NPASS Compound

Structure

NPC471775 OpenBabel07101719152D 38 41 0 0 1 0 0 0 0 0999 V2000 -3.0137 -1.8182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4049 0.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8697 -2.7978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8935 -2.7978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2664 -3.6363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0137 -2.6934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1274 -0.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6332 -0.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9429 0.2527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2093 -0.6226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2664 -0.8752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0952 -0.1173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5761 -0.1850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8996 -1.3128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6908 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.2270 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6469 -2.2558 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3816 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9567 -2.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 2 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 -7.0381 0.1354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8288 0.7580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 -1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8425 -1.0602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8996 -3.1987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 31 1 0 0 0 0 10 11 2 0 0 0 0 10 24 1 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 32 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 19 1 1 6 0 0 0 19 21 1 0 0 0 0 20 33 2 0 0 0 0 20 37 1 0 0 0 0 21 34 2 0 0 0 0 22 18 1 1 0 0 0 22 37 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 30 1 0 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 35 2 0 0 0 0 26 32 1 0 0 0 0 26 36 2 0 0 0 0 27 22 1 6 0 0 0 27 29 1 0 0 0 0 27 38 1 0 0 0 0 29 38 1 0 0 0 0 30 7 1 6 0 0 0 31 32 1 6 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.35
Volume:	567.361
LogP:	3.804
LogD:	3.239
LogS:	-3.896
# Rotatable Bonds:	9
TPSA:	90.04
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	5.252
Fsp3:	0.812
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:	-5.122
MDCK Permeability:	2.0302208213252015e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.433
Plasma Protein Binding (PPB):	89.47286224365234%
Volume Distribution (VD):	1.192
Pgp-substrate:	8.384730339050293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.278
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.704
CYP3A4-substrate:	0.848

ADMET: Excretion

Clearance (CL):	5.553
Half-life (T1/2):	0.456

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.395
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.258
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.05
Carcinogencity:	0.907
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC471775

Natural Product ID:	NPC471775
*Common Name:**	[(1S,3R)-6-[(1R,4Bs,10As)-1,4B,8,8,10A-Pentamethyl-2,7-Dioxo-4A,5,6,8A,9,10-Hexahydrophenanthren-1-Yl]-1-[(2R)-3,3-Dimethyloxiran-2-Yl]-3-Methyl-4-Oxohexyl] Acetate
IUPAC Name:	[(1S,3R)-6-[(1R,4bS,10aS)-1,4b,8,8,10a-pentamethyl-2,7-dioxo-4a,5,6,8a,9,10-hexahydrophenanthren-1-yl]-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-methyl-4-oxohexyl] acetate
Synonyms:
Standard InCHIKey:	VBHJDRFDDJMSAD-ROJQKZBCSA-N
Standard InCHI:	InChI=1S/C32H48O6/c1-19(18-22(37-20(2)33)27-29(5,6)38-27)21(34)12-16-32(9)26(36)11-10-24-30(7)15-14-25(35)28(3,4)23(30)13-17-31(24,32)8/h10-11,19,22-24,27H,12-18H2,1-9H3/t19-,22+,23?,24?,27-,30+,31+,32+/m1/s1
SMILES:	CC(CC(C1C(O1)(C)C)OC(=O)C)C(=O)CCC2(C(=O)C=CC3C2(CCC4C3(CCC(=O)C4(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL319038
