDE-QDHOPYFXSA-N
Standard InCHI:	InChI=1S/C19H22N2O2/c1-2-10-8-21-17-7-14-13-5-11(23)3-4-16(13)20-19(14)18(21)6-12(10)15(17)9-22/h2-5,12,15,17-18,20,22-23H,6-9H2,1H3/b10-2-/t12-,15-,17+,18+/m1/s1
SMILES:	OC[C@H]1[C@@H]2Cc3c([C@H]4N2C/C(=C/C)/[C@H]1C4)[nH]c1c3cc(O)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498733
PubChem CID:	44592554
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline alkaloids

*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
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/01496395.2011.635623]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11914965]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27116034]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667821]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10333	Rauvolfia caffra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5135	Rauvolfia perakensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20258	Alstonia mairei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6275	Rauvolfia cumminsii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31253	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10333	Rauvolfia caffra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20258	Alstonia mairei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5135	Rauvolfia perakensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6275	Rauvolfia cumminsii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31253	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5135	Rauvolfia perakensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20258	Alstonia mairei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21963	Hypericum japonicum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20258	Alstonia mairei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21963	Hypericum japonicum	Species	Hypericaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[496450]

☑ 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 NPC249040 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	426
0.1-0.2	2125
0.2-0.3	12023
0.3-0.4	13228
0.4-0.5	9032
0.5-0.6	3378
0.6-0.7	1797
0.7-0.8	616
0.8-0.85	54
0.85-0.9	14
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8854	High Similarity	NPC476116
0.8806	High Similarity	NPC470126
0.8762	High Similarity	NPC253580
0.8757	High Similarity	NPC472123
0.8731	High Similarity	NPC476041
0.8731	High Similarity	NPC304926
0.87	High Similarity	NPC280272
0.8698	High Similarity	NPC472111
0.8646	High Similarity	NPC475070
0.8615	High Similarity	NPC5145
0.8588	High Similarity	NPC317430
0.8534	High Similarity	NPC329793
0.8525	High Similarity	NPC472108
0.8525	High Similarity	NPC139291
0.8486	Intermediate Similarity	NPC171171
0.8485	Intermediate Similarity	NPC469592
0.8485	Intermediate Similarity	NPC471080
0.8432	Intermediate Similarity	NPC314002
0.8418	Intermediate Similarity	NPC475910
0.841	Intermediate Similarity	NPC474145
0.841	Intermediate Similarity	NPC475841
0.8402	Intermediate Similarity	NPC223427
0.8402	Intermediate Similarity	NPC476098
0.84	Intermediate Similarity	NPC469928
0.84	Intermediate Similarity	NPC183407
0.8378	Intermediate Similarity	NPC204717
0.8361	Intermediate Similarity	NPC88363
0.836	Intermediate Similarity	NPC99666
0.8324	Intermediate Similarity	NPC220765
0.8317	Intermediate Similarity	NPC469594
0.8261	Intermediate Similarity	NPC72980
0.8254	Intermediate Similarity	NPC469501
0.8254	Intermediate Similarity	NPC469470
0.8246	Intermediate Similarity	NPC295228
0.8226	Intermediate Similarity	NPC472109
0.8226	Intermediate Similarity	NPC472110
0.8209	Intermediate Similarity	NPC478074
0.8201	Intermediate Similarity	NPC128751
0.8201	Intermediate Similarity	NPC246700
0.8182	Intermediate Similarity	NPC53344
