NPASS Compound

Structure

CID309603 OpenBabel06191716122D 31 34 0 0 1 0 0 0 0 0999 V2000 -5.8198 5.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8189 2.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2815 2.9242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8945 3.7697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3071 4.6131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3567 2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8444 3.7692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2254 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2251 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6910 1.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 -0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3066 2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3817 2.9253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8194 3.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6895 -0.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3815 1.9503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5358 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 0.4877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -1.4642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5361 1.4626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5558 -1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 -2.4642 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 3 18 1 0 0 0 0 7 20 2 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 23 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 21 1 0 0 0 0 16 26 2 0 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 19 4 1 1 0 0 0 19 23 1 0 0 0 0 21 30 2 0 0 0 0 22 17 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 6 0 0 0 24 28 1 6 0 0 0 25 29 1 6 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 27 31 1 6 0 0 0 28 5 1 6 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.35
Volume:	485.585
LogP:	6.202
LogD:	6.581
LogS:	-5.619
# Rotatable Bonds:	5
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	4.611
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.855
MDCK Permeability:	1.0230373845843133e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.898
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.8
Plasma Protein Binding (PPB):	92.06847381591797%
Volume Distribution (VD):	1.341
Pgp-substrate:	1.752496361732483%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.552
CYP2C19-inhibitor:	0.182
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.378
CYP2C9-substrate:	0.303
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.623
CYP3A4-inhibitor:	0.614
CYP3A4-substrate:	0.554

ADMET: Excretion

Clearance (CL):	6.567
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.132
Human Hepatotoxicity (H-HT):	0.535
Drug-inuced Liver Injury (DILI):	0.755
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.199
Maximum Recommended Daily Dose:	0.143
Skin Sensitization:	0.703
Carcinogencity:	0.055
Eye Corrosion:	0.065
Eye Irritation:	0.103
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC309603

Natural Product ID:	NPC309603
*Common Name:**	6Beta-Hydroxy-24-Ethylcholesta-4,24(28)-Dien-3-One
IUPAC Name:	(6R,8S,9S,10R,13R,14S,17R)-6-hydroxy-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	PRKRLDJHSWQHED-CLUHYBOGSA-N
Standard InCHI:	InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h7,16,18-19,22-25,27,31H,8-15,17H2,1-6H3/b20-7+/t19-,22+,23-,24+,25+,27-,28-,29-/m1/s1
SMILES:	C/C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@H](C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)O)/C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485978
PubChem CID:	10717343
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO16318	Turbinaria conoides	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075746]
