NPASS Compound

Structure

NPC471582 OpenBabel07101718272D 37 41 0 0 1 0 0 0 0 0999 V2000 -3.1789 0.6876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4758 -2.6201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8697 -1.1070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3578 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8414 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9129 1.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -2.4405 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 0.9708 0.1020 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 0.0000 -1.9524 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 2.5362 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8274 -0.9663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2030 0.9549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5257 -0.0379 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4307 -2.8231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1738 1.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7822 -1.1692 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 0.8454 -1.4643 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3816 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5709 0.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4354 -0.4438 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 -4.6384 0.5111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 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 -3.7324 -3.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6619 1.9023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 -3.4167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0839 -2.0976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3638 -0.1421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 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 20 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 17 32 1 0 0 0 0 18 1 1 1 0 0 0 18 26 1 0 0 0 0 19 33 2 0 0 0 0 19 36 1 0 0 0 0 20 26 2 0 0 0 0 20 32 1 0 0 0 0 21 26 1 0 0 0 0 21 34 2 0 0 0 0 22 16 1 6 0 0 0 22 36 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 27 22 1 1 0 0 0 27 29 1 0 0 0 0 27 37 1 0 0 0 0 29 37 1 0 0 0 0 30 7 1 1 0 0 0 31 32 1 1 0 0 0 32 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.33
Volume:	550.015
LogP:	5.119
LogD:	3.897
LogS:	-5.252
# Rotatable Bonds:	6
TPSA:	72.97
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	5.285
Fsp3:	0.781
Lipinski Rule-of-5:	Rejected
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:	-5.115
MDCK Permeability:	2.1299954823916778e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	93.84162139892578%
Volume Distribution (VD):	1.641
Pgp-substrate:	5.9451003074646%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.227
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.378
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	4.537
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.429
Human Hepatotoxicity (H-HT):	0.554
Drug-inuced Liver Injury (DILI):	0.37
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.173
Carcinogencity:	0.858
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC471582

Natural Product ID:	NPC471582
*Common Name:**	[(1S,3R)-1-[(2R)-3,3-Dimethyloxiran-2-Yl]-3-[(8S,10S,14R)-4,4,8,10,14-Pentamethyl-3,16-Dioxo-2,5,6,7,9,15-Hexahydro-1H-Cyclopenta[A]Phenanthren-17-Yl]Butyl] Acetate
IUPAC Name:	[(1S,3R)-1-[(2R)-3,3-dimethyloxiran-2-yl]-3-[(8S,10S,14R)-4,4,8,10,14-pentamethyl-3,16-dioxo-2,5,6,7,9,15-hexahydro-1H-cyclopenta[a]phenanthren-17-yl]butyl] acetate
Synonyms:
Standard InCHIKey:	ARRUGSBFWQZLTR-BGTPOSJASA-N