PubChem CID:	44335290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	2.9	%	PMID[464195]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	10.2	%	PMID[464195]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	22.7	%	PMID[464195]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	61.0	%	PMID[464195]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	113.8	%	PMID[464195]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	23000.0	nM	PMID[464195]

☑ 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 NPC471775 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	245
0.1-0.2	1531
0.2-0.3	5950
0.3-0.4	12526
0.4-0.5	9423
0.5-0.6	7251
0.6-0.7	5102
0.7-0.8	661
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC471582
0.83	Intermediate Similarity	NPC473163
0.8125	Intermediate Similarity	NPC218301
0.8105	Intermediate Similarity	NPC469546
0.81	Intermediate Similarity	NPC475385
0.81	Intermediate Similarity	NPC475392
0.81	Intermediate Similarity	NPC475202
0.8081	Intermediate Similarity	NPC226986
0.8061	Intermediate Similarity	NPC274417
0.8041	Intermediate Similarity	NPC79117
0.802	Intermediate Similarity	NPC476213
0.802	Intermediate Similarity	NPC476246
0.802	Intermediate Similarity	NPC477871
0.802	Intermediate Similarity	NPC477870
0.8	Intermediate Similarity	NPC474242
0.798	Intermediate Similarity	NPC111684
0.798	Intermediate Similarity	NPC58052
0.7961	Intermediate Similarity	NPC228669
0.7961	Intermediate Similarity	NPC255309
0.7961	Intermediate Similarity	NPC164835
0.7959	Intermediate Similarity	NPC294266
0.7959	Intermediate Similarity	NPC269729
0.7941	Intermediate Similarity	NPC308351
0.7941	Intermediate Similarity	NPC271266
0.7941	Intermediate Similarity	NPC476126
0.7941	Intermediate Similarity	NPC476235
0.7925	Intermediate Similarity	NPC253906
0.79	Intermediate Similarity	NPC292133
0.79	Intermediate Similarity	NPC23680
0.79	Intermediate Similarity	NPC473456
0.7895	Intermediate Similarity	NPC30421
0.789	Intermediate Similarity	NPC270929
0.7885	Intermediate Similarity	NPC96377
0.7864	Intermediate Similarity	NPC264048
0.7857	Intermediate Similarity	NPC469315
0.7857	Intermediate Similarity	NPC476416
0.785	Intermediate Similarity	NPC470960
0.7843	Intermediate Similarity	NPC101067
0.7843	Intermediate Similarity	NPC469327
0.7843	Intermediate Similarity	NPC476134
0.7835	Intermediate Similarity	NPC476369
0.7835	Intermediate Similarity	NPC476437
0.7835	Intermediate Similarity	NPC328141
0.783	Intermediate Similarity	NPC41405
0.7826	Intermediate Similarity	NPC474955
0.7802	Intermediate Similarity	NPC476177
0.78	Intermediate Similarity	NPC473164
0.7789	Intermediate Similarity	NPC220478
0.7789	Intermediate Similarity	NPC195640
0.7778	Intermediate Similarity	NPC476415
0.7778	Intermediate Similarity	NPC56525
0.7778	Intermediate Similarity	NPC472300
0.7767	Intermediate Similarity	NPC473928
0.7757	Intermediate Similarity	NPC5284
0.7757	Intermediate Similarity	NPC473627
0.7755	Intermediate Similarity	NPC230064
0.7748	Intermediate Similarity	NPC329736
0.7748	Intermediate Similarity	NPC473720
0.7745	Intermediate Similarity	NPC472728
0.7745	Intermediate Similarity	NPC472727
0.7742	Intermediate Similarity	NPC302661
0.7742	Intermediate Similarity	NPC238991
0.7742	Intermediate Similarity	NPC100297
0.7736	Intermediate Similarity	NPC470269
0.7727	Intermediate Similarity	NPC243981
0.7723	Intermediate Similarity	NPC124246
0.7723	Intermediate Similarity	NPC38530
0.7723	Intermediate Similarity	NPC84335
0.7717	Intermediate Similarity	NPC474956
0.7714	Intermediate Similarity	NPC470267
0.7714	Intermediate Similarity	NPC181265
0.7708	Intermediate Similarity	NPC476409
0.7692	Intermediate Similarity	NPC470954
0.7692	Intermediate Similarity	NPC239716
0.7685	Intermediate Similarity	NPC470246
0.7684	Intermediate Similarity	NPC323765
0.7684	Intermediate Similarity	NPC2709
0.7679	Intermediate Similarity	NPC61520
0.7679	Intermediate Similarity	NPC475520
0.767	Intermediate Similarity	NPC310981
0.767	Intermediate Similarity	NPC115862
0.7664	Intermediate Similarity	NPC310546
0.7664	Intermediate Similarity	NPC241927
0.7664	Intermediate Similarity	NPC469370
0.7664	Intermediate Similarity	NPC258543
