NPASS Compound

Structure

NPC476223 OpenBabel07101718302D 34 36 0 0 1 0 0 0 0 0999 V2000 -4.5428 4.2815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9386 3.1589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5820 -0.1817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2100 -3.0872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -0.6499 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 -5.5374 4.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3563 2.4544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7631 1.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 -0.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8717 -1.6009 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9441 3.2635 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1753 0.7319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2318 -3.2951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 0.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9228 -4.2462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5627 -2.5520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 7 18 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 34 1 0 0 0 0 16 21 1 0 0 0 0 16 25 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 20 30 2 0 0 0 0 20 34 1 0 0 0 0 21 31 1 6 0 0 0 22 24 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 1 0 0 0 24 28 1 1 0 0 0 25 26 1 0 0 0 0 25 29 1 6 0 0 0 26 32 1 1 0 0 0 27 29 1 0 0 0 0 27 33 2 0 0 0 0 28 5 1 1 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.33
Volume:	517.876
LogP:	4.376
LogD:	4.902
LogS:	-5.203
# Rotatable Bonds:	9
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	5.017
Fsp3:	0.828
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:	-4.747
MDCK Permeability:	3.127887976006605e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.635
Human Intestinal Absorption (HIA):	0.378
20% Bioavailability (F20%):	0.825
30% Bioavailability (F30%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	85.82209777832031%
Volume Distribution (VD):	0.971
Pgp-substrate:	1.5574214458465576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.337
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.102
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.765

ADMET: Excretion

Clearance (CL):	5.867
Half-life (T1/2):	0.233

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.559
Drug-inuced Liver Injury (DILI):	0.32
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.829
Skin Sensitization:	0.067
Carcinogencity:	0.028
Eye Corrosion:	0.006
Eye Irritation:	0.02
Respiratory Toxicity:	0.498

Download Data

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

Natural Product: NPC476223

Natural Product ID:	NPC476223
*Common Name:**	(22E)-11-Acetoxy-3B,6A-Dihydroxy-24N-Methyl-27-Nor-9,11-Seco-5A-Cholesta-7,22-Dien-9-One
IUPAC Name:	2-[(1R,2R,5R)-2-[(4S,4aS,6S,8aS)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(E,2R)-5-methylhept-3-en-2-yl]cyclopentyl]ethyl acetate
Synonyms:
Standard InCHIKey:	UQSMZCYYNIALNN-OSJJDKCPSA-N
Standard InCHI:	InChI=1S/C29H46O5/c1-7-18(2)8-9-19(3)23-10-11-24(28(23,5)14-15-34-20(4)30)22-17-26(32)25-16-21(31)12-13-29(25,6)27(22)33/h8-9,17-19,21,23-26,31-32H,7,10-16H2,1-6H3/b9-8+/t18?,19-,21+,23-,24+,25-,26+,28-,29+/m1/s1
SMILES:	CCC(C)C=CC(C)C1CCC(C1(C)CCOC(=O)C)C2=CC(C3CC(CCC3(C2=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555868
PubChem CID:	44241584
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO33183	eunicella cavolini	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19467602]

☑ 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	3
Others	3

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	GI	=	83.0	%	PMID[506165]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	5400.0	nM	PMID[506165]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	49.0	%	PMID[506165]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7000.0	nM	PMID[506165]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	90.0	%	PMID[506165]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5400.0	nM	PMID[506165]