0.8177	Intermediate Similarity	NPC276517
0.8173	Intermediate Similarity	NPC6215
0.816	Intermediate Similarity	NPC477549
0.8158	Intermediate Similarity	NPC106833
0.8158	Intermediate Similarity	NPC469497
0.8146	Intermediate Similarity	NPC472099
0.8135	Intermediate Similarity	NPC251090
0.8128	Intermediate Similarity	NPC176127
0.8108	Intermediate Similarity	NPC184964
0.8108	Intermediate Similarity	NPC326575
0.8093	Intermediate Similarity	NPC77555
0.8093	Intermediate Similarity	NPC153042
0.809	Intermediate Similarity	NPC270918
0.8081	Intermediate Similarity	NPC118832
0.8081	Intermediate Similarity	NPC47059
0.8081	Intermediate Similarity	NPC329708
0.8081	Intermediate Similarity	NPC264166
0.8081	Intermediate Similarity	NPC274291
0.8081	Intermediate Similarity	NPC165349
0.8065	Intermediate Similarity	NPC133261
0.806	Intermediate Similarity	NPC471304
0.8054	Intermediate Similarity	NPC24594
0.8054	Intermediate Similarity	NPC472122
0.8053	Intermediate Similarity	NPC46580
0.8045	Intermediate Similarity	NPC84508
0.8043	Intermediate Similarity	NPC474409
0.8032	Intermediate Similarity	NPC19679
0.8031	Intermediate Similarity	NPC307963
0.8021	Intermediate Similarity	NPC472105
0.8021	Intermediate Similarity	NPC187827
0.801	Intermediate Similarity	NPC469589
0.801	Intermediate Similarity	NPC213530
0.801	Intermediate Similarity	NPC193267
0.8	Intermediate Similarity	NPC189812
0.8	Intermediate Similarity	NPC156704
0.8	Intermediate Similarity	NPC329688
0.799	Intermediate Similarity	NPC470500
0.7979	Intermediate Similarity	NPC314394
0.797	Intermediate Similarity	NPC176538
0.797	Intermediate Similarity	NPC329747
0.7959	Intermediate Similarity	NPC52557
0.7951	Intermediate Similarity	NPC152768
0.7951	Intermediate Similarity	NPC330009
0.7951	Intermediate Similarity	NPC148183
0.7947	Intermediate Similarity	NPC94943
0.7927	Intermediate Similarity	NPC92111
0.7926	Intermediate Similarity	NPC81175
0.7919	Intermediate Similarity	NPC476167
0.7917	Intermediate Similarity	NPC32771
0.7895	Intermediate Similarity	NPC472294
0.7895	Intermediate Similarity	NPC162748
0.7895	Intermediate Similarity	NPC190007
0.7892	Intermediate Similarity	NPC472098
0.7887	Intermediate Similarity	NPC324149
0.7882	Intermediate Similarity	NPC475422
0.7879	Intermediate Similarity	NPC315491
0.7879	Intermediate Similarity	NPC45459
0.7876	Intermediate Similarity	NPC472112
0.7876	Intermediate Similarity	NPC76748
0.7874	Intermediate Similarity	NPC96321
0.7872	Intermediate Similarity	NPC232340
0.7868	Intermediate Similarity	NPC192315
0.7864	Intermediate Similarity	NPC477110
0.7861	Intermediate Similarity	NPC203754
0.7861	Intermediate Similarity	NPC150048
0.785	Intermediate Similarity	NPC474192
0.785	Intermediate Similarity	NPC475720
0.7842	Intermediate Similarity	NPC212535
0.7837	Intermediate Similarity	NPC255110
0.7834	Intermediate Similarity	NPC41679
0.7824	Intermediate Similarity	NPC175474
0.7824	Intermediate Similarity	NPC296527
0.7822	Intermediate Similarity	NPC88008
0.7822	Intermediate Similarity	NPC193777
0.7806	Intermediate Similarity	NPC326634
0.7804	Intermediate Similarity	NPC476451
0.7802	Intermediate Similarity	NPC255229
0.7802	Intermediate Similarity	NPC81229
0.78	Intermediate Similarity	NPC199277
0.78	Intermediate Similarity	NPC211813
0.78	Intermediate Similarity	NPC135887
0.7799	Intermediate Similarity	NPC132642
0.7795	Intermediate Similarity	NPC472113
0.7789	Intermediate Similarity	NPC195461
0.7789	Intermediate Similarity	NPC81654
0.7789	Intermediate Similarity	NPC313985
0.7789	Intermediate Similarity	NPC213308
0.7789	Intermediate Similarity	NPC249150
0.7789	Intermediate Similarity	NPC49196
0.7789	Intermediate Similarity	NPC79129
0.7784	Intermediate Similarity	NPC95783
0.7783	Intermediate Similarity	NPC87755
