NPASS Compound

Structure

CID71460 OpenBabel06191715412D 28 31 0 0 1 0 0 0 0 0999 V2000 -3.9926 6.3752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5325 5.6891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8042 3.7080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5322 2.4699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7403 3.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1684 4.6985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3441 3.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8434 -1.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6874 -0.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2183 1.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2180 0.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8431 0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6882 1.9476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 -1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5645 5.5876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3761 2.9204 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6867 -0.9738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3758 1.9471 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5316 0.4864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8440 0.4869 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 -2.5319 1.4602 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5529 -1.4736 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 19 3 1 1 0 0 0 19 23 1 0 0 0 0 20 26 1 6 0 0 0 21 28 1 6 0 0 0 22 10 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 27 1 6 0 0 0 24 27 1 6 0 0 0 25 26 1 6 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.37
Volume:	450.112
LogP:	8.262
LogD:	7.003
LogS:	-6.894
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	4.148
Fsp3:	1.0
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:	-4.701
MDCK Permeability:	1.7156224203063175e-05
Pgp-inhibitor:	0.928
Pgp-substrate:	0.063
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.699

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	94.0087661743164%
Volume Distribution (VD):	1.413
Pgp-substrate:	1.3071606159210205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.158
CYP1A2-substrate:	0.228
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.304
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	9.486
Half-life (T1/2):	0.072

ADMET: Toxicity

hERG Blockers:	0.98
Human Hepatotoxicity (H-HT):	0.185
Drug-inuced Liver Injury (DILI):	0.694
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.979
Carcinogencity:	0.099
Eye Corrosion:	0.997
Eye Irritation:	0.903
Respiratory Toxicity:	0.588

Download Data

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

Natural Product: NPC71460

Natural Product ID:	NPC71460
*Common Name:**	(3S,5S,10S,13R,17R)-17-((R)-1,5-Dimethyl-Hexyl)-10,13-Dimethyl-Hexadecahydro-Cyclopenta[A]Phenanthren-3-Ol
IUPAC Name:	(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	QYIXCDOBOSTCEI-QCYZZNICSA-N
Standard InCHI:	InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
SMILES:	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1289436
PubChem CID:	6665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	Flowers	Tantempango, Hidalgo, Mexico	2019-May	DOI[10.1007/s11130-020-00822-2]
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1453183]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16297615]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[18449498]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18543151]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24358188]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24767839]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623025]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778246]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2837	Aloe spicata	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2997	Aloe africana	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5679	Topsentia roquensis	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9839	Polanisia dodecandra	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27241	Prunus tomentosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6821	Tricholoma muscarium	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11588	Astragalus sevangensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4070	Eupatorium sternbergianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10954	Topsentia genitrix	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14763	Aloe ferox	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9636	Micromonospora coerulea	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1260	Chlorosplenium aeruginosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12496	Elsholtzia blanda	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2997	Aloe africana	Species	Xanthorrhoeaceae	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
NPO18674	NPC71460	Other (raw)	Seed	0.1	0	0.2	mg/100g	Database [DUKE]

☑ 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	3
Others	4

Activity Type	# Activity
Individual Protein	2
Organism	3
Others	1
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2215	Individual Protein	DNA polymerase alpha subunit	Homo sapiens	IC50	>	500000.0	nM	PMID[565806]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	>	500000.0	nM	PMID[565806]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	IC50	>	500000.0	nM	PMID[565806]
NPT20	Organism	Candida albicans	Candida albicans	GI	<	50.0	%	PMID[565808]
NPT554	Organism	Candida glabrata	Candida glabrata	GI	<	50.0	%	PMID[565808]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	GI	<	50.0	%	PMID[565808]
NPT35	Others	n.a.		Solubility	=	0.009	ug.mL-1	PMID[565809]

