NPASS Compound

Structure

NPC476274 OpenBabel07101718332D 35 37 0 0 1 0 0 0 0 0999 V2000 7.3454 -2.2454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5264 -3.9679 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 5.5820 0.1817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9228 4.2462 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 5.3563 -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 6.9386 -3.1589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9441 -3.2635 0.0000 C 0 0 0 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 5.2100 3.0872 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 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 5 21 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 29 1 0 0 0 0 15 35 1 0 0 0 0 16 22 1 0 0 0 0 16 26 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 20 4 1 6 0 0 0 20 24 1 0 0 0 0 21 31 2 0 0 0 0 21 35 1 0 0 0 0 22 32 1 6 0 0 0 23 25 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 1 0 0 0 25 29 1 1 0 0 0 26 27 1 0 0 0 0 26 30 1 6 0 0 0 27 33 1 1 0 0 0 28 30 1 0 0 0 0 28 34 2 0 0 0 0 29 6 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	535.172
LogP:	4.514
LogD:	5.035
LogS:	-5.075
# Rotatable Bonds:	10
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	4.895
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.769
MDCK Permeability:	2.329035305592697e-05
Pgp-inhibitor:	0.758
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.807
30% Bioavailability (F30%):	0.584

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.497
Plasma Protein Binding (PPB):	90.71953582763672%
Volume Distribution (VD):	0.858
Pgp-substrate:	5.13596773147583%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.297
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.262
CYP2C9-substrate:	0.143
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.729

ADMET: Excretion

Clearance (CL):	8.21
Half-life (T1/2):	0.197

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.449
Drug-inuced Liver Injury (DILI):	0.618
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.351
Skin Sensitization:	0.04
Carcinogencity:	0.112
Eye Corrosion:	0.046
Eye Irritation:	0.051
Respiratory Toxicity:	0.77

Download Data

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

Natural Product: NPC476274

Natural Product ID:	NPC476274
*Common Name:**	11-Acetoxy-3B,6A-Dihydroxy-24-Methyl-9,11-Seco-5Acholesta-7,24(28)-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-[(2R)-6-methyl-5-methylideneheptan-2-yl]cyclopentyl]ethyl acetate
Synonyms:
Standard InCHIKey:	OXUORJYMAXIVJG-QWJARAQCSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-18(2)19(3)8-9-20(4)24-10-11-25(29(24,6)14-15-35-21(5)31)23-17-27(33)26-16-22(32)12-13-30(26,7)28(23)34/h17-18,20,22,24-27,32-33H,3,8-16H2,1-2,4-7H3/t20-,22+,24-,25+,26-,27+,29-,30+/m1/s1
SMILES:	CC(C)C(=C)CCC(C)C1CCC(C1(C)CCOC(=O)C)C2=CC(C3CC(CCC3(C2=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560722
PubChem CID:	45268228
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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	1
Others	3

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	GI	<=	10.0	%	PMID[452144]
NPT83	Cell Line	MCF7	Homo sapiens	GI	<=	10.0	%	PMID[452144]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	50.0	%	PMID[452144]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3800.0	nM	PMID[452144]