0.766	Intermediate Similarity	NPC108045
0.766	Intermediate Similarity	NPC475622
0.7653	Intermediate Similarity	NPC475965
0.7653	Intermediate Similarity	NPC474842
0.7647	Intermediate Similarity	NPC153776
0.7647	Intermediate Similarity	NPC472729
0.7647	Intermediate Similarity	NPC177680
0.7647	Intermediate Similarity	NPC472730
0.7647	Intermediate Similarity	NPC176845
0.7642	Intermediate Similarity	NPC475294
0.7642	Intermediate Similarity	NPC471601
0.7634	Intermediate Similarity	NPC327002
0.7634	Intermediate Similarity	NPC278459
0.7624	Intermediate Similarity	NPC471822
0.7624	Intermediate Similarity	NPC21681
0.7624	Intermediate Similarity	NPC472675
0.7619	Intermediate Similarity	NPC189616
0.7619	Intermediate Similarity	NPC235889
0.7619	Intermediate Similarity	NPC470104
0.7615	Intermediate Similarity	NPC234042
0.7615	Intermediate Similarity	NPC100267
0.7615	Intermediate Similarity	NPC264634
0.7615	Intermediate Similarity	NPC147180
0.7615	Intermediate Similarity	NPC475524
0.7615	Intermediate Similarity	NPC152117
0.7604	Intermediate Similarity	NPC264127
0.7604	Intermediate Similarity	NPC471042
0.76	Intermediate Similarity	NPC473172
0.76	Intermediate Similarity	NPC38830
0.76	Intermediate Similarity	NPC473431
0.76	Intermediate Similarity	NPC67831
0.76	Intermediate Similarity	NPC473280
0.76	Intermediate Similarity	NPC471078
0.76	Intermediate Similarity	NPC318332
0.76	Intermediate Similarity	NPC174051
0.76	Intermediate Similarity	NPC473435
0.76	Intermediate Similarity	NPC74751
0.7596	Intermediate Similarity	NPC283567
0.7593	Intermediate Similarity	NPC37116
0.7593	Intermediate Similarity	NPC239097
0.7579	Intermediate Similarity	NPC475193
0.7579	Intermediate Similarity	NPC312660
0.7579	Intermediate Similarity	NPC120158
0.7576	Intermediate Similarity	NPC252433
0.7576	Intermediate Similarity	NPC262870
0.7573	Intermediate Similarity	NPC287833
0.7573	Intermediate Similarity	NPC167974
0.7551	Intermediate Similarity	NPC477973
0.7551	Intermediate Similarity	NPC473039
0.7551	Intermediate Similarity	NPC284561
0.7549	Intermediate Similarity	NPC170131
0.7549	Intermediate Similarity	NPC26413
0.7549	Intermediate Similarity	NPC472731
0.7549	Intermediate Similarity	NPC472732
0.7547	Intermediate Similarity	NPC292588
0.7545	Intermediate Similarity	NPC255017
0.7545	Intermediate Similarity	NPC198539
0.7544	Intermediate Similarity	NPC204731
0.7544	Intermediate Similarity	NPC310511
0.7526	Intermediate Similarity	NPC38885
0.7526	Intermediate Similarity	NPC46912
0.7526	Intermediate Similarity	NPC162107
0.7525	Intermediate Similarity	NPC33473
0.7524	Intermediate Similarity	NPC275583
0.7524	Intermediate Similarity	NPC282233
0.7524	Intermediate Similarity	NPC95585
0.7524	Intermediate Similarity	NPC478057
0.7524	Intermediate Similarity	NPC475321
0.7523	Intermediate Similarity	NPC214797
0.7523	Intermediate Similarity	NPC474229
0.7523	Intermediate Similarity	NPC118860
0.7523	Intermediate Similarity	NPC231589
0.7522	Intermediate Similarity	NPC161065
0.7522	Intermediate Similarity	NPC473203
0.75	Intermediate Similarity	NPC312824
0.75	Intermediate Similarity	NPC183580
0.75	Intermediate Similarity	NPC250018
0.75	Intermediate Similarity	NPC189311
0.75	Intermediate Similarity	NPC476223
0.75	Intermediate Similarity	NPC470223
0.75	Intermediate Similarity	NPC477615
0.75	Intermediate Similarity	NPC471854
0.75	Intermediate Similarity	NPC167606
0.75	Intermediate Similarity	NPC474185
0.75	Intermediate Similarity	NPC470492
0.75	Intermediate Similarity	NPC224720
0.75	Intermediate Similarity	NPC131840
0.75	Intermediate Similarity	NPC476240
0.75	Intermediate Similarity	NPC20302
0.75	Intermediate Similarity	NPC140055
0.75	Intermediate Similarity	NPC304495
0.75	Intermediate Similarity	NPC470493
0.75	Intermediate Similarity	NPC286528
0.7478	Intermediate Similarity	NPC170538
0.7477	Intermediate Similarity	NPC133422
0.7477	Intermediate Similarity	NPC180744
0.7477	Intermediate Similarity	NPC44063
0.7477	Intermediate Similarity	NPC471783
0.7477	Intermediate Similarity	NPC220974
0.7477	Intermediate Similarity	NPC9457