☑ 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 NPC476223 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	170
0.1-0.2	973
0.2-0.3	3969
0.3-0.4	8291
0.4-0.5	13146
0.5-0.6	6812
0.6-0.7	6223
0.7-0.8	2751
0.8-0.85	301
0.85-0.9	55
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224720
1.0	High Similarity	NPC476240
0.9892	High Similarity	NPC476274
0.9278	High Similarity	NPC136289
0.9175	High Similarity	NPC81530
0.8878	High Similarity	NPC287833
0.88	High Similarity	NPC236390
0.8776	High Similarity	NPC197386
0.8763	High Similarity	NPC249954
0.8763	High Similarity	NPC301534
0.8763	High Similarity	NPC250757
0.8763	High Similarity	NPC328371
0.875	High Similarity	NPC184870
0.8725	High Similarity	NPC475294
0.8713	High Similarity	NPC118911
0.87	High Similarity	NPC119601
0.87	High Similarity	NPC204450
0.87	High Similarity	NPC308726
0.87	High Similarity	NPC195290
0.87	High Similarity	NPC293753
0.8687	High Similarity	NPC51370
0.8687	High Similarity	NPC266955
0.8673	High Similarity	NPC253826
0.8673	High Similarity	NPC474343
0.8673	High Similarity	NPC121339
0.8673	High Similarity	NPC107243
0.866	High Similarity	NPC173875
0.866	High Similarity	NPC259286
0.866	High Similarity	NPC174948
0.866	High Similarity	NPC470016
0.866	High Similarity	NPC469995
0.866	High Similarity	NPC318282
0.866	High Similarity	NPC317586
0.8654	High Similarity	NPC37116
0.8646	High Similarity	NPC69454
0.8641	High Similarity	NPC295244
0.8632	High Similarity	NPC477147
0.8632	High Similarity	NPC477149
0.86	High Similarity	NPC302537
0.86	High Similarity	NPC472924
0.86	High Similarity	NPC115899
0.86	High Similarity	NPC115862
0.86	High Similarity	NPC163372
0.8586	High Similarity	NPC478056
0.8586	High Similarity	NPC108368
0.8586	High Similarity	NPC57079
0.8586	High Similarity	NPC114274
0.8585	High Similarity	NPC250109
0.8585	High Similarity	NPC472929
0.8585	High Similarity	NPC962
0.8571	High Similarity	NPC7124
0.8571	High Similarity	NPC3772
0.8571	High Similarity	NPC474315
0.8571	High Similarity	NPC472941
0.8571	High Similarity	NPC456
0.8558	High Similarity	NPC474901
0.8558	High Similarity	NPC475941
0.8557	High Similarity	NPC166906
0.8557	High Similarity	NPC8993
0.8544	High Similarity	NPC44063
0.8544	High Similarity	NPC472925
0.8544	High Similarity	NPC91034
0.8542	High Similarity	NPC475806
0.8542	High Similarity	NPC63748
0.8542	High Similarity	NPC473998
0.8529	High Similarity	NPC255309
0.8529	High Similarity	NPC235889
0.8529	High Similarity	NPC28656
0.8526	High Similarity	NPC473999
0.8526	High Similarity	NPC123912
0.8526	High Similarity	NPC214387
0.8526	High Similarity	NPC309603
0.8519	High Similarity	NPC471854
0.8515	High Similarity	NPC234892
0.8515	High Similarity	NPC56498
0.85	High Similarity	NPC218383
0.85	High Similarity	NPC477521
0.85	High Similarity	NPC205899
0.85	High Similarity	NPC112167
0.85	High Similarity	NPC307954
0.85	High Similarity	NPC241221
0.8491	Intermediate Similarity	NPC100267
0.8491	Intermediate Similarity	NPC264634
0.8491	Intermediate Similarity	NPC475524
0.8491	Intermediate Similarity	NPC71348
0.8491	Intermediate Similarity	NPC475970
0.8485	Intermediate Similarity	NPC320306
0.8485	Intermediate Similarity	NPC106557
0.8485	Intermediate Similarity	NPC108078
0.8485	Intermediate Similarity	NPC57416
0.8485	Intermediate Similarity	NPC18319
0.8485	Intermediate Similarity	NPC475894
0.8485	Intermediate Similarity	NPC170131
0.8476	Intermediate Similarity	NPC197428
0.8469	Intermediate Similarity	NPC469599
0.8469	Intermediate Similarity	NPC476174
0.8469	Intermediate Similarity	NPC134067
0.8469	Intermediate Similarity	NPC37646
0.8462	Intermediate Similarity	NPC469844
0.8454	Intermediate Similarity	NPC476416
0.8454	Intermediate Similarity	NPC38232
0.8454	Intermediate Similarity	NPC470254
0.8454	Intermediate Similarity	NPC472930
0.8447	Intermediate Similarity	NPC323834
0.8447	Intermediate Similarity	NPC96377