☑ 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 NPC476274 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	168
0.1-0.2	1037
0.2-0.3	4122
0.3-0.4	8599
0.4-0.5	12803
0.5-0.6	6424
0.6-0.7	6325
0.7-0.8	2795
0.8-0.85	344
0.85-0.9	69
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC476240
0.9892	High Similarity	NPC224720
0.9892	High Similarity	NPC476223
0.9375	High Similarity	NPC136289
0.9271	High Similarity	NPC81530
0.8969	High Similarity	NPC287833
0.8889	High Similarity	NPC236390
0.8866	High Similarity	NPC197386
0.8854	High Similarity	NPC328371
0.8842	High Similarity	NPC184870
0.8788	High Similarity	NPC195290
0.8788	High Similarity	NPC119601
0.8788	High Similarity	NPC308726
0.8788	High Similarity	NPC204450
0.8788	High Similarity	NPC293753
0.8776	High Similarity	NPC51370
0.8763	High Similarity	NPC474343
0.8763	High Similarity	NPC121339
0.8763	High Similarity	NPC253826
0.875	High Similarity	NPC469995
0.875	High Similarity	NPC318282
0.875	High Similarity	NPC317586
0.875	High Similarity	NPC173875
0.875	High Similarity	NPC174948
0.875	High Similarity	NPC470016
0.8737	High Similarity	NPC69454
0.8725	High Similarity	NPC295244
0.8723	High Similarity	NPC477147
0.8723	High Similarity	NPC477149
0.8687	High Similarity	NPC472924
0.8687	High Similarity	NPC163372
0.8687	High Similarity	NPC302537
0.8673	High Similarity	NPC478056
0.8667	High Similarity	NPC472929
0.8667	High Similarity	NPC962
0.8667	High Similarity	NPC250109
0.866	High Similarity	NPC7124
0.866	High Similarity	NPC249954
0.866	High Similarity	NPC250757
0.866	High Similarity	NPC456
0.866	High Similarity	NPC3772
0.866	High Similarity	NPC301534
0.866	High Similarity	NPC472941
0.8646	High Similarity	NPC166906
0.8641	High Similarity	NPC475941
0.8641	High Similarity	NPC474901
0.8632	High Similarity	NPC473998
0.8632	High Similarity	NPC63748
0.8627	High Similarity	NPC475294
0.8627	High Similarity	NPC472925
0.8617	High Similarity	NPC214387
0.8617	High Similarity	NPC123912
0.8617	High Similarity	NPC473999
0.8617	High Similarity	NPC309603
0.8614	High Similarity	NPC118911
0.8614	High Similarity	NPC28656
0.86	High Similarity	NPC234892
0.86	High Similarity	NPC56498
0.8586	High Similarity	NPC241221
0.8586	High Similarity	NPC307954
0.8586	High Similarity	NPC205899
0.8586	High Similarity	NPC266955
0.8586	High Similarity	NPC218383
0.8586	High Similarity	NPC477521
0.8571	High Similarity	NPC320306
0.8571	High Similarity	NPC170131
0.8571	High Similarity	NPC106557
0.8571	High Similarity	NPC107243
0.8571	High Similarity	NPC475894
0.8571	High Similarity	NPC18319
0.8558	High Similarity	NPC37116
0.8557	High Similarity	NPC37646
0.8557	High Similarity	NPC259286
0.8557	High Similarity	NPC134067
0.8557	High Similarity	NPC476174
0.8557	High Similarity	NPC469599
0.8542	High Similarity	NPC470254
0.8542	High Similarity	NPC472930
0.8542	High Similarity	NPC476416
0.8542	High Similarity	NPC38232
0.8529	High Similarity	NPC323834
0.8515	High Similarity	NPC55872
0.8515	High Similarity	NPC476237
0.8505	High Similarity	NPC49492
0.8505	High Similarity	NPC266728
0.85	High Similarity	NPC115899
0.85	High Similarity	NPC474327
0.85	High Similarity	NPC115862
0.85	High Similarity	NPC99411
0.8491	Intermediate Similarity	NPC472926
0.8485	Intermediate Similarity	NPC10364
0.8485	Intermediate Similarity	NPC235464
0.8485	Intermediate Similarity	NPC222011
0.8485	Intermediate Similarity	NPC471717
0.8485	Intermediate Similarity	NPC166745
0.8485	Intermediate Similarity	NPC48647
0.8485	Intermediate Similarity	NPC108368
0.8485	Intermediate Similarity	NPC114274
0.8485	Intermediate Similarity	NPC57079
0.8478	Intermediate Similarity	NPC164577
0.8478	Intermediate Similarity	NPC165064
0.8476	Intermediate Similarity	NPC474315
0.8476	Intermediate Similarity	NPC472928
0.8469	Intermediate Similarity	NPC328162
0.8469	Intermediate Similarity	NPC40765