0.7476	Intermediate Similarity	NPC471331
0.7476	Intermediate Similarity	NPC472687
0.7476	Intermediate Similarity	NPC478056
0.7476	Intermediate Similarity	NPC471966
0.7476	Intermediate Similarity	NPC275439
0.7476	Intermediate Similarity	NPC203388
0.7476	Intermediate Similarity	NPC99657
0.7476	Intermediate Similarity	NPC471330
0.7476	Intermediate Similarity	NPC112753
0.7475	Intermediate Similarity	NPC152467
0.7475	Intermediate Similarity	NPC214844
0.7475	Intermediate Similarity	NPC159748
0.7475	Intermediate Similarity	NPC101651
0.7475	Intermediate Similarity	NPC471818
0.7474	Intermediate Similarity	NPC102197

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 NPC471775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	1857
0.2-0.3	4043
0.3-0.4	2012
0.4-0.5	598
0.5-0.6	214
0.6-0.7	147
0.7-0.8	57
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
0.7895	Intermediate Similarity	NPD3573	Approved
0.7789	Intermediate Similarity	NPD7334	Approved
0.7789	Intermediate Similarity	NPD7521	Approved
0.7789	Intermediate Similarity	NPD6409	Approved
0.7789	Intermediate Similarity	NPD5330	Approved
0.7789	Intermediate Similarity	NPD7146	Approved
0.7789	Intermediate Similarity	NPD6684	Approved
0.7778	Intermediate Similarity	NPD7900	Approved
0.7778	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8297	Approved
0.7647	Intermediate Similarity	NPD5696	Approved
0.7629	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6903	Approved
0.7629	Intermediate Similarity	NPD5737	Approved
0.7629	Intermediate Similarity	NPD6672	Approved
0.76	Intermediate Similarity	NPD7748	Approved
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.7549	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD6008	Approved
0.7525	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD8130	Phase 1
0.7523	Intermediate Similarity	NPD6650	Approved
0.7523	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD5697	Approved
0.7451	Intermediate Similarity	NPD7732	Phase 3
0.7431	Intermediate Similarity	NPD7102	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD7128	Approved
0.7383	Intermediate Similarity	NPD5739	Approved
0.7383	Intermediate Similarity	NPD6675	Approved
0.7383	Intermediate Similarity	NPD6402	Approved
0.7379	Intermediate Similarity	NPD6083	Phase 2
0.7379	Intermediate Similarity	NPD6084	Phase 2
0.7374	Intermediate Similarity	NPD6080	Approved
0.7374	Intermediate Similarity	NPD6673	Approved
0.7374	Intermediate Similarity	NPD6904	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7364	Intermediate Similarity	NPD6617	Approved
0.7353	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5210	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6012	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7297	Intermediate Similarity	NPD6882	Approved
0.7248	Intermediate Similarity	NPD7320	Approved
0.7248	Intermediate Similarity	NPD6011	Approved
0.7228	Intermediate Similarity	NPD6079	Approved
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7188	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5695	Phase 3
0.7156	Intermediate Similarity	NPD6614	Approved
0.7156	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7129	Intermediate Similarity	NPD5207	Approved
0.71	Intermediate Similarity	NPD5208	Approved
0.7087	Intermediate Similarity	NPD6001	Approved
0.708	Intermediate Similarity	NPD4632	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7071	Intermediate Similarity	NPD6098	Approved
0.7059	Intermediate Similarity	NPD6050	Approved
0.7059	Intermediate Similarity	NPD5694	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD6411	Approved
0.703	Intermediate Similarity	NPD5328	Approved
0.7009	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7604	Phase 2
0.6961	Remote Similarity	NPD5692	Phase 3
0.6952	Remote Similarity	NPD7614	Phase 1
0.6952	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5222	Approved
0.6952	Remote Similarity	NPD5221	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD5224	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5211	Phase 2