NPO6567	Aesculus x carnea	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15720	Russula flavida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20447	Ichthyothere rufa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18754	Agathosma capensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27825	Diospyros sapota	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16768	Tortella inclinata	Species	Pottiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6567	Aesculus x carnea	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21457	Schefflera taiwaniana	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16318	Turbinaria conoides	Species	Sargassaceae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.9	ug ml-1	PMID[537365]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.6	ug ml-1	PMID[537365]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.3	ug ml-1	PMID[537365]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.2	ug ml-1	PMID[537365]

☑ 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 NPC309603 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	159
0.1-0.2	1047
0.2-0.3	4413
0.3-0.4	12657
0.4-0.5	10002
0.5-0.6	6234
0.6-0.7	4956
0.7-0.8	2612
0.8-0.85	413
0.85-0.9	155
0.9-0.95	39
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473999
0.9765	High Similarity	NPC473998
0.9765	High Similarity	NPC475806
0.9647	High Similarity	NPC48010
0.954	High Similarity	NPC8993
0.9518	High Similarity	NPC471224
0.9432	High Similarity	NPC271195
0.9425	High Similarity	NPC69454
0.9405	High Similarity	NPC145879
0.9405	High Similarity	NPC474778
0.9405	High Similarity	NPC31564
0.9405	High Similarity	NPC474732
0.9405	High Similarity	NPC474733
0.9398	High Similarity	NPC214043
0.9398	High Similarity	NPC85774
0.931	High Similarity	NPC63748
0.931	High Similarity	NPC233116
0.9294	High Similarity	NPC58063
0.9294	High Similarity	NPC475740
0.9286	High Similarity	NPC474083
0.9286	High Similarity	NPC470574
0.9213	High Similarity	NPC259286
0.9205	High Similarity	NPC474736
0.9205	High Similarity	NPC109305
0.9186	High Similarity	NPC471722
0.9186	High Similarity	NPC328539
0.9176	High Similarity	NPC72133
0.9176	High Similarity	NPC469994
0.9167	High Similarity	NPC59453
0.9167	High Similarity	NPC473246
0.9167	High Similarity	NPC221758
0.9121	High Similarity	NPC103051
0.9111	High Similarity	NPC249954
0.9091	High Similarity	NPC272746
0.908	High Similarity	NPC31985
0.908	High Similarity	NPC2983
0.908	High Similarity	NPC86319
0.908	High Similarity	NPC186688
0.908	High Similarity	NPC268406
0.908	High Similarity	NPC26959
0.908	High Similarity	NPC275740
0.908	High Similarity	NPC1015
0.9059	High Similarity	NPC469948
0.9022	High Similarity	NPC154072
0.8989	High Similarity	NPC472930
0.8989	High Similarity	NPC475255
0.8977	High Similarity	NPC126993
0.8977	High Similarity	NPC191684
0.8977	High Similarity	NPC85173
0.8966	High Similarity	NPC143767
0.8966	High Similarity	NPC131470
0.8953	High Similarity	NPC222613
0.8953	High Similarity	NPC472985
0.8953	High Similarity	NPC475022
0.8953	High Similarity	NPC118648
0.8953	High Similarity	NPC472986
0.8953	High Similarity	NPC51014
0.8941	High Similarity	NPC321187
0.8941	High Similarity	NPC82902
0.8941	High Similarity	NPC329043
0.8941	High Similarity	NPC472265
0.8941	High Similarity	NPC58841
0.8941	High Similarity	NPC161423
0.8941	High Similarity	NPC227064
0.8941	High Similarity	NPC237712
0.8929	High Similarity	NPC151519
0.8889	High Similarity	NPC474690
0.8889	High Similarity	NPC245972
0.8889	High Similarity	NPC299100
0.8889	High Similarity	NPC196485
0.8889	High Similarity	NPC111015
0.8876	High Similarity	NPC185936
0.8876	High Similarity	NPC168027
0.8864	High Similarity	NPC262858
0.8864	High Similarity	NPC472971
0.8864	High Similarity	NPC472970
0.8864	High Similarity	NPC472973
0.8864	High Similarity	NPC477943
0.8864	High Similarity	NPC119416
0.8864	High Similarity	NPC472240
0.8851	High Similarity	NPC93778
0.8851	High Similarity	NPC142361
0.8851	High Similarity	NPC141292
0.8851	High Similarity	NPC317590
0.8851	High Similarity	NPC474684
0.8837	High Similarity	NPC474218
0.883	High Similarity	NPC477915
0.8804	High Similarity	NPC253826
0.8804	High Similarity	NPC320306
0.8795	High Similarity	NPC209430
0.8795	High Similarity	NPC308038
0.8795	High Similarity	NPC30986
0.8791	High Similarity	NPC476174
0.8791	High Similarity	NPC180950
0.8791	High Similarity	NPC472932
0.8778	High Similarity	NPC12722
0.8764	High Similarity	NPC183283