0.8469	Intermediate Similarity	NPC96859
0.8469	Intermediate Similarity	NPC243525
0.8469	Intermediate Similarity	NPC305483
0.8454	Intermediate Similarity	NPC469406
0.8454	Intermediate Similarity	NPC8993
0.8447	Intermediate Similarity	NPC91034
0.8447	Intermediate Similarity	NPC473037
0.8447	Intermediate Similarity	NPC44063
0.8438	Intermediate Similarity	NPC470113
0.8438	Intermediate Similarity	NPC154101
0.8438	Intermediate Similarity	NPC107690
0.8438	Intermediate Similarity	NPC475806
0.8438	Intermediate Similarity	NPC297265
0.8431	Intermediate Similarity	NPC96268
0.8431	Intermediate Similarity	NPC235889
0.8431	Intermediate Similarity	NPC255309
0.8426	Intermediate Similarity	NPC472934
0.8426	Intermediate Similarity	NPC472927
0.8426	Intermediate Similarity	NPC471854
0.8421	Intermediate Similarity	NPC262858
0.8421	Intermediate Similarity	NPC472240
0.8421	Intermediate Similarity	NPC472983
0.8421	Intermediate Similarity	NPC5509
0.8421	Intermediate Similarity	NPC275740
0.8421	Intermediate Similarity	NPC86319
0.8416	Intermediate Similarity	NPC477915
0.8416	Intermediate Similarity	NPC473424
0.8416	Intermediate Similarity	NPC281702
0.8404	Intermediate Similarity	NPC167877
0.84	Intermediate Similarity	NPC154072
0.84	Intermediate Similarity	NPC144660
0.84	Intermediate Similarity	NPC299971
0.84	Intermediate Similarity	NPC316964
0.84	Intermediate Similarity	NPC201406
0.84	Intermediate Similarity	NPC470074
0.84	Intermediate Similarity	NPC472644
0.84	Intermediate Similarity	NPC471041
0.84	Intermediate Similarity	NPC112167
0.84	Intermediate Similarity	NPC327431
0.8396	Intermediate Similarity	NPC264634
0.8396	Intermediate Similarity	NPC475970
0.8396	Intermediate Similarity	NPC100267
0.8396	Intermediate Similarity	NPC71348
0.8396	Intermediate Similarity	NPC475524
0.8384	Intermediate Similarity	NPC254496
0.8384	Intermediate Similarity	NPC122294
0.8384	Intermediate Similarity	NPC57416
0.8384	Intermediate Similarity	NPC43747
0.8384	Intermediate Similarity	NPC108078
0.8384	Intermediate Similarity	NPC141401
0.8384	Intermediate Similarity	NPC226986
0.8384	Intermediate Similarity	NPC69385
0.8384	Intermediate Similarity	NPC23680
0.8381	Intermediate Similarity	NPC272898
0.8381	Intermediate Similarity	NPC473036
0.8381	Intermediate Similarity	NPC197428
0.837	Intermediate Similarity	NPC97913
0.8367	Intermediate Similarity	NPC472932
0.8367	Intermediate Similarity	NPC98639
0.8367	Intermediate Similarity	NPC69548
0.8367	Intermediate Similarity	NPC183012
0.8367	Intermediate Similarity	NPC184848
0.8367	Intermediate Similarity	NPC255809
0.8367	Intermediate Similarity	NPC271195
0.8365	Intermediate Similarity	NPC189075
0.8365	Intermediate Similarity	NPC275539
0.8365	Intermediate Similarity	NPC469844
0.8351	Intermediate Similarity	NPC470375
0.8351	Intermediate Similarity	NPC107674
0.8351	Intermediate Similarity	NPC243866
0.8351	Intermediate Similarity	NPC214697
0.8351	Intermediate Similarity	NPC294263
0.8351	Intermediate Similarity	NPC109414
0.8351	Intermediate Similarity	NPC170220
0.8351	Intermediate Similarity	NPC141497
0.8351	Intermediate Similarity	NPC470224
0.8351	Intermediate Similarity	NPC470376
0.835	Intermediate Similarity	NPC97202
0.835	Intermediate Similarity	NPC49958
0.835	Intermediate Similarity	NPC48733
0.835	Intermediate Similarity	NPC296945
0.835	Intermediate Similarity	NPC260268
0.835	Intermediate Similarity	NPC50692
0.835	Intermediate Similarity	NPC202167
0.835	Intermediate Similarity	NPC96377
0.835	Intermediate Similarity	NPC319077
0.835	Intermediate Similarity	NPC476027
0.835	Intermediate Similarity	NPC152695
0.835	Intermediate Similarity	NPC171137
0.835	Intermediate Similarity	NPC150531
0.835	Intermediate Similarity	NPC181265
0.835	Intermediate Similarity	NPC214264
0.835	Intermediate Similarity	NPC85829
0.835	Intermediate Similarity	NPC302607
0.8333	Intermediate Similarity	NPC175628

