NPASS Compound

Structure

NPC37116 OpenBabel07101719512D 34 38 0 0 1 0 0 0 0 0999 V2000 -2.0074 -2.2294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9540 -1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 -2.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 -0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5962 -3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8774 -4.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0084 -2.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8774 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4133 -1.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 -5.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 -1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -3.4190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2793 -3.4190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1453 -4.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0113 -5.4190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4133 -4.9190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5962 -2.1100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0113 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4133 -3.9190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -2.4190 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1453 -3.9190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2872 -1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0113 -6.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -5.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0113 -2.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4951 -0.1808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 9 2 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 16 26 1 6 0 0 0 17 24 1 0 0 0 0 17 27 1 6 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 19 29 1 6 0 0 0 20 24 1 0 0 0 0 20 30 1 6 0 0 0 21 26 1 6 0 0 0 21 28 1 0 0 0 0 22 27 1 0 0 0 0 22 31 2 0 0 0 0 23 28 1 1 0 0 0 23 34 1 0 0 0 0 25 32 2 0 0 0 0 25 34 1 0 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.27
Volume:	489.621
LogP:	2.723
LogD:	1.859
LogS:	-4.172
# Rotatable Bonds:	2
TPSA:	97.74
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.613
Synthetic Accessibility Score:	5.107
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.759
MDCK Permeability:	1.7768643374438398e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.056
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.945
Plasma Protein Binding (PPB):	61.49696731567383%
Volume Distribution (VD):	0.491
Pgp-substrate:	21.94907569885254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.129
CYP2C19-substrate:	0.748
CYP2C9-inhibitor:	0.192
CYP2C9-substrate:	0.144
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.465
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.471

ADMET: Excretion

Clearance (CL):	10.543
Half-life (T1/2):	0.826

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.4
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.739
Skin Sensitization:	0.257
Carcinogencity:	0.865
Eye Corrosion:	0.005
Eye Irritation:	0.017
Respiratory Toxicity:	0.482

Download Data

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

Natural Product: NPC37116

Natural Product ID:	NPC37116
*Common Name:**	7-Hydroxy-14-Deoxywithanolide U
IUPAC Name:	(2R)-2-[(1R)-1-[(4S,7R,8S,9S,10R,13S,14S,17S)-4,7-dihydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	HMVXQIAJBGENDJ-MHYIOVDWSA-N
Standard InCHI:	InChI=1S/C28H38O6/c1-14-12-23(34-25(32)15(14)2)28(5,33)21-8-6-16-24-17(10-11-26(16,21)3)27(4)18(13-20(24)30)19(29)7-9-22(27)31/h7,9,13,16-17,19-21,23-24,29-30,33H,6,8,10-12H2,1-5H3/t16-,17-,19-,20-,21-,23+,24-,26-,27+,28+/m0/s1
SMILES:	O[C@H]1C=C2[C@@H](O)C=CC(=O)[C@@]2([C@@H]2[C@@H]1[C@@H]1CC[C@@H]([C@@]1(C)CC2)[C@]([C@H]1CC(=C(C(=O)O1)C)C)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463443
PubChem CID:	21679020
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO40122	Eriolarynx iochromoides	Species	Solanaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[31070367]
NPO27252	Iochroma australe	Species	Solanaceae	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
GI50	11
IC50	1
Others	12

Activity Type	# Activity
Cell Line	12
CELL-LINE	1
Individual Protein	2
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CQ	=	2.66	uM	PMID[474616]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.47	uM	PMID[474616]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	>	10000.0	nM	PMID[474617]
NPT396	Cell Line	T47D	Homo sapiens	GI50	>	10000.0	nM	PMID[474617]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	4100.0	nM	PMID[474617]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	5300.0	nM	PMID[474617]
NPT1723	Cell Line	HBL-100	Homo sapiens	GI50	=	4800.0	nM	PMID[474617]
NPT81	Cell Line	A549	Homo sapiens	GI50	>	10000.0	nM	PMID[474617]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	3400.0	nM	PMID[474617]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	3200.0	nM	PMID[474617]
NPT1577	Cell Line	SW1573	Homo sapiens	RatioGI50	=	0.9	n.a.	PMID[474617]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	4200.0	nM	PMID[474617]
NPT1577	Cell Line	SW1573	Homo sapiens	RatioGI50	=	0.8	n.a.	PMID[474617]
NPT2	Others	Unspecified		Ratio	=	3.5	n.a.	PMID[474616]
NPT27	Others	Unspecified		IC50	=	1660.0	nM	PMID[474616]
NPT2	Others	Unspecified		Ratio	=	0.62	n.a.	PMID[474616]
NPT23292	CELL-LINE	hTERT-BJ	Homo sapiens	GI50	>	10000.0	nM	PMID[474617]
NPT2	Others	Unspecified		RatioGI50	=	2.0	n.a.	PMID[474617]