0.8764	High Similarity	NPC320026
0.8764	High Similarity	NPC69622
0.875	High Similarity	NPC193360
0.875	High Similarity	NPC292491
0.875	High Similarity	NPC310752
0.875	High Similarity	NPC471724
0.875	High Similarity	NPC328313
0.8737	High Similarity	NPC249187
0.8737	High Similarity	NPC247957
0.8736	High Similarity	NPC327115
0.8736	High Similarity	NPC94755
0.8736	High Similarity	NPC155011
0.8721	High Similarity	NPC165064
0.8721	High Similarity	NPC33913
0.8721	High Similarity	NPC476412
0.8706	High Similarity	NPC93590
0.8696	High Similarity	NPC250757
0.8696	High Similarity	NPC472941
0.8696	High Similarity	NPC456
0.8696	High Similarity	NPC471463
0.8696	High Similarity	NPC301534
0.8696	High Similarity	NPC117133
0.869	High Similarity	NPC2482
0.869	High Similarity	NPC472478
0.8681	High Similarity	NPC292793
0.8681	High Similarity	NPC469406
0.8667	High Similarity	NPC472978
0.8652	High Similarity	NPC214387
0.8652	High Similarity	NPC146554
0.8652	High Similarity	NPC32830
0.8652	High Similarity	NPC472983
0.8652	High Similarity	NPC474704
0.8652	High Similarity	NPC123912
0.8652	High Similarity	NPC76879
0.8652	High Similarity	NPC474245
0.8652	High Similarity	NPC475921
0.8646	High Similarity	NPC204833
0.8646	High Similarity	NPC209502
0.8646	High Similarity	NPC72255
0.8636	High Similarity	NPC187376
0.8636	High Similarity	NPC90652
0.8636	High Similarity	NPC136948
0.8636	High Similarity	NPC159046
0.8636	High Similarity	NPC233836
0.8636	High Similarity	NPC136548
0.8636	High Similarity	NPC287079
0.8632	High Similarity	NPC293753
0.8632	High Similarity	NPC473424
0.8632	High Similarity	NPC234892
0.8621	High Similarity	NPC274724
0.8621	High Similarity	NPC476426
0.8621	High Similarity	NPC197823
0.8621	High Similarity	NPC292553
0.8617	High Similarity	NPC327431
0.8617	High Similarity	NPC476274
0.8605	High Similarity	NPC476082
0.8605	High Similarity	NPC470046
0.8605	High Similarity	NPC470047
0.8605	High Similarity	NPC278648
0.8605	High Similarity	NPC41539
0.8602	High Similarity	NPC474938
0.8602	High Similarity	NPC474785
0.8602	High Similarity	NPC108078
0.8587	High Similarity	NPC297199
0.8587	High Similarity	NPC318282
0.8587	High Similarity	NPC174948
0.8587	High Similarity	NPC469995
0.8587	High Similarity	NPC173875
0.8571	High Similarity	NPC477520
0.8571	High Similarity	NPC143182
0.8571	High Similarity	NPC28862
0.8571	High Similarity	NPC47982
0.8571	High Similarity	NPC84694
0.8571	High Similarity	NPC81306
0.8571	High Similarity	NPC109546
0.8571	High Similarity	NPC472942
0.8557	High Similarity	NPC97202
0.8557	High Similarity	NPC49958
0.8557	High Similarity	NPC150531
0.8557	High Similarity	NPC302607
0.8557	High Similarity	NPC202167
0.8557	High Similarity	NPC214264
0.8557	High Similarity	NPC152695
0.8557	High Similarity	NPC149047
0.8557	High Similarity	NPC171137
0.8557	High Similarity	NPC296945
0.8557	High Similarity	NPC260268
0.8557	High Similarity	NPC257353
0.8557	High Similarity	NPC476027
0.8557	High Similarity	NPC48733
0.8557	High Similarity	NPC50692
0.8557	High Similarity	NPC85829
0.8557	High Similarity	NPC319077
0.8556	High Similarity	NPC477149
0.8556	High Similarity	NPC477147
0.8556	High Similarity	NPC469400
0.8542	High Similarity	NPC311612
0.8539	High Similarity	NPC474677
0.8539	High Similarity	NPC470417
0.8539	High Similarity	NPC53911
0.8539	High Similarity	NPC472802
0.8526	High Similarity	NPC476223
0.8526	High Similarity	NPC476240

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 NPC309603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1353
0.2-0.3	3900
0.3-0.4	2585
0.4-0.5	663
0.5-0.6	166
0.6-0.7	121
0.7-0.8	156
0.8-0.85	45
0.85-0.9	11
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9302	High Similarity	NPD5328	Approved
0.9176	High Similarity	NPD3618	Phase 1
0.9167	High Similarity	NPD4786	Approved
0.9091	High Similarity	NPD6079	Approved
0.8941	High Similarity	NPD3665	Phase 1
0.8941	High Similarity	NPD3133	Approved
0.8941	High Similarity	NPD3666	Approved
0.8929	High Similarity	NPD3667	Approved
0.8778	High Similarity	NPD4202	Approved
0.8523	High Similarity	NPD5279	Phase 3
0.8495	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8495	Intermediate Similarity	NPD4697	Phase 3
