NPASS Compound

Structure

NPC475867 OpenBabel07101718242D 34 37 0 0 1 0 0 0 0 0999 V2000 7.6623 4.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3022 6.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6549 6.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3751 3.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7302 2.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6842 4.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7279 4.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0369 4.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6758 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3240 6.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3970 3.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0150 5.1622 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0880 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 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 4.1369 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 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 0.2788 -1.7601 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 7 34 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 12 25 2 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 21 11 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 24 29 1 1 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 26 31 2 0 0 0 0 27 30 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 5 1 1 0 0 0 29 6 1 1 0 0 0 30 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	7.302
LogD:	6.675
LogS:	-5.643
# Rotatable Bonds:	8
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.272
Synthetic Accessibility Score:	5.003
Fsp3:	0.867
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:	-4.77
MDCK Permeability:	4.04071033699438e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.254
30% Bioavailability (F30%):	0.806

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.688
Plasma Protein Binding (PPB):	96.81301879882812%
Volume Distribution (VD):	1.194
Pgp-substrate:	1.813615322113037%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.671
CYP2C19-inhibitor:	0.385
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.569
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.857

ADMET: Excretion

Clearance (CL):	8.855
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.504
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.617
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.18
Carcinogencity:	0.06
Eye Corrosion:	0.638
Eye Irritation:	0.056
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC475867

Natural Product ID:	NPC475867
*Common Name:**	Phorbasterone D
IUPAC Name:	methyl (2S,3aR,3bS,5aR,6R,8aS,8bS)-6-[(2R)-5-ethyl-6-methylheptan-2-yl]-2-hydroxy-3a,5a-dimethyl-1-oxo-3,3b,4,5,6,7,8,8a,8b,9-decahydroindeno[5,4-e]indene-2-carboxylate
Synonyms:	Phorbasterone D
Standard InCHIKey:	FXOGEPKTXCIWPW-RZZHZTBNSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-8-20(18(2)3)10-9-19(4)22-13-14-23-21-11-12-25-26(31)30(33,27(32)34-7)17-29(25,6)24(21)15-16-28(22,23)5/h12,18-24,33H,8-11,13-17H2,1-7H3/t19-,20?,21+,22-,23+,24+,28-,29-,30+/m1/s1
SMILES:	CCC(C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)C[C@@](C2=O)(O)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517644
PubChem CID:	23248536
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003568] Androstane 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