☑ 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 NPC37116 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	194
0.1-0.2	1094
0.2-0.3	3756
0.3-0.4	8040
0.4-0.5	13010
0.5-0.6	6999
0.6-0.7	6860
0.7-0.8	2437
0.8-0.85	236
0.85-0.9	59
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9612	High Similarity	NPC473627
0.9434	High Similarity	NPC474181
0.9429	High Similarity	NPC236217
0.9245	High Similarity	NPC191620
0.9238	High Similarity	NPC29133
0.9151	High Similarity	NPC470961
0.9135	High Similarity	NPC91034
0.8991	High Similarity	NPC176840
0.8991	High Similarity	NPC190286
0.8929	High Similarity	NPC46570
0.8909	High Similarity	NPC20302
0.8909	High Similarity	NPC140055
0.8909	High Similarity	NPC167606
0.8909	High Similarity	NPC286528
0.8899	High Similarity	NPC147912
0.8899	High Similarity	NPC67259
0.885	High Similarity	NPC107493
0.8839	High Similarity	NPC79579
0.8829	High Similarity	NPC153440
0.8829	High Similarity	NPC709
0.8829	High Similarity	NPC50774
0.8829	High Similarity	NPC475913
0.8774	High Similarity	NPC475294
0.8772	High Similarity	NPC469789
0.875	High Similarity	NPC475834
0.875	High Similarity	NPC475041
0.875	High Similarity	NPC264954
0.875	High Similarity	NPC474179
0.875	High Similarity	NPC5292
0.8739	High Similarity	NPC312824
0.8739	High Similarity	NPC183580
0.8739	High Similarity	NPC470492
0.8739	High Similarity	NPC470493
0.8716	High Similarity	NPC221144
0.8696	High Similarity	NPC8369
0.8673	High Similarity	NPC474585
0.8673	High Similarity	NPC474370
0.8661	High Similarity	NPC186525
0.8654	High Similarity	NPC476223
0.8654	High Similarity	NPC310981
0.8654	High Similarity	NPC476240
0.8654	High Similarity	NPC224720
0.8649	High Similarity	NPC64318
0.8649	High Similarity	NPC270929
0.8641	High Similarity	NPC197386
0.8636	High Similarity	NPC122056
0.8627	High Similarity	NPC328371
0.8624	High Similarity	NPC474315
0.8621	High Similarity	NPC293112
0.8609	High Similarity	NPC11895
0.8596	High Similarity	NPC67569
0.8585	High Similarity	NPC255309
0.8584	High Similarity	NPC305260
0.8584	High Similarity	NPC270850
0.8571	High Similarity	NPC475320
0.8571	High Similarity	NPC470959
0.8571	High Similarity	NPC476965
0.8558	High Similarity	NPC287833
0.8558	High Similarity	NPC476274
0.8545	High Similarity	NPC100267
0.8545	High Similarity	NPC475524
0.8534	High Similarity	NPC172154
0.8534	High Similarity	NPC81736
0.8529	High Similarity	NPC174948
0.8529	High Similarity	NPC469995
0.8529	High Similarity	NPC318282
0.8529	High Similarity	NPC173875
0.8522	High Similarity	NPC470265
0.8522	High Similarity	NPC153700
0.8522	High Similarity	NPC269642
0.8522	High Similarity	NPC23786
0.8522	High Similarity	NPC88326
0.8522	High Similarity	NPC170538
0.8519	High Similarity	NPC220155
0.8505	High Similarity	NPC96377
0.8496	Intermediate Similarity	NPC311554
0.8496	Intermediate Similarity	NPC257457
0.8496	Intermediate Similarity	NPC329736
0.8491	Intermediate Similarity	NPC236390
0.8482	Intermediate Similarity	NPC148458
0.8462	Intermediate Similarity	NPC98868
0.8448	Intermediate Similarity	NPC473979
0.8431	Intermediate Similarity	NPC184870
0.8421	Intermediate Similarity	NPC473274
0.8421	Intermediate Similarity	NPC61520
0.8416	Intermediate Similarity	NPC303697
0.8407	Intermediate Similarity	NPC284068
0.8407	Intermediate Similarity	NPC471854
0.8396	Intermediate Similarity	NPC136289
0.8396	Intermediate Similarity	NPC119601
0.8396	Intermediate Similarity	NPC308726
0.8396	Intermediate Similarity	NPC195290
0.8396	Intermediate Similarity	NPC473424
0.8396	Intermediate Similarity	NPC204450
0.8393	Intermediate Similarity	NPC284915
0.8381	Intermediate Similarity	NPC51370
0.8381	Intermediate Similarity	NPC316964
0.8376	Intermediate Similarity	NPC3381
0.8376	Intermediate Similarity	NPC8374
0.8376	Intermediate Similarity	NPC470494
0.8365	Intermediate Similarity	NPC121339
0.8364	Intermediate Similarity	NPC5103
0.835	Intermediate Similarity	NPC171395
0.8348	Intermediate Similarity	NPC476961