0.7783	Intermediate Similarity	NPC477111
0.7778	Intermediate Similarity	NPC50503
0.7778	Intermediate Similarity	NPC306376
0.7778	Intermediate Similarity	NPC472443
0.7767	Intermediate Similarity	NPC266931
0.7754	Intermediate Similarity	NPC471294
0.7754	Intermediate Similarity	NPC34508
0.774	Intermediate Similarity	NPC305984
0.7737	Intermediate Similarity	NPC15840
0.7736	Intermediate Similarity	NPC21638
0.7727	Intermediate Similarity	NPC70956
0.7727	Intermediate Similarity	NPC243834
0.7718	Intermediate Similarity	NPC316981
0.7717	Intermediate Similarity	NPC477861
0.7717	Intermediate Similarity	NPC476118
0.771	Intermediate Similarity	NPC311906
0.7708	Intermediate Similarity	NPC84478
0.7707	Intermediate Similarity	NPC167860
0.7707	Intermediate Similarity	NPC123976
0.7701	Intermediate Similarity	NPC158129
0.77	Intermediate Similarity	NPC60006
0.77	Intermediate Similarity	NPC214142
0.7681	Intermediate Similarity	NPC477610
0.7681	Intermediate Similarity	NPC151781
0.7681	Intermediate Similarity	NPC74562
0.7681	Intermediate Similarity	NPC316181
0.7677	Intermediate Similarity	NPC242209
0.7671	Intermediate Similarity	NPC470784
0.767	Intermediate Similarity	NPC208284
0.767	Intermediate Similarity	NPC9894
0.7665	Intermediate Similarity	NPC106937
0.7664	Intermediate Similarity	NPC261251
0.7664	Intermediate Similarity	NPC478078
0.766	Intermediate Similarity	NPC259545
0.7656	Intermediate Similarity	NPC472444
0.7656	Intermediate Similarity	NPC48938
0.765	Intermediate Similarity	NPC128823
0.7647	Intermediate Similarity	NPC126481
0.7641	Intermediate Similarity	NPC196251
0.7641	Intermediate Similarity	NPC102338
0.7641	Intermediate Similarity	NPC111602
0.7641	Intermediate Similarity	NPC63199
0.7638	Intermediate Similarity	NPC474188
0.7637	Intermediate Similarity	NPC285469
0.7637	Intermediate Similarity	NPC141353
0.7636	Intermediate Similarity	NPC475816
0.7635	Intermediate Similarity	NPC285558
0.7633	Intermediate Similarity	NPC219087
0.7633	Intermediate Similarity	NPC48353
0.7632	Intermediate Similarity	NPC96890
0.7628	Intermediate Similarity	NPC100547
0.7628	Intermediate Similarity	NPC314954
0.7626	Intermediate Similarity	NPC131017
0.7622	Intermediate Similarity	NPC102423
0.7617	Intermediate Similarity	NPC319232
0.7617	Intermediate Similarity	NPC24370
0.7608	Intermediate Similarity	NPC74969
0.7598	Intermediate Similarity	NPC477113
0.7594	Intermediate Similarity	NPC310118
0.7593	Intermediate Similarity	NPC223409
0.7593	Intermediate Similarity	NPC95240
0.7593	Intermediate Similarity	NPC322135
0.7592	Intermediate Similarity	NPC270009
0.7589	Intermediate Similarity	NPC471891
0.7586	Intermediate Similarity	NPC162484
0.7581	Intermediate Similarity	NPC118559
0.7581	Intermediate Similarity	NPC304307
0.7581	Intermediate Similarity	NPC110151

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 NPC249040 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	561
0.2-0.3	795
0.3-0.4	1344
0.4-0.5	2493
0.5-0.6	2564
0.6-0.7	995
0.7-0.8	164
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
0.8413	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5658	Approved
0.8081	Intermediate Similarity	NPD4037	Approved
0.8081	Intermediate Similarity	NPD4122	Approved
0.8081	Intermediate Similarity	NPD31	Approved
0.8081	Intermediate Similarity	NPD32	Approved
0.8081	Intermediate Similarity	NPD4038	Approved
0.8081	Intermediate Similarity	NPD4033	Approved
0.8081	Intermediate Similarity	NPD4036	Approved
0.8081	Intermediate Similarity	NPD4035	Approved
0.8081	Intermediate Similarity	NPD4039	Approved
0.8081	Intermediate Similarity	NPD4034	Approved
0.8053	Intermediate Similarity	NPD2383	Phase 1
0.8039	Intermediate Similarity	NPD7112	Discontinued
0.8032	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD1038	Approved