0.8495	Intermediate Similarity	NPD5221	Approved
0.8495	Intermediate Similarity	NPD5222	Approved
0.8488	Intermediate Similarity	NPD4223	Phase 3
0.8488	Intermediate Similarity	NPD4221	Approved
0.8444	Intermediate Similarity	NPD4753	Phase 2
0.8438	Intermediate Similarity	NPD5211	Phase 2
0.8409	Intermediate Similarity	NPD5329	Approved
0.8404	Intermediate Similarity	NPD4755	Approved
0.8404	Intermediate Similarity	NPD5173	Approved
0.8295	Intermediate Similarity	NPD4197	Approved
0.8265	Intermediate Similarity	NPD5141	Approved
0.8261	Intermediate Similarity	NPD7515	Phase 2
0.8229	Intermediate Similarity	NPD5286	Approved
0.8229	Intermediate Similarity	NPD4700	Approved
0.8229	Intermediate Similarity	NPD4696	Approved
0.8229	Intermediate Similarity	NPD5285	Approved
0.8172	Intermediate Similarity	NPD6399	Phase 3
0.8144	Intermediate Similarity	NPD5223	Approved
0.8111	Intermediate Similarity	NPD7521	Approved
0.8111	Intermediate Similarity	NPD4519	Discontinued
0.8111	Intermediate Similarity	NPD7334	Approved
0.8111	Intermediate Similarity	NPD4693	Phase 3
0.8111	Intermediate Similarity	NPD4690	Approved
0.8111	Intermediate Similarity	NPD6684	Approved
0.8111	Intermediate Similarity	NPD4688	Approved
0.8111	Intermediate Similarity	NPD5205	Approved
0.8111	Intermediate Similarity	NPD4689	Approved
0.8111	Intermediate Similarity	NPD6409	Approved
0.8111	Intermediate Similarity	NPD7146	Approved
0.8111	Intermediate Similarity	NPD5330	Approved
0.8111	Intermediate Similarity	NPD4623	Approved
0.8111	Intermediate Similarity	NPD4138	Approved
0.8095	Intermediate Similarity	NPD7339	Approved
0.8095	Intermediate Similarity	NPD6942	Approved
0.809	Intermediate Similarity	NPD3668	Phase 3
0.8061	Intermediate Similarity	NPD5224	Approved
0.8061	Intermediate Similarity	NPD4633	Approved
0.8061	Intermediate Similarity	NPD5225	Approved
0.8061	Intermediate Similarity	NPD5226	Approved
0.8041	Intermediate Similarity	NPD7640	Approved
0.8041	Intermediate Similarity	NPD7639	Approved
0.8023	Intermediate Similarity	NPD3617	Approved
0.8021	Intermediate Similarity	NPD6083	Phase 2
0.8021	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD4629	Approved
0.8	Intermediate Similarity	NPD5210	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.798	Intermediate Similarity	NPD5174	Approved
0.798	Intermediate Similarity	NPD5175	Approved
0.798	Intermediate Similarity	NPD4754	Approved
0.7978	Intermediate Similarity	NPD4788	Approved
0.7938	Intermediate Similarity	NPD7638	Approved
0.7935	Intermediate Similarity	NPD6903	Approved
0.7935	Intermediate Similarity	NPD5737	Approved
0.7935	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6672	Approved
0.7912	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD4694	Approved
0.7912	Intermediate Similarity	NPD5280	Approved
0.7912	Intermediate Similarity	NPD5690	Phase 2
0.7895	Intermediate Similarity	NPD7748	Approved
0.7843	Intermediate Similarity	NPD6899	Approved
0.7843	Intermediate Similarity	NPD7320	Approved
0.7843	Intermediate Similarity	NPD6881	Approved
0.7841	Intermediate Similarity	NPD7525	Registered
0.7831	Intermediate Similarity	NPD4747	Approved
0.7822	Intermediate Similarity	NPD4767	Approved
0.7822	Intermediate Similarity	NPD4768	Approved
0.7791	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD6372	Approved
0.7767	Intermediate Similarity	NPD6373	Approved
0.7757	Intermediate Similarity	NPD7115	Discovery
0.7745	Intermediate Similarity	NPD5701	Approved
0.7745	Intermediate Similarity	NPD5697	Approved
0.7738	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4195	Approved
0.7711	Intermediate Similarity	NPD4137	Phase 3
0.7692	Intermediate Similarity	NPD7102	Approved
0.7692	Intermediate Similarity	NPD7290	Approved
0.7692	Intermediate Similarity	NPD6883	Approved
0.767	Intermediate Similarity	NPD6011	Approved
0.767	Intermediate Similarity	NPD4729	Approved
0.767	Intermediate Similarity	NPD5168	Approved
0.767	Intermediate Similarity	NPD5128	Approved
0.767	Intermediate Similarity	NPD4730	Approved
0.7653	Intermediate Similarity	NPD7902	Approved
0.764	Intermediate Similarity	NPD4695	Discontinued
0.7634	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD5695	Phase 3