0.8333	Intermediate Similarity	NPC323834
0.8333	Intermediate Similarity	NPC474736
0.8318	Intermediate Similarity	NPC111323
0.8318	Intermediate Similarity	NPC264048
0.8318	Intermediate Similarity	NPC470954
0.8305	Intermediate Similarity	NPC473635
0.8304	Intermediate Similarity	NPC25909
0.8304	Intermediate Similarity	NPC469454
0.8304	Intermediate Similarity	NPC469463
0.8304	Intermediate Similarity	NPC469496
0.8304	Intermediate Similarity	NPC250109
0.8302	Intermediate Similarity	NPC81530
0.8302	Intermediate Similarity	NPC99411
0.8302	Intermediate Similarity	NPC472924
0.8302	Intermediate Similarity	NPC163372
0.8302	Intermediate Similarity	NPC302537
0.8302	Intermediate Similarity	NPC474327
0.8291	Intermediate Similarity	NPC120724
0.8288	Intermediate Similarity	NPC324683
0.8286	Intermediate Similarity	NPC471717
0.8286	Intermediate Similarity	NPC478056
0.8286	Intermediate Similarity	NPC166745
0.8286	Intermediate Similarity	NPC235464
0.8276	Intermediate Similarity	NPC470878
0.8276	Intermediate Similarity	NPC473256
0.8273	Intermediate Similarity	NPC137911
0.8273	Intermediate Similarity	NPC41405
0.8273	Intermediate Similarity	NPC228477
0.8269	Intermediate Similarity	NPC249954
0.8269	Intermediate Similarity	NPC3772
0.8269	Intermediate Similarity	NPC472941
0.8269	Intermediate Similarity	NPC456
0.8269	Intermediate Similarity	NPC471463
0.8261	Intermediate Similarity	NPC473270
0.8257	Intermediate Similarity	NPC144459
0.8246	Intermediate Similarity	NPC239273
0.8246	Intermediate Similarity	NPC243065
0.8241	Intermediate Similarity	NPC118911
0.823	Intermediate Similarity	NPC470953
0.8224	Intermediate Similarity	NPC473163
0.8224	Intermediate Similarity	NPC56498
0.8224	Intermediate Similarity	NPC87351
0.8208	Intermediate Similarity	NPC205899
0.8208	Intermediate Similarity	NPC241221
0.8198	Intermediate Similarity	NPC239097
0.819	Intermediate Similarity	NPC106557
0.819	Intermediate Similarity	NPC107243
0.819	Intermediate Similarity	NPC474343
0.819	Intermediate Similarity	NPC476962
0.819	Intermediate Similarity	NPC202705
0.819	Intermediate Similarity	NPC18319
0.819	Intermediate Similarity	NPC253826
0.8182	Intermediate Similarity	NPC295244
0.8182	Intermediate Similarity	NPC213634
0.8182	Intermediate Similarity	NPC177064
0.8182	Intermediate Similarity	NPC472825
0.8173	Intermediate Similarity	NPC37646
0.8173	Intermediate Similarity	NPC259286
0.8173	Intermediate Similarity	NPC317586
0.8173	Intermediate Similarity	NPC33473
0.8173	Intermediate Similarity	NPC472932
0.8173	Intermediate Similarity	NPC470016
0.8167	Intermediate Similarity	NPC245094
0.8165	Intermediate Similarity	NPC60681
0.8165	Intermediate Similarity	NPC189863
0.8155	Intermediate Similarity	NPC472930
0.8155	Intermediate Similarity	NPC470254
0.8148	Intermediate Similarity	NPC311612
0.8148	Intermediate Similarity	NPC26478
0.8142	Intermediate Similarity	NPC962
0.8142	Intermediate Similarity	NPC472929
0.8137	Intermediate Similarity	NPC477149
0.8137	Intermediate Similarity	NPC477147
0.8137	Intermediate Similarity	NPC273199
0.8131	Intermediate Similarity	NPC472637
0.8125	Intermediate Similarity	NPC179798
0.8125	Intermediate Similarity	NPC304180
0.812	Intermediate Similarity	NPC202051
0.8113	Intermediate Similarity	NPC23364
0.8113	Intermediate Similarity	NPC10364
0.8108	Intermediate Similarity	NPC173905
0.8108	Intermediate Similarity	NPC5475
0.8108	Intermediate Similarity	NPC214644
0.8108	Intermediate Similarity	NPC284828
0.8108	Intermediate Similarity	NPC475065
0.8108	Intermediate Similarity	NPC472216
0.8103	Intermediate Similarity	NPC230513
0.8103	Intermediate Similarity	NPC476960
0.8103	Intermediate Similarity	NPC475520
0.8099	Intermediate Similarity	NPC473593
0.8099	Intermediate Similarity	NPC231529
0.8095	Intermediate Similarity	NPC40765
0.8095	Intermediate Similarity	NPC243525
0.8095	Intermediate Similarity	NPC117133
0.8091	Intermediate Similarity	NPC329048
0.8091	Intermediate Similarity	NPC330011