0.8447	Intermediate Similarity	NPC181265
0.8431	Intermediate Similarity	NPC311612
0.8431	Intermediate Similarity	NPC72151
0.8431	Intermediate Similarity	NPC264048
0.8431	Intermediate Similarity	NPC55872
0.8431	Intermediate Similarity	NPC476237
0.8426	Intermediate Similarity	NPC148458
0.8426	Intermediate Similarity	NPC270929
0.8426	Intermediate Similarity	NPC266728
0.8426	Intermediate Similarity	NPC49492
0.8416	Intermediate Similarity	NPC99411
0.8416	Intermediate Similarity	NPC282524
0.8416	Intermediate Similarity	NPC474327
0.8411	Intermediate Similarity	NPC122056
0.8411	Intermediate Similarity	NPC472926
0.84	Intermediate Similarity	NPC103051
0.84	Intermediate Similarity	NPC235464
0.84	Intermediate Similarity	NPC166745
0.84	Intermediate Similarity	NPC471717
0.84	Intermediate Similarity	NPC10364
0.84	Intermediate Similarity	NPC48647
0.84	Intermediate Similarity	NPC222011
0.8396	Intermediate Similarity	NPC472928
0.8387	Intermediate Similarity	NPC165064
0.8387	Intermediate Similarity	NPC164577
0.8384	Intermediate Similarity	NPC305483
0.8384	Intermediate Similarity	NPC328162
0.8384	Intermediate Similarity	NPC96859
0.8384	Intermediate Similarity	NPC40765
0.8384	Intermediate Similarity	NPC243525
0.8381	Intermediate Similarity	NPC258543
0.8381	Intermediate Similarity	NPC2766
0.8381	Intermediate Similarity	NPC241927
0.8367	Intermediate Similarity	NPC299100
0.8367	Intermediate Similarity	NPC469406
0.8365	Intermediate Similarity	NPC473037
0.8364	Intermediate Similarity	NPC61520
0.8351	Intermediate Similarity	NPC470113
0.8351	Intermediate Similarity	NPC107690
0.8351	Intermediate Similarity	NPC252433
0.8351	Intermediate Similarity	NPC474018
0.8351	Intermediate Similarity	NPC154101
0.8351	Intermediate Similarity	NPC297265
0.8351	Intermediate Similarity	NPC473986
0.8351	Intermediate Similarity	NPC218301
0.835	Intermediate Similarity	NPC189616
0.835	Intermediate Similarity	NPC96268
0.8349	Intermediate Similarity	NPC472934
0.8349	Intermediate Similarity	NPC472927
0.8333	Intermediate Similarity	NPC66344
0.8333	Intermediate Similarity	NPC310236
0.8333	Intermediate Similarity	NPC262858
0.8333	Intermediate Similarity	NPC86319
0.8333	Intermediate Similarity	NPC281702
0.8333	Intermediate Similarity	NPC114540
0.8333	Intermediate Similarity	NPC474181
0.8333	Intermediate Similarity	NPC275740
0.8333	Intermediate Similarity	NPC473424
0.8333	Intermediate Similarity	NPC67259
0.8333	Intermediate Similarity	NPC472983
0.8333	Intermediate Similarity	NPC262043
0.8333	Intermediate Similarity	NPC5509
0.8333	Intermediate Similarity	NPC320447
0.8333	Intermediate Similarity	NPC477915
0.8333	Intermediate Similarity	NPC147912
0.8333	Intermediate Similarity	NPC155332
0.8333	Intermediate Similarity	NPC32577
0.8333	Intermediate Similarity	NPC87351
0.8333	Intermediate Similarity	NPC472240
0.8318	Intermediate Similarity	NPC236217
0.8318	Intermediate Similarity	NPC147180
0.8318	Intermediate Similarity	NPC221144
0.8317	Intermediate Similarity	NPC316964
0.8317	Intermediate Similarity	NPC472644
0.8317	Intermediate Similarity	NPC154072
0.8317	Intermediate Similarity	NPC470074
0.8317	Intermediate Similarity	NPC201406
0.8317	Intermediate Similarity	NPC299971
0.8317	Intermediate Similarity	NPC471041
0.8317	Intermediate Similarity	NPC144660
0.8317	Intermediate Similarity	NPC327431
0.8316	Intermediate Similarity	NPC167877
0.8302	Intermediate Similarity	NPC473627
0.8302	Intermediate Similarity	NPC272898
0.8302	Intermediate Similarity	NPC239097
0.8302	Intermediate Similarity	NPC473036
0.83	Intermediate Similarity	NPC141401
0.83	Intermediate Similarity	NPC43747
0.83	Intermediate Similarity	NPC122294
0.83	Intermediate Similarity	NPC226986
0.83	Intermediate Similarity	NPC292133
0.83	Intermediate Similarity	NPC254496
0.83	Intermediate Similarity	NPC23680
0.83	Intermediate Similarity	NPC69385
0.8288	Intermediate Similarity	NPC476962