NPO25324	Phorbas amaranthus	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104518]
NPO25324	Phorbas amaranthus	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[464183]

☑ 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 NPC475867 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	210
0.1-0.2	1323
0.2-0.3	6093
0.3-0.4	12679
0.4-0.5	9246
0.5-0.6	7464
0.6-0.7	4806
0.7-0.8	869
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC270155
0.9789	High Similarity	NPC474330
0.9789	High Similarity	NPC474207
0.9688	High Similarity	NPC13385
0.8286	Intermediate Similarity	NPC469508
0.8085	Intermediate Similarity	NPC477373
0.8037	Intermediate Similarity	NPC470257
0.802	Intermediate Similarity	NPC472734
0.802	Intermediate Similarity	NPC472733
0.8	Intermediate Similarity	NPC235889
0.8	Intermediate Similarity	NPC255309
0.7959	Intermediate Similarity	NPC476733
0.7959	Intermediate Similarity	NPC215029
0.7941	Intermediate Similarity	NPC472732
0.7941	Intermediate Similarity	NPC472731
0.7925	Intermediate Similarity	NPC96377
0.7925	Intermediate Similarity	NPC181265
0.7917	Intermediate Similarity	NPC474680
0.7872	Intermediate Similarity	NPC477372
0.7864	Intermediate Similarity	NPC177680
0.7864	Intermediate Similarity	NPC197386
0.7864	Intermediate Similarity	NPC153776
0.7864	Intermediate Similarity	NPC472729
0.7864	Intermediate Similarity	NPC472730
0.7864	Intermediate Similarity	NPC147954
0.785	Intermediate Similarity	NPC58370
0.785	Intermediate Similarity	NPC475294
0.785	Intermediate Similarity	NPC472925
0.785	Intermediate Similarity	NPC43285
0.7845	Intermediate Similarity	NPC473255
0.7843	Intermediate Similarity	NPC328162
0.7843	Intermediate Similarity	NPC305483
0.7843	Intermediate Similarity	NPC96859
0.7818	Intermediate Similarity	NPC191620
0.781	Intermediate Similarity	NPC119601
0.781	Intermediate Similarity	NPC473928
0.781	Intermediate Similarity	NPC308726
0.7798	Intermediate Similarity	NPC5284
0.7798	Intermediate Similarity	NPC473627
0.7798	Intermediate Similarity	NPC37116
0.7788	Intermediate Similarity	NPC472727
0.7788	Intermediate Similarity	NPC316964
0.7788	Intermediate Similarity	NPC472728
0.7778	Intermediate Similarity	NPC474570
0.7778	Intermediate Similarity	NPC305039
0.7778	Intermediate Similarity	NPC262043
0.7767	Intermediate Similarity	NPC43747
0.7767	Intermediate Similarity	NPC27105
0.7755	Intermediate Similarity	NPC136948
0.7755	Intermediate Similarity	NPC96496
0.7748	Intermediate Similarity	NPC194100
0.7745	Intermediate Similarity	NPC777
0.7745	Intermediate Similarity	NPC470016
0.7745	Intermediate Similarity	NPC317586
0.7739	Intermediate Similarity	NPC470921
0.7736	Intermediate Similarity	NPC264048
0.7732	Intermediate Similarity	NPC29447
0.7727	Intermediate Similarity	NPC43775
0.7727	Intermediate Similarity	NPC470961
0.7723	Intermediate Similarity	NPC109414
0.7723	Intermediate Similarity	NPC474807
0.7723	Intermediate Similarity	NPC25750
0.7714	Intermediate Similarity	NPC475099
0.7714	Intermediate Similarity	NPC472924
0.7714	Intermediate Similarity	NPC302537
0.7714	Intermediate Similarity	NPC163372
0.7712	Intermediate Similarity	NPC470882
0.7712	Intermediate Similarity	NPC473253
0.7712	Intermediate Similarity	NPC473265
0.7708	Intermediate Similarity	NPC168188
0.7708	Intermediate Similarity	NPC470015
0.7708	Intermediate Similarity	NPC105803
0.7706	Intermediate Similarity	NPC41405
0.7706	Intermediate Similarity	NPC475941
0.7706	Intermediate Similarity	NPC241927
0.7706	Intermediate Similarity	NPC258543