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 NPC37116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1315
0.2-0.3	3515
0.3-0.4	2675
0.4-0.5	926
0.5-0.6	252
0.6-0.7	190
0.7-0.8	112
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8909	High Similarity	NPD7115	Discovery
0.7895	Intermediate Similarity	NPD8297	Approved
0.7857	Intermediate Similarity	NPD6881	Approved
0.7857	Intermediate Similarity	NPD6899	Approved
0.781	Intermediate Similarity	NPD6399	Phase 3
0.7807	Intermediate Similarity	NPD6650	Approved
0.7807	Intermediate Similarity	NPD6649	Approved
0.7768	Intermediate Similarity	NPD5697	Approved
0.7719	Intermediate Similarity	NPD7102	Approved
0.7719	Intermediate Similarity	NPD6883	Approved
0.7719	Intermediate Similarity	NPD7290	Approved
0.7714	Intermediate Similarity	NPD6079	Approved
0.7699	Intermediate Similarity	NPD6011	Approved
0.7685	Intermediate Similarity	NPD6084	Phase 2
0.7685	Intermediate Similarity	NPD6083	Phase 2
0.7679	Intermediate Similarity	NPD6675	Approved
0.7679	Intermediate Similarity	NPD5739	Approved
0.7679	Intermediate Similarity	NPD6402	Approved
0.7679	Intermediate Similarity	NPD7128	Approved
0.7672	Intermediate Similarity	NPD4632	Approved
0.7664	Intermediate Similarity	NPD5695	Phase 3
0.7652	Intermediate Similarity	NPD6869	Approved
0.7652	Intermediate Similarity	NPD6847	Approved
0.7652	Intermediate Similarity	NPD8130	Phase 1
0.7652	Intermediate Similarity	NPD6617	Approved
0.7632	Intermediate Similarity	NPD6373	Approved
0.7632	Intermediate Similarity	NPD6372	Approved
0.7632	Intermediate Similarity	NPD6012	Approved
0.7632	Intermediate Similarity	NPD6014	Approved
0.7632	Intermediate Similarity	NPD6013	Approved
0.7619	Intermediate Similarity	NPD5785	Approved
0.7615	Intermediate Similarity	NPD4225	Approved
0.7586	Intermediate Similarity	NPD6882	Approved
0.7586	Intermediate Similarity	NPD6053	Discontinued
0.7568	Intermediate Similarity	NPD5211	Phase 2
0.7547	Intermediate Similarity	NPD5284	Approved
0.7547	Intermediate Similarity	NPD5281	Approved
0.7545	Intermediate Similarity	NPD7640	Approved
0.7545	Intermediate Similarity	NPD7639	Approved
0.7544	Intermediate Similarity	NPD7320	Approved
0.7524	Intermediate Similarity	NPD5328	Approved
0.7456	Intermediate Similarity	NPD5701	Approved
0.7455	Intermediate Similarity	NPD7638	Approved
0.7455	Intermediate Similarity	NPD5696	Approved
0.7438	Intermediate Similarity	NPD6319	Approved
0.7434	Intermediate Similarity	NPD5141	Approved
0.7431	Intermediate Similarity	NPD5221	Approved
0.7431	Intermediate Similarity	NPD5222	Approved
0.7431	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5737	Approved
0.7429	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD7507	Approved
0.7404	Intermediate Similarity	NPD7334	Approved
0.7404	Intermediate Similarity	NPD7521	Approved
0.7404	Intermediate Similarity	NPD5330	Approved
0.7404	Intermediate Similarity	NPD7146	Approved
0.7404	Intermediate Similarity	NPD6409	Approved
0.7404	Intermediate Similarity	NPD6684	Approved
0.7391	Intermediate Similarity	NPD6686	Approved