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 NPC476223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1293
0.2-0.3	3583
0.3-0.4	2647
0.4-0.5	919
0.5-0.6	235
0.6-0.7	173
0.7-0.8	131
0.8-0.85	26
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8641	High Similarity	NPD6881	Approved
0.8641	High Similarity	NPD6899	Approved
0.8571	High Similarity	NPD6649	Approved
0.8571	High Similarity	NPD6650	Approved
0.8544	High Similarity	NPD5697	Approved
0.8542	High Similarity	NPD6079	Approved
0.8476	Intermediate Similarity	NPD6883	Approved
0.8476	Intermediate Similarity	NPD7290	Approved
0.8476	Intermediate Similarity	NPD7102	Approved
0.8462	Intermediate Similarity	NPD6011	Approved
0.8454	Intermediate Similarity	NPD6399	Phase 3
0.8447	Intermediate Similarity	NPD6402	Approved
0.8447	Intermediate Similarity	NPD5739	Approved
0.8447	Intermediate Similarity	NPD6675	Approved
0.8447	Intermediate Similarity	NPD7128	Approved
0.8396	Intermediate Similarity	NPD6847	Approved
0.8396	Intermediate Similarity	NPD6869	Approved
0.8396	Intermediate Similarity	NPD6617	Approved
0.8396	Intermediate Similarity	NPD8130	Phase 1
0.8381	Intermediate Similarity	NPD6013	Approved
0.8381	Intermediate Similarity	NPD6012	Approved
0.8381	Intermediate Similarity	NPD6372	Approved
0.8381	Intermediate Similarity	NPD6014	Approved
0.8381	Intermediate Similarity	NPD6373	Approved
0.8333	Intermediate Similarity	NPD5328	Approved
0.8333	Intermediate Similarity	NPD5211	Phase 2
0.8318	Intermediate Similarity	NPD8297	Approved
0.8318	Intermediate Similarity	NPD6882	Approved
0.8286	Intermediate Similarity	NPD7320	Approved
0.82	Intermediate Similarity	NPD5222	Approved
0.82	Intermediate Similarity	NPD5221	Approved
0.82	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD5701	Approved
0.8182	Intermediate Similarity	NPD7115	Discovery
0.8173	Intermediate Similarity	NPD5141	Approved
0.8137	Intermediate Similarity	NPD5286	Approved
0.8137	Intermediate Similarity	NPD4696	Approved
0.8137	Intermediate Similarity	NPD5285	Approved
0.8119	Intermediate Similarity	NPD5173	Approved
0.8058	Intermediate Similarity	NPD5223	Approved
0.8056	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD3618	Phase 1
0.802	Intermediate Similarity	NPD4697	Phase 3
0.7981	Intermediate Similarity	NPD5224	Approved
0.7981	Intermediate Similarity	NPD5226	Approved
0.7981	Intermediate Similarity	NPD4633	Approved
0.7981	Intermediate Similarity	NPD5225	Approved
0.7961	Intermediate Similarity	NPD7640	Approved
0.7961	Intermediate Similarity	NPD7639	Approved
0.7946	Intermediate Similarity	NPD6335	Approved
0.7941	Intermediate Similarity	NPD6084	Phase 2
0.7941	Intermediate Similarity	NPD6083	Phase 2
0.7941	Intermediate Similarity	NPD4755	Approved
0.7941	Intermediate Similarity	NPD7902	Approved
0.7928	Intermediate Similarity	NPD6868	Approved
0.7909	Intermediate Similarity	NPD4632	Approved
0.7905	Intermediate Similarity	NPD5175	Approved
0.7905	Intermediate Similarity	NPD5174	Approved
0.7876	Intermediate Similarity	NPD7100	Approved
0.7876	Intermediate Similarity	NPD7101	Approved
0.7864	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD6672	Approved