0.7706	Intermediate Similarity	NPC304495
0.7706	Intermediate Similarity	NPC474901
0.77	Intermediate Similarity	NPC289213
0.7699	Intermediate Similarity	NPC239273
0.7699	Intermediate Similarity	NPC471854
0.7692	Intermediate Similarity	NPC472687
0.7692	Intermediate Similarity	NPC471330
0.7692	Intermediate Similarity	NPC471331
0.7692	Intermediate Similarity	NPC203388
0.7692	Intermediate Similarity	NPC99657
0.7685	Intermediate Similarity	NPC220974
0.7685	Intermediate Similarity	NPC44063
0.7677	Intermediate Similarity	NPC472870
0.767	Intermediate Similarity	NPC471463
0.767	Intermediate Similarity	NPC328371
0.767	Intermediate Similarity	NPC125622
0.767	Intermediate Similarity	NPC269492
0.766	Intermediate Similarity	NPC477371
0.7658	Intermediate Similarity	NPC100267
0.7658	Intermediate Similarity	NPC475524
0.7658	Intermediate Similarity	NPC221144
0.7653	Intermediate Similarity	NPC229717
0.7647	Intermediate Similarity	NPC166906
0.7647	Intermediate Similarity	NPC124207
0.7642	Intermediate Similarity	NPC271266
0.7642	Intermediate Similarity	NPC87351
0.7642	Intermediate Similarity	NPC473163
0.7642	Intermediate Similarity	NPC473424
0.7642	Intermediate Similarity	NPC308351
0.7636	Intermediate Similarity	NPC29133
0.7636	Intermediate Similarity	NPC239097
0.7632	Intermediate Similarity	NPC311554
0.7632	Intermediate Similarity	NPC329736
0.7632	Intermediate Similarity	NPC257457
0.7629	Intermediate Similarity	NPC164577
0.7629	Intermediate Similarity	NPC144258
0.7624	Intermediate Similarity	NPC204341
0.7619	Intermediate Similarity	NPC476274
0.7619	Intermediate Similarity	NPC474720
0.7619	Intermediate Similarity	NPC88198
0.7611	Intermediate Similarity	NPC190286
0.7611	Intermediate Similarity	NPC270929
0.7607	Intermediate Similarity	NPC120724
0.7604	Intermediate Similarity	NPC327969
0.7604	Intermediate Similarity	NPC321289
0.7604	Intermediate Similarity	NPC133391
0.7604	Intermediate Similarity	NPC260956
0.7604	Intermediate Similarity	NPC100297
0.7604	Intermediate Similarity	NPC320514
0.76	Intermediate Similarity	NPC310010
0.76	Intermediate Similarity	NPC326627
0.7596	Intermediate Similarity	NPC18319
0.7596	Intermediate Similarity	NPC472690
0.7596	Intermediate Similarity	NPC477268
0.7596	Intermediate Similarity	NPC472689
0.7596	Intermediate Similarity	NPC477267
0.7593	Intermediate Similarity	NPC471332
0.7593	Intermediate Similarity	NPC292588
0.7593	Intermediate Similarity	NPC471333
0.7589	Intermediate Similarity	NPC472926
0.7589	Intermediate Similarity	NPC472929
0.7586	Intermediate Similarity	NPC46570
0.7583	Intermediate Similarity	NPC470880
0.7576	Intermediate Similarity	NPC167877
0.7576	Intermediate Similarity	NPC128644
0.7573	Intermediate Similarity	NPC173875
0.7573	Intermediate Similarity	NPC241156
0.7573	Intermediate Similarity	NPC318282
0.7573	Intermediate Similarity	NPC469995
0.7573	Intermediate Similarity	NPC171395
0.7573	Intermediate Similarity	NPC469599
0.7573	Intermediate Similarity	NPC174948
0.757	Intermediate Similarity	NPC311612
0.757	Intermediate Similarity	NPC117185
0.757	Intermediate Similarity	NPC111323
0.757	Intermediate Similarity	NPC236390
0.7568	Intermediate Similarity	NPC214797
0.7568	Intermediate Similarity	NPC472928
0.7568	Intermediate Similarity	NPC231589
0.7568	Intermediate Similarity	NPC118860
0.7565	Intermediate Similarity	NPC61520
0.7565	Intermediate Similarity	NPC473203
0.7553	Intermediate Similarity	NPC321514
0.7551	Intermediate Similarity	NPC469948
0.7551	Intermediate Similarity	NPC94531