0.801	Intermediate Similarity	NPD2175	Phase 3
0.801	Intermediate Similarity	NPD2176	Approved
0.801	Intermediate Similarity	NPD2177	Approved
0.8	Intermediate Similarity	NPD7222	Phase 2
0.799	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7951	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD7948	Phase 1
0.7879	Intermediate Similarity	NPD484	Approved
0.7846	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1325	Approved
0.7838	Intermediate Similarity	NPD1326	Approved
0.7789	Intermediate Similarity	NPD4204	Approved
0.7789	Intermediate Similarity	NPD4600	Approved
0.7789	Intermediate Similarity	NPD4601	Approved
0.7789	Intermediate Similarity	NPD4203	Approved
0.7783	Intermediate Similarity	NPD2916	Discontinued
0.7778	Intermediate Similarity	NPD5612	Discontinued
0.7772	Intermediate Similarity	NPD3003	Approved
0.7766	Intermediate Similarity	NPD2382	Approved
0.7766	Intermediate Similarity	NPD2380	Approved
0.7766	Intermediate Similarity	NPD2381	Approved
0.7756	Intermediate Similarity	NPD5936	Approved
0.7756	Intermediate Similarity	NPD5939	Approved
0.7751	Intermediate Similarity	NPD7194	Discontinued
0.775	Intermediate Similarity	NPD4511	Phase 1
0.7734	Intermediate Similarity	NPD7452	Approved
0.7734	Intermediate Similarity	NPD7453	Approved
0.7729	Intermediate Similarity	NPD4897	Phase 2
0.7725	Intermediate Similarity	NPD6159	Phase 2
0.7717	Intermediate Similarity	NPD5140	Approved
0.7717	Intermediate Similarity	NPD5138	Approved
0.7713	Intermediate Similarity	NPD5065	Approved
0.7703	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD5530	Phase 1
0.7678	Intermediate Similarity	NPD7726	Phase 1
0.7665	Intermediate Similarity	NPD802	Phase 2
0.7656	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD5596	Phase 2
0.765	Intermediate Similarity	NPD1768	Approved
0.765	Intermediate Similarity	NPD8395	Approved
0.765	Intermediate Similarity	NPD8396	Approved
0.7635	Intermediate Similarity	NPD4795	Phase 2
0.7633	Intermediate Similarity	NPD3330	Phase 1
0.7619	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD4502	Phase 2
0.7569	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6158	Phase 2
0.7569	Intermediate Similarity	NPD2882	Phase 1
0.7563	Intermediate Similarity	NPD5913	Phase 3
0.7563	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3814	Phase 1
0.7561	Intermediate Similarity	NPD6290	Phase 2
0.7559	Intermediate Similarity	NPD7221	Approved
0.7559	Intermediate Similarity	NPD7219	Approved
0.7535	Intermediate Similarity	NPD7603	Discontinued
0.7526	Intermediate Similarity	NPD6492	Phase 2
0.7525	Intermediate Similarity	NPD1739	Approved
0.7525	Intermediate Similarity	NPD4501	Approved
0.7525	Intermediate Similarity	NPD1740	Approved
0.7525	Intermediate Similarity	NPD4500	Approved
0.7523	Intermediate Similarity	NPD4885	Approved
0.7523	Intermediate Similarity	NPD7797	Approved
0.7523	Intermediate Similarity	NPD7796	Approved
0.7512	Intermediate Similarity	NPD5506	Approved
0.7512	Intermediate Similarity	NPD5507	Approved
0.75	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2762	Phase 2
0.7476	Intermediate Similarity	NPD5902	Approved
0.7476	Intermediate Similarity	NPD5903	Approved
0.7473	Intermediate Similarity	NPD1684	Approved
0.7473	Intermediate Similarity	NPD1685	Approved
0.745	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6376	Discontinued
0.7434	Intermediate Similarity	NPD8358	Approved
0.7409	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD5164	Discontinued
0.7398	Intermediate Similarity	NPD6227	Discontinued
0.7395	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1392	Approved
0.7391	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD5559	Phase 2
0.7376	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6985	Discontinued