0.7857	Intermediate Similarity	NPD5737	Approved
0.7857	Intermediate Similarity	NPD6317	Approved
0.7835	Intermediate Similarity	NPD5330	Approved
0.7835	Intermediate Similarity	NPD6684	Approved
0.7835	Intermediate Similarity	NPD7334	Approved
0.7835	Intermediate Similarity	NPD7521	Approved
0.7835	Intermediate Similarity	NPD6409	Approved
0.7835	Intermediate Similarity	NPD7146	Approved
0.7822	Intermediate Similarity	NPD7748	Approved
0.7812	Intermediate Similarity	NPD4786	Approved
0.78	Intermediate Similarity	NPD7515	Phase 2
0.78	Intermediate Similarity	NPD5281	Approved
0.78	Intermediate Similarity	NPD5284	Approved
0.7788	Intermediate Similarity	NPD4700	Approved
0.7788	Intermediate Similarity	NPD6314	Approved
0.7788	Intermediate Similarity	NPD6313	Approved
0.7768	Intermediate Similarity	NPD6274	Approved
0.7757	Intermediate Similarity	NPD6008	Approved
0.7745	Intermediate Similarity	NPD5695	Phase 3
0.7742	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD1694	Approved
0.7723	Intermediate Similarity	NPD4202	Approved
0.77	Intermediate Similarity	NPD5785	Approved
0.7699	Intermediate Similarity	NPD6009	Approved
0.7692	Intermediate Similarity	NPD5696	Approved
0.7677	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6903	Approved
0.7652	Intermediate Similarity	NPD6319	Approved
0.7647	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7900	Approved
0.7629	Intermediate Similarity	NPD3666	Approved
0.7629	Intermediate Similarity	NPD3133	Approved
0.7629	Intermediate Similarity	NPD3665	Phase 1
0.7624	Intermediate Similarity	NPD8034	Phase 2
0.7624	Intermediate Similarity	NPD8035	Phase 2
0.7615	Intermediate Similarity	NPD4729	Approved
0.7615	Intermediate Similarity	NPD4730	Approved
0.7607	Intermediate Similarity	NPD7604	Phase 2
0.7604	Intermediate Similarity	NPD3667	Approved
0.7586	Intermediate Similarity	NPD5983	Phase 2
0.7576	Intermediate Similarity	NPD3573	Approved
0.7573	Intermediate Similarity	NPD5210	Approved
0.7573	Intermediate Similarity	NPD4629	Approved
0.7573	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD4754	Approved
0.7551	Intermediate Similarity	NPD5363	Approved
0.7549	Intermediate Similarity	NPD5778	Approved
0.7549	Intermediate Similarity	NPD5779	Approved
0.7542	Intermediate Similarity	NPD7492	Approved
0.7524	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.7479	Intermediate Similarity	NPD6336	Discontinued
0.7479	Intermediate Similarity	NPD6616	Approved
0.7477	Intermediate Similarity	NPD5249	Phase 3
0.7477	Intermediate Similarity	NPD5248	Approved
0.7477	Intermediate Similarity	NPD5135	Approved
0.7477	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD5169	Approved
0.7477	Intermediate Similarity	NPD5250	Approved
0.7477	Intermediate Similarity	NPD5251	Approved
0.7477	Intermediate Similarity	NPD4634	Approved
0.7477	Intermediate Similarity	NPD5247	Approved
0.7475	Intermediate Similarity	NPD5279	Phase 3
0.7475	Intermediate Similarity	NPD5786	Approved
0.7455	Intermediate Similarity	NPD5128	Approved
0.7455	Intermediate Similarity	NPD5168	Approved
0.7451	Intermediate Similarity	NPD6411	Approved
0.7436	Intermediate Similarity	NPD6909	Approved