0.7551	Intermediate Similarity	NPC473038
0.7551	Intermediate Similarity	NPC123319
0.7551	Intermediate Similarity	NPC142649
0.7551	Intermediate Similarity	NPC311702
0.7549	Intermediate Similarity	NPC206810
0.7549	Intermediate Similarity	NPC477436
0.7549	Intermediate Similarity	NPC477435
0.7547	Intermediate Similarity	NPC124211
0.7547	Intermediate Similarity	NPC473514
0.7547	Intermediate Similarity	NPC476240
0.7547	Intermediate Similarity	NPC99411
0.7547	Intermediate Similarity	NPC476223
0.7547	Intermediate Similarity	NPC224720
0.7545	Intermediate Similarity	NPC2766
0.7545	Intermediate Similarity	NPC170221
0.7545	Intermediate Similarity	NPC10064
0.7545	Intermediate Similarity	NPC214644
0.7544	Intermediate Similarity	NPC476965
0.7544	Intermediate Similarity	NPC472934
0.7544	Intermediate Similarity	NPC470959
0.7526	Intermediate Similarity	NPC97913
0.7524	Intermediate Similarity	NPC235464
0.7524	Intermediate Similarity	NPC166745
0.7524	Intermediate Similarity	NPC222011
0.7524	Intermediate Similarity	NPC114274
0.7523	Intermediate Similarity	NPC329048
0.7523	Intermediate Similarity	NPC330011
0.7522	Intermediate Similarity	NPC471398
0.7522	Intermediate Similarity	NPC474181
0.7521	Intermediate Similarity	NPC107493
0.75	Intermediate Similarity	NPC29152
0.75	Intermediate Similarity	NPC469528
0.75	Intermediate Similarity	NPC38350
0.75	Intermediate Similarity	NPC278459
0.75	Intermediate Similarity	NPC228669
0.75	Intermediate Similarity	NPC44963
0.75	Intermediate Similarity	NPC137657
0.75	Intermediate Similarity	NPC213366
0.75	Intermediate Similarity	NPC164835

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 NPC475867 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1821
0.2-0.3	4103
0.3-0.4	2078
0.4-0.5	542
0.5-0.6	200
0.6-0.7	127
0.7-0.8	107
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7944	Intermediate Similarity	NPD7320	Approved
0.7941	Intermediate Similarity	NPD6084	Phase 2
0.7941	Intermediate Similarity	NPD6083	Phase 2
0.7921	Intermediate Similarity	NPD5695	Phase 3
0.7818	Intermediate Similarity	NPD8297	Approved
0.7778	Intermediate Similarity	NPD6080	Approved
0.7778	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD6904	Approved
0.7778	Intermediate Similarity	NPD6673	Approved
0.7778	Intermediate Similarity	NPD6899	Approved
0.7757	Intermediate Similarity	NPD5739	Approved
0.7757	Intermediate Similarity	NPD7128	Approved
0.7757	Intermediate Similarity	NPD6675	Approved
0.7757	Intermediate Similarity	NPD6402	Approved
0.7748	Intermediate Similarity	NPD4632	Approved
0.7732	Intermediate Similarity	NPD5329	Approved
0.7692	Intermediate Similarity	NPD5696	Approved
0.7685	Intermediate Similarity	NPD5697	Approved
0.7677	Intermediate Similarity	NPD6672	Approved
0.7677	Intermediate Similarity	NPD5737	Approved
0.7653	Intermediate Similarity	NPD5690	Phase 2
0.7652	Intermediate Similarity	NPD6319	Approved
0.7636	Intermediate Similarity	NPD7102	Approved
0.7636	Intermediate Similarity	NPD6883	Approved
0.7636	Intermediate Similarity	NPD7290	Approved
0.7629	Intermediate Similarity	NPD4197	Approved
0.7624	Intermediate Similarity	NPD6050	Approved
0.7615	Intermediate Similarity	NPD6011	Approved
0.76	Intermediate Similarity	NPD4753	Phase 2
0.7568	Intermediate Similarity	NPD6869	Approved
0.7568	Intermediate Similarity	NPD6649	Approved
0.7568	Intermediate Similarity	NPD6847	Approved
0.7568	Intermediate Similarity	NPD8130	Phase 1
0.7568	Intermediate Similarity	NPD6617	Approved
0.7568	Intermediate Similarity	NPD6650	Approved