Standard InCHI:	InChI=1S/C32H46O5/c1-18(16-22(36-19(2)33)27-29(5,6)37-27)26-20-10-11-24-30(7)14-13-25(35)28(3,4)23(30)12-15-31(24,8)32(20,9)17-21(26)34/h10-11,18,22-24,27H,12-17H2,1-9H3/t18-,22+,23?,24?,27-,30+,31+,32+/m1/s1
SMILES:	CC(CC(C1C(O1)(C)C)OC(=O)C)C2=C3C=CC4C5(CCC(=O)C(C5CCC4(C3(CC2=O)C)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL262708
PubChem CID:	44335344
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	=	17.8	%	PMID[536859]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	27.9	%	PMID[536859]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	54.8	%	PMID[536859]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	86.5	%	PMID[536859]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	104.0	%	PMID[536859]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	8400.0	nM	PMID[536859]

☑ 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 NPC471582 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	233
0.1-0.2	1181
0.2-0.3	4885
0.3-0.4	11417
0.4-0.5	11081
0.5-0.6	7482
0.6-0.7	5551
0.7-0.8	850
0.8-0.85	14
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9271	High Similarity	NPC473163
0.8947	High Similarity	NPC471775
0.8542	High Similarity	NPC473172
0.8438	Intermediate Similarity	NPC79117
0.8438	Intermediate Similarity	NPC469315
0.84	Intermediate Similarity	NPC469327
0.8367	Intermediate Similarity	NPC473164
0.8351	Intermediate Similarity	NPC473431
0.8351	Intermediate Similarity	NPC471078
0.8351	Intermediate Similarity	NPC473435
0.8351	Intermediate Similarity	NPC473280
0.8333	Intermediate Similarity	NPC218301
0.8333	Intermediate Similarity	NPC473175
0.8229	Intermediate Similarity	NPC474842
0.8229	Intermediate Similarity	NPC475965
0.8211	Intermediate Similarity	NPC472220
0.8211	Intermediate Similarity	NPC97884
0.8191	Intermediate Similarity	NPC195640
0.819	Intermediate Similarity	NPC41405
0.8182	Intermediate Similarity	NPC58052
0.8182	Intermediate Similarity	NPC111684
0.8182	Intermediate Similarity	NPC471822
0.8137	Intermediate Similarity	NPC308351
0.8137	Intermediate Similarity	NPC271266
0.8137	Intermediate Similarity	NPC473928
0.8113	Intermediate Similarity	NPC5284
0.81	Intermediate Similarity	NPC292133
0.81	Intermediate Similarity	NPC110937
0.8085	Intermediate Similarity	NPC323765
0.8073	Intermediate Similarity	NPC243981
0.8065	Intermediate Similarity	NPC108045
0.8065	Intermediate Similarity	NPC475622
0.8058	Intermediate Similarity	NPC264048
0.8043	Intermediate Similarity	NPC474955
0.8	Intermediate Similarity	NPC122324
0.8	Intermediate Similarity	NPC151725
0.8	Intermediate Similarity	NPC9457
0.8	Intermediate Similarity	NPC471777
0.8	Intermediate Similarity	NPC264127
0.8	Intermediate Similarity	NPC471783
0.8	Intermediate Similarity	NPC106425
0.7981	Intermediate Similarity	NPC228669
0.7981	Intermediate Similarity	NPC255309
0.7981	Intermediate Similarity	NPC164835
0.798	Intermediate Similarity	NPC38830
0.798	Intermediate Similarity	NPC174051
0.798	Intermediate Similarity	NPC473162
0.798	Intermediate Similarity	NPC56525
0.798	Intermediate Similarity	NPC67831
0.7963	Intermediate Similarity	NPC234042
0.7963	Intermediate Similarity	NPC152117
0.7961	Intermediate Similarity	NPC320447
0.7959	Intermediate Similarity	NPC262870
0.7941	Intermediate Similarity	NPC167974
0.7938	Intermediate Similarity	NPC284561
0.7925	Intermediate Similarity	NPC473482
0.7925	Intermediate Similarity	NPC475418
0.7925	Intermediate Similarity	NPC318363
0.7905	Intermediate Similarity	NPC470267
0.7905	Intermediate Similarity	NPC181265
0.7905	Intermediate Similarity	NPC469874
0.7905	Intermediate Similarity	NPC96377