0.7436	Intermediate Similarity	NPD6908	Approved
0.7431	Intermediate Similarity	NPD4768	Approved
0.7431	Intermediate Similarity	NPD4767	Approved
0.7426	Intermediate Similarity	NPD4753	Phase 2
0.7426	Intermediate Similarity	NPD6904	Approved
0.7426	Intermediate Similarity	NPD6673	Approved
0.7426	Intermediate Similarity	NPD6080	Approved
0.7423	Intermediate Similarity	NPD6435	Approved
0.7423	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7078	Approved
0.7411	Intermediate Similarity	NPD5217	Approved
0.7411	Intermediate Similarity	NPD5215	Approved
0.7411	Intermediate Similarity	NPD5127	Approved
0.7411	Intermediate Similarity	NPD5216	Approved
0.7404	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6370	Approved
0.7355	Intermediate Similarity	NPD7736	Approved
0.7353	Intermediate Similarity	NPD5207	Approved
0.7347	Intermediate Similarity	NPD5362	Discontinued
0.7345	Intermediate Similarity	NPD6053	Discontinued
0.7315	Intermediate Similarity	NPD7632	Discontinued
0.73	Intermediate Similarity	NPD5690	Phase 2
0.73	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6016	Approved
0.7288	Intermediate Similarity	NPD6015	Approved
0.7282	Intermediate Similarity	NPD7637	Suspended
0.7282	Intermediate Similarity	NPD5694	Approved
0.7282	Intermediate Similarity	NPD5693	Phase 1
0.7282	Intermediate Similarity	NPD6050	Approved
0.7255	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6101	Approved
0.7245	Intermediate Similarity	NPD4270	Approved
0.7245	Intermediate Similarity	NPD4269	Approved
0.7245	Intermediate Similarity	NPD4221	Approved
0.7245	Intermediate Similarity	NPD4223	Phase 3
0.7227	Intermediate Similarity	NPD5988	Approved
0.7217	Intermediate Similarity	NPD5167	Approved
0.7216	Intermediate Similarity	NPD5368	Approved
0.7207	Intermediate Similarity	NPD6412	Phase 2
0.7203	Intermediate Similarity	NPD6059	Approved
0.72	Intermediate Similarity	NPD5329	Approved
0.719	Intermediate Similarity	NPD7507	Approved
0.7184	Intermediate Similarity	NPD5692	Phase 3
0.7157	Intermediate Similarity	NPD5208	Approved
0.7143	Intermediate Similarity	NPD6001	Approved
0.7143	Intermediate Similarity	NPD6686	Approved
0.7131	Intermediate Similarity	NPD8293	Discontinued
0.713	Intermediate Similarity	NPD6404	Discontinued
0.7129	Intermediate Similarity	NPD6098	Approved
0.7129	Intermediate Similarity	NPD4623	Approved
0.7129	Intermediate Similarity	NPD4519	Discontinued
0.71	Intermediate Similarity	NPD4197	Approved
0.71	Intermediate Similarity	NPD3668	Phase 3
0.7041	Intermediate Similarity	NPD4252	Approved
0.7041	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7525	Registered
0.7016	Intermediate Similarity	NPD7319	Approved
0.7	Intermediate Similarity	NPD4788	Approved
0.7	Intermediate Similarity	NPD7154	Phase 3
0.697	Remote Similarity	NPD5369	Approved
0.6961	Remote Similarity	NPD5205	Approved
0.6961	Remote Similarity	NPD4688	Approved
0.6961	Remote Similarity	NPD5280	Approved
0.6961	Remote Similarity	NPD4138	Approved
0.6961	Remote Similarity	NPD4693	Phase 3
0.6961	Remote Similarity	NPD4694	Approved
0.6961	Remote Similarity	NPD4690	Approved
0.6961	Remote Similarity	NPD4689	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