0.7563	Intermediate Similarity	NPD7078	Approved
0.7545	Intermediate Similarity	NPD6012	Approved
0.7545	Intermediate Similarity	NPD6014	Approved
0.7545	Intermediate Similarity	NPD6372	Approved
0.7545	Intermediate Similarity	NPD6373	Approved
0.7545	Intermediate Similarity	NPD6013	Approved
0.7542	Intermediate Similarity	NPD7492	Approved
0.7525	Intermediate Similarity	NPD5692	Phase 3
0.7523	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7479	Intermediate Similarity	NPD6616	Approved
0.7477	Intermediate Similarity	NPD4634	Approved
0.7475	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6098	Approved
0.7475	Intermediate Similarity	NPD5280	Approved
0.7475	Intermediate Similarity	NPD4694	Approved
0.7453	Intermediate Similarity	NPD5285	Approved
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD5693	Phase 1
0.7451	Intermediate Similarity	NPD5281	Approved
0.7451	Intermediate Similarity	NPD5284	Approved
0.7451	Intermediate Similarity	NPD5694	Approved
0.7429	Intermediate Similarity	NPD4755	Approved
0.7423	Intermediate Similarity	NPD4223	Phase 3
0.7423	Intermediate Similarity	NPD4221	Approved
0.7411	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5210	Approved
0.7404	Intermediate Similarity	NPD4629	Approved
0.7404	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6009	Approved
0.7391	Intermediate Similarity	NPD7115	Discovery
0.7383	Intermediate Similarity	NPD5223	Approved
0.7379	Intermediate Similarity	NPD6399	Phase 3
0.7373	Intermediate Similarity	NPD6370	Approved
0.7355	Intermediate Similarity	NPD7736	Approved
0.735	Intermediate Similarity	NPD6059	Approved
0.7333	Intermediate Similarity	NPD5221	Approved
0.7333	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5226	Approved
0.7315	Intermediate Similarity	NPD5225	Approved
0.7315	Intermediate Similarity	NPD4633	Approved
0.7315	Intermediate Similarity	NPD5224	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.73	Intermediate Similarity	NPD6684	Approved
0.73	Intermediate Similarity	NPD7334	Approved
0.73	Intermediate Similarity	NPD7521	Approved
0.73	Intermediate Similarity	NPD6409	Approved
0.73	Intermediate Similarity	NPD7146	Approved
0.73	Intermediate Similarity	NPD5330	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.7288	Intermediate Similarity	NPD6016	Approved
0.7288	Intermediate Similarity	NPD6015	Approved
0.7282	Intermediate Similarity	NPD6079	Approved
0.7273	Intermediate Similarity	NPD8293	Discontinued
0.7264	Intermediate Similarity	NPD5173	Approved
0.7255	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5328	Approved
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7238	Intermediate Similarity	NPD5654	Approved
0.7227	Intermediate Similarity	NPD5988	Approved
0.7216	Intermediate Similarity	NPD4695	Discontinued
0.7188	Intermediate Similarity	NPD3617	Approved
0.7184	Intermediate Similarity	NPD5207	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7179	Intermediate Similarity	NPD6335	Approved
0.717	Intermediate Similarity	NPD4697	Phase 3
0.7167	Intermediate Similarity	NPD7604	Phase 2
0.7157	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5208	Approved
0.7155	Intermediate Similarity	NPD6274	Approved
0.7143	Intermediate Similarity	NPD5983	Phase 2
0.7129	Intermediate Similarity	NPD4138	Approved
0.7129	Intermediate Similarity	NPD4693	Phase 3
0.7129	Intermediate Similarity	NPD5279	Phase 3
0.7129	Intermediate Similarity	NPD5205	Approved
0.7129	Intermediate Similarity	NPD4689	Approved