0.79	Intermediate Similarity	NPC473170
0.789	Intermediate Similarity	NPC255017
0.7885	Intermediate Similarity	NPC475526
0.7885	Intermediate Similarity	NPC473283
0.7885	Intermediate Similarity	NPC329345
0.7885	Intermediate Similarity	NPC470954
0.7885	Intermediate Similarity	NPC72151
0.7876	Intermediate Similarity	NPC204731
0.787	Intermediate Similarity	NPC470960
0.7864	Intermediate Similarity	NPC115899
0.7864	Intermediate Similarity	NPC310981
0.7864	Intermediate Similarity	NPC473174
0.7864	Intermediate Similarity	NPC168319
0.7864	Intermediate Similarity	NPC194028
0.7857	Intermediate Similarity	NPC161065
0.785	Intermediate Similarity	NPC474242
0.785	Intermediate Similarity	NPC475065
0.7843	Intermediate Similarity	NPC471717
0.783	Intermediate Similarity	NPC473284
0.783	Intermediate Similarity	NPC471601
0.783	Intermediate Similarity	NPC475294
0.7822	Intermediate Similarity	NPC471153
0.7822	Intermediate Similarity	NPC471039
0.7812	Intermediate Similarity	NPC220478
0.781	Intermediate Similarity	NPC235889
0.781	Intermediate Similarity	NPC189616
0.7802	Intermediate Similarity	NPC472300
0.78	Intermediate Similarity	NPC159410
0.78	Intermediate Similarity	NPC294266
0.78	Intermediate Similarity	NPC471040
0.7788	Intermediate Similarity	NPC241192
0.7788	Intermediate Similarity	NPC114540
0.7788	Intermediate Similarity	NPC155332
0.7788	Intermediate Similarity	NPC32577
0.7778	Intermediate Similarity	NPC473986
0.7778	Intermediate Similarity	NPC253906
0.7778	Intermediate Similarity	NPC474018
0.7778	Intermediate Similarity	NPC239097
0.7778	Intermediate Similarity	NPC473627
0.7767	Intermediate Similarity	NPC475202
0.7767	Intermediate Similarity	NPC266955
0.7767	Intermediate Similarity	NPC475385
0.7767	Intermediate Similarity	NPC35751
0.7767	Intermediate Similarity	NPC475392
0.7766	Intermediate Similarity	NPC100297
0.7757	Intermediate Similarity	NPC470269
0.7755	Intermediate Similarity	NPC305039
0.7755	Intermediate Similarity	NPC475049
0.7755	Intermediate Similarity	NPC474570
0.7748	Intermediate Similarity	NPC270929
0.7745	Intermediate Similarity	NPC473456
0.7745	Intermediate Similarity	NPC23680
0.7745	Intermediate Similarity	NPC38530
0.7745	Intermediate Similarity	NPC2049
0.7745	Intermediate Similarity	NPC84335
0.7745	Intermediate Similarity	NPC473161
0.7732	Intermediate Similarity	NPC469322
0.7732	Intermediate Similarity	NPC30421
0.7723	Intermediate Similarity	NPC33473
0.7723	Intermediate Similarity	NPC469329
0.7723	Intermediate Similarity	NPC171395
0.7723	Intermediate Similarity	NPC274417
0.7723	Intermediate Similarity	NPC88310
0.7723	Intermediate Similarity	NPC30677
0.7723	Intermediate Similarity	NPC139459
0.7723	Intermediate Similarity	NPC37787
0.7723	Intermediate Similarity	NPC473415
0.7723	Intermediate Similarity	NPC180557
0.7717	Intermediate Similarity	NPC4827
0.7708	Intermediate Similarity	NPC470223
0.7708	Intermediate Similarity	NPC76333
0.7706	Intermediate Similarity	NPC474229
0.77	Intermediate Similarity	NPC474185
0.7699	Intermediate Similarity	NPC475520
0.7692	Intermediate Similarity	NPC99411
0.7685	Intermediate Similarity	NPC469370
0.7685	Intermediate Similarity	NPC258543
0.7685	Intermediate Similarity	NPC241927
0.7679	Intermediate Similarity	NPC183580
0.7679	Intermediate Similarity	NPC312824
0.7679	Intermediate Similarity	NPC470493
0.7677	Intermediate Similarity	NPC220454
0.7677	Intermediate Similarity	NPC328141
0.7677	Intermediate Similarity	NPC212679
0.7677	Intermediate Similarity	NPC471896
0.7677	Intermediate Similarity	NPC469595
0.767	Intermediate Similarity	NPC176845
0.7664	Intermediate Similarity	NPC330011
0.7664	Intermediate Similarity	NPC473169