0.7387	Intermediate Similarity	NPD5286	Approved
0.7387	Intermediate Similarity	NPD5285	Approved
0.7387	Intermediate Similarity	NPD4696	Approved
0.7383	Intermediate Similarity	NPD5693	Phase 1
0.7379	Intermediate Similarity	NPD4786	Approved
0.7364	Intermediate Similarity	NPD5173	Approved
0.735	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5210	Approved
0.7339	Intermediate Similarity	NPD4629	Approved
0.7333	Intermediate Similarity	NPD6009	Approved
0.7321	Intermediate Similarity	NPD5223	Approved
0.7308	Intermediate Similarity	NPD1694	Approved
0.7304	Intermediate Similarity	NPD6412	Phase 2
0.729	Intermediate Similarity	NPD5207	Approved
0.7273	Intermediate Similarity	NPD6335	Approved
0.7273	Intermediate Similarity	NPD4697	Phase 3
0.7266	Intermediate Similarity	NPD7260	Phase 2
0.7265	Intermediate Similarity	NPD6371	Approved
0.7264	Intermediate Similarity	NPD6903	Approved
0.7258	Intermediate Similarity	NPD7604	Phase 2
0.7257	Intermediate Similarity	NPD5225	Approved
0.7257	Intermediate Similarity	NPD4633	Approved
0.7257	Intermediate Similarity	NPD5226	Approved
0.7257	Intermediate Similarity	NPD5224	Approved
0.725	Intermediate Similarity	NPD6868	Approved
0.7248	Intermediate Similarity	NPD7748	Approved
0.7244	Intermediate Similarity	NPD7319	Approved
0.7238	Intermediate Similarity	NPD5279	Phase 3
0.7238	Intermediate Similarity	NPD3618	Phase 1
0.7238	Intermediate Similarity	NPD5690	Phase 2
0.7236	Intermediate Similarity	NPD5983	Phase 2
0.7236	Intermediate Similarity	NPD7503	Approved
0.7222	Intermediate Similarity	NPD6411	Approved
0.7222	Intermediate Similarity	NPD5694	Approved
0.7222	Intermediate Similarity	NPD6050	Approved
0.7222	Intermediate Similarity	NPD7515	Phase 2
0.7217	Intermediate Similarity	NPD6008	Approved
0.7213	Intermediate Similarity	NPD7100	Approved
0.7213	Intermediate Similarity	NPD7101	Approved
0.7212	Intermediate Similarity	NPD3665	Phase 1
0.7212	Intermediate Similarity	NPD3666	Approved
0.7212	Intermediate Similarity	NPD3133	Approved
0.7207	Intermediate Similarity	NPD7902	Approved
0.7207	Intermediate Similarity	NPD4755	Approved
0.72	Intermediate Similarity	NPD7492	Approved
0.7196	Intermediate Similarity	NPD6904	Approved
0.7196	Intermediate Similarity	NPD6673	Approved
0.7196	Intermediate Similarity	NPD4753	Phase 2
0.7196	Intermediate Similarity	NPD6080	Approved
0.7193	Intermediate Similarity	NPD5175	Approved
0.7193	Intermediate Similarity	NPD5174	Approved
0.719	Intermediate Similarity	NPD6317	Approved
0.7184	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3667	Approved
0.7182	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3573	Approved
0.7165	Intermediate Similarity	NPD7736	Approved
0.7156	Intermediate Similarity	NPD5779	Approved
0.7156	Intermediate Similarity	NPD5778	Approved
0.7154	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD5363	Approved
0.7143	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD6616	Approved
0.7131	Intermediate Similarity	NPD6314	Approved
0.7131	Intermediate Similarity	NPD6313	Approved