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 NPC476274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1372
0.2-0.3	3673
0.3-0.4	2560
0.4-0.5	867
0.5-0.6	200
0.6-0.7	181
0.7-0.8	133
0.8-0.85	23
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8544	High Similarity	NPD6881	Approved
0.8544	High Similarity	NPD6899	Approved
0.8542	High Similarity	NPD6399	Phase 3
0.8529	High Similarity	NPD5739	Approved
0.8529	High Similarity	NPD7128	Approved
0.8529	High Similarity	NPD6675	Approved
0.8529	High Similarity	NPD6402	Approved
0.8476	Intermediate Similarity	NPD6649	Approved
0.8476	Intermediate Similarity	NPD6650	Approved
0.8462	Intermediate Similarity	NPD6372	Approved
0.8462	Intermediate Similarity	NPD6373	Approved
0.8447	Intermediate Similarity	NPD5697	Approved
0.8438	Intermediate Similarity	NPD6079	Approved
0.8421	Intermediate Similarity	NPD5328	Approved
0.8381	Intermediate Similarity	NPD7290	Approved
0.8381	Intermediate Similarity	NPD6883	Approved
0.8381	Intermediate Similarity	NPD7102	Approved
0.8365	Intermediate Similarity	NPD6011	Approved
0.8365	Intermediate Similarity	NPD7320	Approved
0.8302	Intermediate Similarity	NPD6847	Approved
0.8302	Intermediate Similarity	NPD6617	Approved
0.8302	Intermediate Similarity	NPD6869	Approved
0.8302	Intermediate Similarity	NPD8130	Phase 1
0.8286	Intermediate Similarity	NPD6012	Approved
0.8286	Intermediate Similarity	NPD6014	Approved
0.8286	Intermediate Similarity	NPD6013	Approved
0.8269	Intermediate Similarity	NPD5701	Approved
0.8235	Intermediate Similarity	NPD5211	Phase 2
0.8224	Intermediate Similarity	NPD8297	Approved
0.8224	Intermediate Similarity	NPD6882	Approved
0.8131	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD3618	Phase 1
0.81	Intermediate Similarity	NPD5222	Approved
0.81	Intermediate Similarity	NPD5221	Approved
0.81	Intermediate Similarity	NPD4697	Phase 3
0.81	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD7115	Discovery
0.8077	Intermediate Similarity	NPD5141	Approved
0.8039	Intermediate Similarity	NPD4696	Approved
0.8039	Intermediate Similarity	NPD7640	Approved
0.8039	Intermediate Similarity	NPD5286	Approved
0.8039	Intermediate Similarity	NPD7639	Approved
0.8039	Intermediate Similarity	NPD5285	Approved
0.802	Intermediate Similarity	NPD7902	Approved
0.802	Intermediate Similarity	NPD6083	Phase 2
0.802	Intermediate Similarity	NPD5173	Approved
0.802	Intermediate Similarity	NPD6084	Phase 2
0.802	Intermediate Similarity	NPD4755	Approved
0.7961	Intermediate Similarity	NPD5223	Approved
0.7941	Intermediate Similarity	NPD7638	Approved
0.7938	Intermediate Similarity	NPD5737	Approved
0.7938	Intermediate Similarity	NPD6672	Approved
0.7917	Intermediate Similarity	NPD6409	Approved
0.7917	Intermediate Similarity	NPD5330	Approved
0.7917	Intermediate Similarity	NPD7146	Approved
0.7917	Intermediate Similarity	NPD6684	Approved
0.7917	Intermediate Similarity	NPD7334	Approved
0.7917	Intermediate Similarity	NPD7521	Approved
0.79	Intermediate Similarity	NPD7748	Approved
0.7895	Intermediate Similarity	NPD4786	Approved
0.7885	Intermediate Similarity	NPD5225	Approved