0.7129	Intermediate Similarity	NPD4690	Approved
0.7129	Intermediate Similarity	NPD4688	Approved
0.7119	Intermediate Similarity	NPD7100	Approved
0.7119	Intermediate Similarity	NPD7101	Approved
0.7117	Intermediate Similarity	NPD6008	Approved
0.7103	Intermediate Similarity	NPD5959	Approved
0.71	Intermediate Similarity	NPD3665	Phase 1
0.71	Intermediate Similarity	NPD3133	Approved
0.71	Intermediate Similarity	NPD4786	Approved
0.71	Intermediate Similarity	NPD3666	Approved
0.7094	Intermediate Similarity	NPD6317	Approved
0.7091	Intermediate Similarity	NPD4754	Approved
0.7049	Intermediate Similarity	NPD6336	Discontinued
0.7048	Intermediate Similarity	NPD5133	Approved
0.7034	Intermediate Similarity	NPD6313	Approved
0.7034	Intermediate Similarity	NPD6314	Approved
0.7009	Intermediate Similarity	NPD6868	Approved
0.7	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4730	Approved
0.6991	Remote Similarity	NPD4729	Approved
0.6991	Remote Similarity	NPD5128	Approved
0.6981	Remote Similarity	NPD6001	Approved
0.6964	Remote Similarity	NPD4768	Approved
0.6964	Remote Similarity	NPD4767	Approved
0.6939	Remote Similarity	NPD4195	Approved
0.6935	Remote Similarity	NPD6033	Approved
0.6903	Remote Similarity	NPD6614	Approved
0.6903	Remote Similarity	NPD6412	Phase 2
0.69	Remote Similarity	NPD3667	Approved
0.69	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6053	Discontinued
0.6893	Remote Similarity	NPD3573	Approved
0.6887	Remote Similarity	NPD4202	Approved
0.687	Remote Similarity	NPD5250	Approved
0.687	Remote Similarity	NPD5135	Approved
0.687	Remote Similarity	NPD5251	Approved
0.687	Remote Similarity	NPD5248	Approved
0.687	Remote Similarity	NPD5169	Approved
0.687	Remote Similarity	NPD5249	Phase 3
0.687	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5247	Approved
0.686	Remote Similarity	NPD6908	Approved
0.686	Remote Similarity	NPD6909	Approved
0.6857	Remote Similarity	NPD5785	Approved
0.6847	Remote Similarity	NPD5091	Approved
0.6832	Remote Similarity	NPD4788	Approved
0.6822	Remote Similarity	NPD7748	Approved
0.681	Remote Similarity	NPD5217	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.681	Remote Similarity	NPD5127	Approved
0.68	Remote Similarity	NPD4692	Approved
0.68	Remote Similarity	NPD4139	Approved
0.68	Remote Similarity	NPD5369	Approved
0.6796	Remote Similarity	NPD3618	Phase 1
0.6792	Remote Similarity	NPD6411	Approved
0.6792	Remote Similarity	NPD7515	Phase 2
0.6786	Remote Similarity	NPD6052	Approved
0.6754	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7319	Approved
0.6727	Remote Similarity	NPD4225	Approved
0.6699	Remote Similarity	NPD5363	Approved
0.6698	Remote Similarity	NPD4096	Approved
0.6697	Remote Similarity	NPD7614	Phase 1
0.6696	Remote Similarity	NPD5168	Approved
0.6694	Remote Similarity	NPD4522	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.664	Remote Similarity	NPD7507	Approved
0.6639	Remote Similarity	NPD5167	Approved
0.6636	Remote Similarity	NPD7902	Approved
0.6635	Remote Similarity	NPD5786	Approved
0.6613	Remote Similarity	NPD8328	Phase 3
0.6606	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6101	Approved
0.6602	Remote Similarity	NPD3668	Phase 3
0.6581	Remote Similarity	NPD6371	Approved
0.6577	Remote Similarity	NPD7638	Approved
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5956	Approved
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7732	Phase 3
0.6518	Remote Similarity	NPD7639	Approved
0.6518	Remote Similarity	NPD7640	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