0.7664	Intermediate Similarity	NPC44063
0.7664	Intermediate Similarity	NPC220974
0.7664	Intermediate Similarity	NPC476958
0.7664	Intermediate Similarity	NPC329048
0.766	Intermediate Similarity	NPC327002
0.7653	Intermediate Similarity	NPC472302
0.7653	Intermediate Similarity	NPC28227
0.7647	Intermediate Similarity	NPC322063
0.7642	Intermediate Similarity	NPC471293
0.7636	Intermediate Similarity	NPC100267
0.7636	Intermediate Similarity	NPC475524
0.7634	Intermediate Similarity	NPC476177
0.7624	Intermediate Similarity	NPC74751
0.7624	Intermediate Similarity	NPC318332
0.7624	Intermediate Similarity	NPC124207
0.7624	Intermediate Similarity	NPC240617
0.7624	Intermediate Similarity	NPC269729
0.7624	Intermediate Similarity	NPC49670
0.7619	Intermediate Similarity	NPC22388
0.7619	Intermediate Similarity	NPC469316
0.7615	Intermediate Similarity	NPC37116
0.7615	Intermediate Similarity	NPC29133
0.7611	Intermediate Similarity	NPC329736
0.7611	Intermediate Similarity	NPC473720
0.7604	Intermediate Similarity	NPC109512
0.7604	Intermediate Similarity	NPC100391
0.7604	Intermediate Similarity	NPC120158
0.7604	Intermediate Similarity	NPC312660
0.7604	Intermediate Similarity	NPC475193
0.76	Intermediate Similarity	NPC204341
0.76	Intermediate Similarity	NPC19114
0.7596	Intermediate Similarity	NPC471041
0.7593	Intermediate Similarity	NPC220155
0.7589	Intermediate Similarity	NPC302471
0.7579	Intermediate Similarity	NPC142683
0.7579	Intermediate Similarity	NPC327969
0.7579	Intermediate Similarity	NPC240302
0.7579	Intermediate Similarity	NPC321289
0.7576	Intermediate Similarity	NPC177141
0.7576	Intermediate Similarity	NPC474844
0.7576	Intermediate Similarity	NPC469323
0.7576	Intermediate Similarity	NPC469546
0.7576	Intermediate Similarity	NPC262043
0.7573	Intermediate Similarity	NPC472732
0.7573	Intermediate Similarity	NPC226986
0.7573	Intermediate Similarity	NPC472731
0.7573	Intermediate Similarity	NPC26413
0.7573	Intermediate Similarity	NPC151488
0.757	Intermediate Similarity	NPC470587

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 NPC471582 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1378
0.2-0.3	3940
0.3-0.4	2367
0.4-0.5	815
0.5-0.6	216
0.6-0.7	162
0.7-0.8	72
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
0.8191	Intermediate Similarity	NPD5330	Approved
0.8191	Intermediate Similarity	NPD6409	Approved
0.8191	Intermediate Similarity	NPD7334	Approved
0.8191	Intermediate Similarity	NPD6684	Approved
0.8191	Intermediate Similarity	NPD7521	Approved
0.8191	Intermediate Similarity	NPD7146	Approved
0.8021	Intermediate Similarity	NPD6672	Approved
0.8021	Intermediate Similarity	NPD5737	Approved
0.8021	Intermediate Similarity	NPD6903	Approved
0.8021	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD8297	Approved
0.7778	Intermediate Similarity	NPD6050	Approved
0.7778	Intermediate Similarity	NPD5694	Approved
0.7757	Intermediate Similarity	NPD6899	Approved
0.7757	Intermediate Similarity	NPD6881	Approved
0.7755	Intermediate Similarity	NPD6904	Approved
0.7755	Intermediate Similarity	NPD6673	Approved
0.7755	Intermediate Similarity	NPD6080	Approved
0.7745	Intermediate Similarity	NPD6084	Phase 2
0.7745	Intermediate Similarity	NPD6083	Phase 2
0.7736	Intermediate Similarity	NPD6675	Approved
0.7736	Intermediate Similarity	NPD7128	Approved
0.7736	Intermediate Similarity	NPD6402	Approved
0.7736	Intermediate Similarity	NPD5739	Approved
0.7736	Intermediate Similarity	NPD6008	Approved
0.7732	Intermediate Similarity	NPD3573	Approved
0.7723	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD8130	Phase 1
0.7677	Intermediate Similarity	NPD5207	Approved