0.7885	Intermediate Similarity	NPD5226	Approved
0.7885	Intermediate Similarity	NPD4633	Approved
0.7885	Intermediate Similarity	NPD5224	Approved
0.7879	Intermediate Similarity	NPD7515	Phase 2
0.7864	Intermediate Similarity	NPD4700	Approved
0.7857	Intermediate Similarity	NPD6335	Approved
0.7838	Intermediate Similarity	NPD6274	Approved
0.7838	Intermediate Similarity	NPD6868	Approved
0.783	Intermediate Similarity	NPD6008	Approved
0.7822	Intermediate Similarity	NPD5695	Phase 3
0.7818	Intermediate Similarity	NPD4632	Approved
0.781	Intermediate Similarity	NPD5175	Approved
0.781	Intermediate Similarity	NPD5174	Approved
0.78	Intermediate Similarity	NPD4202	Approved
0.7788	Intermediate Similarity	NPD7100	Approved
0.7788	Intermediate Similarity	NPD7101	Approved
0.7768	Intermediate Similarity	NPD6317	Approved
0.7767	Intermediate Similarity	NPD5696	Approved
0.7755	Intermediate Similarity	NPD6903	Approved
0.7755	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7900	Approved
0.7708	Intermediate Similarity	NPD3665	Phase 1
0.7708	Intermediate Similarity	NPD3133	Approved
0.7708	Intermediate Similarity	NPD3666	Approved
0.77	Intermediate Similarity	NPD8035	Phase 2
0.77	Intermediate Similarity	NPD5281	Approved
0.77	Intermediate Similarity	NPD8034	Phase 2
0.77	Intermediate Similarity	NPD5284	Approved
0.7699	Intermediate Similarity	NPD6314	Approved
0.7699	Intermediate Similarity	NPD6313	Approved
0.7684	Intermediate Similarity	NPD3667	Approved
0.7652	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4754	Approved
0.7634	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD1694	Approved
0.7611	Intermediate Similarity	NPD6009	Approved
0.76	Intermediate Similarity	NPD5785	Approved
0.7596	Intermediate Similarity	NPD4225	Approved
0.7565	Intermediate Similarity	NPD6319	Approved
0.7551	Intermediate Similarity	NPD5279	Phase 3
0.7523	Intermediate Similarity	NPD5128	Approved
0.7523	Intermediate Similarity	NPD4730	Approved
0.7523	Intermediate Similarity	NPD4729	Approved
0.7521	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD6909	Approved
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD5983	Phase 2
0.75	Intermediate Similarity	NPD6908	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD4767	Approved
0.7476	Intermediate Similarity	NPD4629	Approved
0.7476	Intermediate Similarity	NPD5210	Approved
0.7475	Intermediate Similarity	NPD3573	Approved
0.7458	Intermediate Similarity	NPD7492	Approved
0.7451	Intermediate Similarity	NPD5778	Approved
0.7451	Intermediate Similarity	NPD5779	Approved
0.7449	Intermediate Similarity	NPD5363	Approved
0.7449	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6054	Approved
0.7411	Intermediate Similarity	NPD6053	Discontinued
0.7395	Intermediate Similarity	NPD6616	Approved
0.7395	Intermediate Similarity	NPD6336	Discontinued
0.7387	Intermediate Similarity	NPD5249	Phase 3
0.7387	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5248	Approved
0.7387	Intermediate Similarity	NPD4634	Approved
0.7387	Intermediate Similarity	NPD5250	Approved