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6903	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3618	Phase 1
0.6897	Remote Similarity	NPD6009	Approved
0.6893	Remote Similarity	NPD5281	Approved
0.6893	Remote Similarity	NPD5284	Approved
0.6887	Remote Similarity	NPD4755	Approved
0.6887	Remote Similarity	NPD5173	Approved
0.6885	Remote Similarity	NPD7736	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD3665	Phase 1
0.6869	Remote Similarity	NPD3666	Approved
0.6869	Remote Similarity	NPD3133	Approved
0.6864	Remote Similarity	NPD6054	Approved
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6101	Approved
0.6863	Remote Similarity	NPD4753	Phase 2
0.686	Remote Similarity	NPD6616	Approved
0.6852	Remote Similarity	NPD5223	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6838	Remote Similarity	NPD6335	Approved
0.6833	Remote Similarity	NPD8328	Phase 3
0.6818	Remote Similarity	NPD5141	Approved
0.6814	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6868	Approved
0.681	Remote Similarity	NPD6274	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6804	Remote Similarity	NPD4695	Discontinued
0.6803	Remote Similarity	NPD7078	Approved
0.6792	Remote Similarity	NPD4697	Phase 3
0.6786	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6686	Approved
0.6759	Remote Similarity	NPD4700	Approved
0.6752	Remote Similarity	NPD6317	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6052	Approved
0.6726	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6336	Discontinued
0.67	Remote Similarity	NPD3668	Phase 3
0.67	Remote Similarity	NPD4786	Approved
0.6699	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6314	Approved
0.6695	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6637	Remote Similarity	NPD4729	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6634	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5329	Approved
0.6612	Remote Similarity	NPD5988	Approved
0.6583	Remote Similarity	NPD6059	Approved
0.6579	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5959	Approved
0.6571	Remote Similarity	NPD8034	Phase 2
0.6571	Remote Similarity	NPD8035	Phase 2
0.6569	Remote Similarity	NPD4519	Discontinued
0.6569	Remote Similarity	NPD5690	Phase 2
0.6569	Remote Similarity	NPD4623	Approved
0.6559	Remote Similarity	NPD4691	Approved
0.6542	Remote Similarity	NPD5654	Approved
0.6542	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6051	Approved
0.6535	Remote Similarity	NPD4197	Approved
0.6529	Remote Similarity	NPD6909	Approved
0.6529	Remote Similarity	NPD6908	Approved
0.6526	Remote Similarity	NPD4058	Approved
0.6522	Remote Similarity	NPD5247	Approved
0.6522	Remote Similarity	NPD5250	Approved
0.6522	Remote Similarity	NPD5251	Approved
0.6522	Remote Similarity	NPD5249	Phase 3
0.6522	Remote Similarity	NPD5248	Approved
0.6514	Remote Similarity	NPD7638	Approved
0.6509	Remote Similarity	NPD5779	Approved
0.6509	Remote Similarity	NPD4202	Approved
0.6509	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD6435	Approved
0.6491	Remote Similarity	NPD5128	Approved
0.6486	Remote Similarity	NPD5091	Approved
0.6481	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD5217	Approved
0.6466	Remote Similarity	NPD5215	Approved
0.646	Remote Similarity	NPD4767	Approved
0.646	Remote Similarity	NPD4768	Approved
0.6458	Remote Similarity	NPD8039	Approved
0.6457	Remote Similarity	NPD7260	Phase 2
0.6455	Remote Similarity	NPD7639	Approved
0.6455	Remote Similarity	NPD7640	Approved
0.6452	Remote Similarity	NPD4137	Phase 3
0.6429	Remote Similarity	NPD4754	Approved
0.6408	Remote Similarity	NPD5205	Approved
0.6408	Remote Similarity	NPD4690	Approved
0.6408	Remote Similarity	NPD4689	Approved
0.6408	Remote Similarity	NPD5279	Phase 3
0.6408	Remote Similarity	NPD4693	Phase 3
0.6408	Remote Similarity	NPD4138	Approved
0.6408	Remote Similarity	NPD4688	Approved
0.6383	Remote Similarity	NPD4747	Approved
0.6379	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5169	Approved
0.6379	Remote Similarity	NPD5135	Approved
0.6364	Remote Similarity	NPD4195	Approved
0.6356	Remote Similarity	NPD7094	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