0.713	Intermediate Similarity	NPD5692	Phase 3
0.7129	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4634	Approved
0.7107	Intermediate Similarity	NPD6274	Approved
0.7097	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7078	Approved
0.708	Intermediate Similarity	NPD4700	Approved
0.7075	Intermediate Similarity	NPD5786	Approved
0.704	Intermediate Similarity	NPD6370	Approved
0.7037	Intermediate Similarity	NPD6101	Approved
0.7037	Intermediate Similarity	NPD6051	Approved
0.7037	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4223	Phase 3
0.7019	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD4202	Approved
0.6981	Remote Similarity	NPD5329	Approved
0.696	Remote Similarity	NPD6015	Approved
0.696	Remote Similarity	NPD8513	Phase 3
0.696	Remote Similarity	NPD6016	Approved
0.6957	Remote Similarity	NPD7632	Discontinued
0.6952	Remote Similarity	NPD5362	Discontinued
0.6949	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD4729	Approved
0.6949	Remote Similarity	NPD4730	Approved
0.6944	Remote Similarity	NPD5208	Approved
0.6937	Remote Similarity	NPD7900	Approved
0.6937	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6404	Discontinued
0.6917	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4519	Discontinued
0.6916	Remote Similarity	NPD5280	Approved
0.6916	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4694	Approved
0.6916	Remote Similarity	NPD6098	Approved
0.6916	Remote Similarity	NPD4623	Approved
0.6909	Remote Similarity	NPD7637	Suspended
0.6909	Remote Similarity	NPD8035	Phase 2
0.6909	Remote Similarity	NPD8034	Phase 2
0.6905	Remote Similarity	NPD5988	Approved
0.6897	Remote Similarity	NPD4754	Approved
0.6887	Remote Similarity	NPD4197	Approved
0.6881	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6059	Approved
0.6857	Remote Similarity	NPD4270	Approved
0.6857	Remote Similarity	NPD4269	Approved
0.6855	Remote Similarity	NPD7327	Approved
0.6855	Remote Similarity	NPD7328	Approved
0.6833	Remote Similarity	NPD5250	Approved
0.6833	Remote Similarity	NPD5249	Phase 3
0.6833	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5251	Approved
0.6833	Remote Similarity	NPD5169	Approved
0.6833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5247	Approved
0.6833	Remote Similarity	NPD5135	Approved
0.6833	Remote Similarity	NPD5248	Approved
0.6825	Remote Similarity	NPD8515	Approved
0.6825	Remote Similarity	NPD8033	Approved
0.6825	Remote Similarity	NPD8517	Approved
0.6825	Remote Similarity	NPD8516	Approved
0.6825	Remote Similarity	NPD6909	Approved
0.6825	Remote Similarity	NPD6908	Approved
0.6822	Remote Similarity	NPD8293	Discontinued
0.6822	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6698	Approved
0.6818	Remote Similarity	NPD6845	Suspended
0.6818	Remote Similarity	NPD46	Approved
0.6807	Remote Similarity	NPD5168	Approved
0.6807	Remote Similarity	NPD5128	Approved
0.68	Remote Similarity	NPD7516	Approved
0.6792	Remote Similarity	NPD4788	Approved
0.6786	Remote Similarity	NPD6001	Approved
0.678	Remote Similarity	NPD4768	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