0.7363	Intermediate Similarity	NPD4418	Discontinued
0.7356	Intermediate Similarity	NPD2189	Approved
0.7356	Intermediate Similarity	NPD2187	Approved
0.7352	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7558	Phase 2
0.7312	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD3825	Phase 3
0.7302	Intermediate Similarity	NPD6242	Discontinued
0.7302	Intermediate Similarity	NPD5930	Phase 3
0.7291	Intermediate Similarity	NPD5003	Discontinued
0.7282	Intermediate Similarity	NPD3928	Approved
0.7282	Intermediate Similarity	NPD3931	Approved
0.7282	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5256	Discontinued
0.7268	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3402	Phase 1
0.725	Intermediate Similarity	NPD4499	Approved
0.7248	Intermediate Similarity	NPD4401	Phase 2
0.7248	Intermediate Similarity	NPD4403	Phase 3
0.7246	Intermediate Similarity	NPD6991	Approved
0.7245	Intermediate Similarity	NPD7867	Phase 1
0.7244	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4076	Approved
0.7231	Intermediate Similarity	NPD4079	Approved
0.7228	Intermediate Similarity	NPD4463	Approved
0.7228	Intermediate Similarity	NPD4462	Approved
0.7222	Intermediate Similarity	NPD1592	Phase 3
0.72	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3389	Approved
0.7196	Intermediate Similarity	NPD3393	Approved
0.7196	Intermediate Similarity	NPD3394	Approved
0.7194	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6595	Phase 3
0.7192	Intermediate Similarity	NPD4602	Approved
0.7181	Intermediate Similarity	NPD5255	Approved
0.7179	Intermediate Similarity	NPD3506	Approved
0.7179	Intermediate Similarity	NPD3505	Approved
0.7178	Intermediate Similarity	NPD6569	Phase 2
0.7177	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD425	Approved
0.7173	Intermediate Similarity	NPD424	Approved
0.717	Intermediate Similarity	NPD5067	Phase 2
0.717	Intermediate Similarity	NPD5066	Phase 2
0.7157	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3477	Phase 2
0.7157	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5599	Discontinued
0.7143	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2794	Discontinued
0.7136	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2844	Phase 3
0.7128	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD926	Approved
0.712	Intermediate Similarity	NPD925	Approved
0.7118	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7672	Approved
0.7109	Intermediate Similarity	NPD7671	Approved
0.7108	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6494	Phase 2
0.7095	Intermediate Similarity	NPD8403	Phase 1
0.7095	Intermediate Similarity	NPD6403	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD3404	Approved
0.7091	Intermediate Similarity	NPD6246	Approved
0.7087	Intermediate Similarity	NPD2727	Phase 2
0.7083	Intermediate Similarity	NPD3440	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4044	Discontinued
0.7076	Intermediate Similarity	NPD7956	Approved
0.7076	Intermediate Similarity	NPD7955	Approved
0.7075	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3037	Phase 1
0.7068	Intermediate Similarity	NPD863	Approved
0.7068	Intermediate Similarity	NPD861	Approved
0.7068	Intermediate Similarity	NPD862	Approved
0.7065	Intermediate Similarity	NPD4951	Discontinued
0.7062	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3815	Phase 1
0.7056	Intermediate Similarity	NPD3816	Phase 1
0.7056	Intermediate Similarity	NPD3920	Phase 2
0.7056	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3082	Discontinued
0.7047	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5100	Phase 3
0.7039	Intermediate Similarity	NPD2952	Discontinued
0.703	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6978	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data