0.7677	Intermediate Similarity	NPD5692	Phase 3
0.7664	Intermediate Similarity	NPD5697	Approved
0.7624	Intermediate Similarity	NPD7900	Approved
0.7624	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7748	Approved
0.7615	Intermediate Similarity	NPD6883	Approved
0.7615	Intermediate Similarity	NPD7290	Approved
0.7615	Intermediate Similarity	NPD7102	Approved
0.7593	Intermediate Similarity	NPD7320	Approved
0.7549	Intermediate Similarity	NPD5695	Phase 3
0.7545	Intermediate Similarity	NPD6617	Approved
0.7545	Intermediate Similarity	NPD6650	Approved
0.7545	Intermediate Similarity	NPD6869	Approved
0.7545	Intermediate Similarity	NPD6649	Approved
0.7545	Intermediate Similarity	NPD6847	Approved
0.7525	Intermediate Similarity	NPD6399	Phase 3
0.7523	Intermediate Similarity	NPD6372	Approved
0.7523	Intermediate Similarity	NPD6373	Approved
0.7523	Intermediate Similarity	NPD6013	Approved
0.7523	Intermediate Similarity	NPD6014	Approved
0.7523	Intermediate Similarity	NPD6012	Approved
0.7522	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD5696	Approved
0.7477	Intermediate Similarity	NPD6882	Approved
0.7475	Intermediate Similarity	NPD5208	Approved
0.7449	Intermediate Similarity	NPD6098	Approved
0.7431	Intermediate Similarity	NPD6011	Approved
0.7426	Intermediate Similarity	NPD5693	Phase 1
0.7426	Intermediate Similarity	NPD6079	Approved
0.7426	Intermediate Similarity	NPD6411	Approved
0.7426	Intermediate Similarity	NPD5284	Approved
0.7426	Intermediate Similarity	NPD5281	Approved
0.7404	Intermediate Similarity	NPD7902	Approved
0.74	Intermediate Similarity	NPD5328	Approved
0.7282	Intermediate Similarity	NPD6001	Approved
0.7264	Intermediate Similarity	NPD5286	Approved
0.7264	Intermediate Similarity	NPD4696	Approved
0.7264	Intermediate Similarity	NPD5285	Approved
0.7257	Intermediate Similarity	NPD4632	Approved
0.7255	Intermediate Similarity	NPD7515	Phase 2
0.7245	Intermediate Similarity	NPD3133	Approved
0.7245	Intermediate Similarity	NPD3665	Phase 1
0.7245	Intermediate Similarity	NPD3666	Approved
0.7238	Intermediate Similarity	NPD5959	Approved
0.7238	Intermediate Similarity	NPD4755	Approved
0.7232	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6101	Approved
0.7228	Intermediate Similarity	NPD4753	Phase 2
0.7216	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5654	Approved
0.7182	Intermediate Similarity	NPD6412	Phase 2
0.7179	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5225	Approved
0.713	Intermediate Similarity	NPD4633	Approved
0.713	Intermediate Similarity	NPD5226	Approved
0.713	Intermediate Similarity	NPD5211	Phase 2
0.713	Intermediate Similarity	NPD5224	Approved
0.7103	Intermediate Similarity	NPD4700	Approved
0.71	Intermediate Similarity	NPD3618	Phase 1
0.71	Intermediate Similarity	NPD5279	Phase 3
0.7097	Intermediate Similarity	NPD4058	Approved
0.7094	Intermediate Similarity	NPD7101	Approved
0.7094	Intermediate Similarity	NPD7100	Approved
0.7083	Intermediate Similarity	NPD7492	Approved
0.7075	Intermediate Similarity	NPD5173	Approved
0.7071	Intermediate Similarity	NPD4786	Approved
0.7071	Intermediate Similarity	NPD3668	Phase 3
0.7069	Intermediate Similarity	NPD6009	Approved
0.7064	Intermediate Similarity	NPD5174	Approved
0.7064	Intermediate Similarity	NPD5175	Approved
0.7059	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7736	Approved
0.7048	Intermediate Similarity	NPD4629	Approved
0.7048	Intermediate Similarity	NPD5210	Approved
0.7041	Intermediate Similarity	NPD4223	Phase 3
0.7041	Intermediate Similarity	NPD3667	Approved
0.7041	Intermediate Similarity	NPD4221	Approved
0.7037	Intermediate Similarity	NPD5223	Approved