0.7387	Intermediate Similarity	NPD5135	Approved
0.7387	Intermediate Similarity	NPD5251	Approved
0.7387	Intermediate Similarity	NPD5247	Approved
0.7387	Intermediate Similarity	NPD5169	Approved
0.7383	Intermediate Similarity	NPD7632	Discontinued
0.7374	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5786	Approved
0.7364	Intermediate Similarity	NPD5168	Approved
0.7353	Intermediate Similarity	NPD6411	Approved
0.7353	Intermediate Similarity	NPD5693	Phase 1
0.7353	Intermediate Similarity	NPD6050	Approved
0.7333	Intermediate Similarity	NPD7078	Approved
0.7321	Intermediate Similarity	NPD5215	Approved
0.7321	Intermediate Similarity	NPD5127	Approved
0.7321	Intermediate Similarity	NPD5216	Approved
0.7321	Intermediate Similarity	NPD5217	Approved
0.732	Intermediate Similarity	NPD6435	Approved
0.732	Intermediate Similarity	NPD4221	Approved
0.732	Intermediate Similarity	NPD4223	Phase 3
0.7308	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6370	Approved
0.7273	Intermediate Similarity	NPD5329	Approved
0.7273	Intermediate Similarity	NPD7736	Approved
0.7273	Intermediate Similarity	NPD6412	Phase 2
0.7265	Intermediate Similarity	NPD6059	Approved
0.7255	Intermediate Similarity	NPD5207	Approved
0.7255	Intermediate Similarity	NPD5692	Phase 3
0.725	Intermediate Similarity	NPD7507	Approved
0.7245	Intermediate Similarity	NPD5362	Discontinued
0.7228	Intermediate Similarity	NPD5208	Approved
0.7212	Intermediate Similarity	NPD6001	Approved
0.7207	Intermediate Similarity	NPD6686	Approved
0.7203	Intermediate Similarity	NPD6015	Approved
0.7203	Intermediate Similarity	NPD6016	Approved
0.72	Intermediate Similarity	NPD6098	Approved
0.72	Intermediate Similarity	NPD5690	Phase 2
0.7196	Intermediate Similarity	NPD6404	Discontinued
0.719	Intermediate Similarity	NPD8293	Discontinued
0.7184	Intermediate Similarity	NPD7637	Suspended
0.7184	Intermediate Similarity	NPD5694	Approved
0.7172	Intermediate Similarity	NPD4197	Approved
0.7172	Intermediate Similarity	NPD3668	Phase 3
0.7157	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD4270	Approved
0.7143	Intermediate Similarity	NPD5988	Approved
0.7143	Intermediate Similarity	NPD4269	Approved
0.713	Intermediate Similarity	NPD5167	Approved
0.7113	Intermediate Similarity	NPD5368	Approved
0.7113	Intermediate Similarity	NPD7525	Registered
0.7073	Intermediate Similarity	NPD7319	Approved
0.7071	Intermediate Similarity	NPD4788	Approved
0.703	Intermediate Similarity	NPD5205	Approved
0.703	Intermediate Similarity	NPD4519	Discontinued
0.703	Intermediate Similarity	NPD4688	Approved
0.703	Intermediate Similarity	NPD4623	Approved
0.703	Intermediate Similarity	NPD4689	Approved
0.703	Intermediate Similarity	NPD5280	Approved
0.703	Intermediate Similarity	NPD4693	Phase 3
0.703	Intermediate Similarity	NPD4690	Approved
0.703	Intermediate Similarity	NPD4694	Approved
0.703	Intermediate Similarity	NPD4138	Approved
0.6991	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6051	Approved
0.6979	Remote Similarity	NPD6116	Phase 1
0.6947	Remote Similarity	NPD6942	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