0.7619	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4691	Approved
0.7619	Intermediate Similarity	NPD6869	Approved
0.7619	Intermediate Similarity	NPD6649	Approved
0.7619	Intermediate Similarity	NPD6847	Approved
0.7619	Intermediate Similarity	NPD6650	Approved
0.7619	Intermediate Similarity	NPD8130	Phase 1
0.7619	Intermediate Similarity	NPD6617	Approved
0.7614	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6013	Approved
0.7596	Intermediate Similarity	NPD6012	Approved
0.7596	Intermediate Similarity	NPD6014	Approved
0.7576	Intermediate Similarity	NPD5696	Approved
0.7558	Intermediate Similarity	NPD5733	Approved
0.7547	Intermediate Similarity	NPD8297	Approved
0.7547	Intermediate Similarity	NPD6882	Approved
0.7524	Intermediate Similarity	NPD4634	Approved
0.7524	Intermediate Similarity	NPD5249	Phase 3
0.7524	Intermediate Similarity	NPD5251	Approved
0.7524	Intermediate Similarity	NPD5247	Approved
0.7524	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5135	Approved
0.7524	Intermediate Similarity	NPD5248	Approved
0.7524	Intermediate Similarity	NPD5169	Approved
0.7524	Intermediate Similarity	NPD5250	Approved
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5284	Approved
0.7474	Intermediate Similarity	NPD6080	Approved
0.7474	Intermediate Similarity	NPD6673	Approved
0.7474	Intermediate Similarity	NPD6904	Approved
0.7453	Intermediate Similarity	NPD5215	Approved
0.7453	Intermediate Similarity	NPD5127	Approved
0.7453	Intermediate Similarity	NPD5217	Approved
0.7453	Intermediate Similarity	NPD5216	Approved
0.7449	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD6412	Phase 2
0.7396	Intermediate Similarity	NPD4096	Approved
0.7368	Intermediate Similarity	NPD5208	Approved
0.7363	Intermediate Similarity	NPD4139	Approved
0.7363	Intermediate Similarity	NPD4692	Approved
0.7356	Intermediate Similarity	NPD4687	Approved
0.7356	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6926	Approved
0.7356	Intermediate Similarity	NPD4058	Approved
0.7356	Intermediate Similarity	NPD6924	Approved
0.7353	Intermediate Similarity	NPD7632	Discontinued
0.7347	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6098	Approved
0.7339	Intermediate Similarity	NPD6868	Approved
0.7333	Intermediate Similarity	NPD6929	Approved
0.7333	Intermediate Similarity	NPD7645	Phase 2
0.7327	Intermediate Similarity	NPD6404	Discontinued
0.7326	Intermediate Similarity	NPD5276	Approved
0.7326	Intermediate Similarity	NPD4243	Approved
0.732	Intermediate Similarity	NPD8035	Phase 2
0.732	Intermediate Similarity	NPD5693	Phase 1
0.732	Intermediate Similarity	NPD8034	Phase 2
0.7315	Intermediate Similarity	NPD4632	Approved
0.7253	Intermediate Similarity	NPD6930	Phase 2
0.7253	Intermediate Similarity	NPD6931	Approved
0.7248	Intermediate Similarity	NPD5167	Approved
0.7245	Intermediate Similarity	NPD5133	Approved
0.7234	Intermediate Similarity	NPD1696	Phase 3
0.7229	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5290	Discontinued
0.7209	Intermediate Similarity	NPD4245	Approved
0.7209	Intermediate Similarity	NPD4789	Approved
0.7209	Intermediate Similarity	NPD4244	Approved
0.7207	Intermediate Similarity	NPD6335	Approved
0.7191	Intermediate Similarity	NPD6933	Approved
0.7191	Intermediate Similarity	NPD6117	Approved
0.7188	Intermediate Similarity	NPD4518	Approved
0.7182	Intermediate Similarity	NPD6274	Approved
0.7176	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5360	Phase 3
0.7172	Intermediate Similarity	NPD6001	Approved
0.7159	Intermediate Similarity	NPD4784	Approved
0.7159	Intermediate Similarity	NPD4785	Approved
0.7143	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD7100	Approved
0.7143	Intermediate Similarity	NPD6050	Approved
0.7143	Intermediate Similarity	NPD7101	Approved
0.7126	Intermediate Similarity	NPD7150	Approved
0.7126	Intermediate Similarity	NPD7151	Approved
0.7126	Intermediate Similarity	NPD7152	Approved
0.7117	Intermediate Similarity	NPD6317	Approved
0.7117	Intermediate Similarity	NPD6009	Approved
0.7113	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5776	Phase 2
0.7111	Intermediate Similarity	NPD6116	Phase 1

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