0.7034	Intermediate Similarity	NPD6054	Approved
0.7027	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6616	Approved
0.7009	Intermediate Similarity	NPD6335	Approved
0.7	Intermediate Similarity	NPD1694	Approved
0.7	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD5141	Approved
0.6983	Remote Similarity	NPD6274	Approved
0.6983	Remote Similarity	NPD6868	Approved
0.6981	Remote Similarity	NPD7732	Phase 3
0.6981	Remote Similarity	NPD4697	Phase 3
0.6975	Remote Similarity	NPD5983	Phase 2
0.6967	Remote Similarity	NPD8293	Discontinued
0.6967	Remote Similarity	NPD7078	Approved
0.6957	Remote Similarity	NPD6858	Approved
0.6957	Remote Similarity	NPD7094	Approved
0.6931	Remote Similarity	NPD4694	Approved
0.6931	Remote Similarity	NPD4623	Approved
0.6931	Remote Similarity	NPD5280	Approved
0.6931	Remote Similarity	NPD4519	Discontinued
0.6923	Remote Similarity	NPD6317	Approved
0.6917	Remote Similarity	NPD6370	Approved
0.6915	Remote Similarity	NPD4687	Approved
0.6915	Remote Similarity	NPD5733	Approved
0.6909	Remote Similarity	NPD6052	Approved
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4197	Approved
0.6893	Remote Similarity	NPD6051	Approved
0.6891	Remote Similarity	NPD6059	Approved
0.6885	Remote Similarity	NPD6336	Discontinued
0.6875	Remote Similarity	NPD6614	Approved
0.6864	Remote Similarity	NPD6313	Approved
0.6864	Remote Similarity	NPD6314	Approved
0.6857	Remote Similarity	NPD5778	Approved
0.6857	Remote Similarity	NPD5779	Approved
0.6857	Remote Similarity	NPD4202	Approved
0.6852	Remote Similarity	NPD7638	Approved
0.6848	Remote Similarity	NPD4137	Phase 3
0.6842	Remote Similarity	NPD8039	Approved
0.6842	Remote Similarity	NPD4634	Approved
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6909	Approved
0.6833	Remote Similarity	NPD6908	Approved
0.6833	Remote Similarity	NPD6015	Approved
0.6833	Remote Similarity	NPD6016	Approved
0.6814	Remote Similarity	NPD4730	Approved
0.6814	Remote Similarity	NPD6686	Approved
0.6814	Remote Similarity	NPD4729	Approved
0.6789	Remote Similarity	NPD7640	Approved
0.6789	Remote Similarity	NPD7639	Approved
0.6786	Remote Similarity	NPD4768	Approved
0.6786	Remote Similarity	NPD4767	Approved
0.6777	Remote Similarity	NPD5988	Approved
0.6774	Remote Similarity	NPD4747	Approved
0.6774	Remote Similarity	NPD4691	Approved
0.6765	Remote Similarity	NPD4690	Approved
0.6765	Remote Similarity	NPD4689	Approved
0.6765	Remote Similarity	NPD5205	Approved
0.6765	Remote Similarity	NPD4138	Approved
0.6765	Remote Similarity	NPD4693	Phase 3
0.6765	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5690	Phase 2
0.6765	Remote Similarity	NPD4688	Approved
0.6762	Remote Similarity	NPD8034	Phase 2
0.6762	Remote Similarity	NPD8035	Phase 2
0.6757	Remote Similarity	NPD4754	Approved
0.6721	Remote Similarity	NPD8328	Phase 3
0.6702	Remote Similarity	NPD5276	Approved
0.67	Remote Similarity	NPD5209	Approved
0.67	Remote Similarity	NPD6435	Approved
0.6696	Remote Similarity	NPD5251	Approved
0.6696	Remote Similarity	NPD5248	Approved
0.6696	Remote Similarity	NPD5249	Phase 3
0.6696	Remote Similarity	NPD5247	Approved
0.6696	Remote Similarity	NPD5250	Approved
0.6694	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD5128	Approved
0.6638	Remote Similarity	NPD5216	Approved
0.6638	Remote Similarity	NPD5217	Approved
0.6638	Remote Similarity	NPD5215	Approved
0.6633	Remote Similarity	NPD3617	Approved
0.6613	Remote Similarity	NPD7507	Approved
0.6604	Remote Similarity	NPD7637	Suspended
0.6581	Remote Similarity	NPD6053	Discontinued
0.6574	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4195	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