☑ 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 NPC71460 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	370
0.1-0.2	5106
0.2-0.3	18145
0.3-0.4	7880
0.4-0.5	4813
0.5-0.6	4053
0.6-0.7	1654
0.7-0.8	475
0.8-0.85	133
0.85-0.9	49
0.9-0.95	13
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC148174
1.0	High Similarity	NPC218585
0.9828	High Similarity	NPC114891
0.9661	High Similarity	NPC69149
0.95	High Similarity	NPC473276
0.95	High Similarity	NPC474380
0.95	High Similarity	NPC41577
0.9344	High Similarity	NPC142712
0.9333	High Similarity	NPC167995
0.9333	High Similarity	NPC159654
0.9333	High Similarity	NPC118937
0.9333	High Similarity	NPC281540
0.9194	High Similarity	NPC475884
0.9194	High Similarity	NPC473230
0.9194	High Similarity	NPC48079
0.9138	High Similarity	NPC476735
0.9048	High Similarity	NPC472741
0.9032	High Similarity	NPC44122
0.8906	High Similarity	NPC129829
0.8906	High Similarity	NPC241085
0.8906	High Similarity	NPC470830
0.8906	High Similarity	NPC66407
0.8906	High Similarity	NPC107919
0.8906	High Similarity	NPC477820
0.8906	High Similarity	NPC299948
0.8906	High Similarity	NPC254037
0.8769	High Similarity	NPC192192
0.8769	High Similarity	NPC251201
0.8769	High Similarity	NPC232925
0.8769	High Similarity	NPC282454
0.8769	High Similarity	NPC63588
0.8769	High Similarity	NPC231945
0.8636	High Similarity	NPC157422
0.8636	High Similarity	NPC109457
0.8636	High Similarity	NPC127094
0.8636	High Similarity	NPC58057
0.8636	High Similarity	NPC478103
0.8636	High Similarity	NPC320549
0.8636	High Similarity	NPC100586
0.8636	High Similarity	NPC111234
0.8636	High Similarity	NPC156277
0.8636	High Similarity	NPC1340
0.8636	High Similarity	NPC187471
0.8636	High Similarity	NPC470071
0.8636	High Similarity	NPC473279
0.8636	High Similarity	NPC195530
0.8636	High Similarity	NPC151018
0.8636	High Similarity	NPC252182
0.8594	High Similarity	NPC63190
0.8571	High Similarity	NPC243469
0.8571	High Similarity	NPC190827
0.8571	High Similarity	NPC475943
0.8548	High Similarity	NPC292419
0.8548	High Similarity	NPC290791
0.8507	High Similarity	NPC153719
0.8507	High Similarity	NPC195489
0.8507	High Similarity	NPC472341
0.8507	High Similarity	NPC470610
0.8507	High Similarity	NPC232112
0.8507	High Similarity	NPC473238
0.85	High Similarity	NPC162685
0.8485	Intermediate Similarity	NPC45296
0.8382	Intermediate Similarity	NPC478130
0.8382	Intermediate Similarity	NPC196358
0.8382	Intermediate Similarity	NPC62657
0.8382	Intermediate Similarity	NPC145552
0.8382	Intermediate Similarity	NPC254509
0.8382	Intermediate Similarity	NPC228994
0.8382	Intermediate Similarity	NPC48795
0.8382	Intermediate Similarity	NPC280026
0.8382	Intermediate Similarity	NPC192638
0.8382	Intermediate Similarity	NPC5046
0.8382	Intermediate Similarity	NPC192501
0.8382	Intermediate Similarity	NPC477508
0.8382	Intermediate Similarity	NPC10476
0.8382	Intermediate Similarity	NPC25511
0.8382	Intermediate Similarity	NPC49168
0.8382	Intermediate Similarity	NPC304499
0.8382	Intermediate Similarity	NPC167702
0.8382	Intermediate Similarity	NPC254340
0.8361	Intermediate Similarity	NPC95958
0.8358	Intermediate Similarity	NPC131506
0.8358	Intermediate Similarity	NPC157777
0.8333	Intermediate Similarity	NPC99264
0.8333	Intermediate Similarity	NPC135438
0.8333	Intermediate Similarity	NPC327728
0.8333	Intermediate Similarity	NPC213178
0.8333	Intermediate Similarity	NPC131892
0.8333	Intermediate Similarity	NPC6120
0.8281	Intermediate Similarity	NPC472946
0.8281	Intermediate Similarity	NPC477603
0.8281	Intermediate Similarity	NPC260116
0.8281	Intermediate Similarity	NPC80463
0.8261	Intermediate Similarity	NPC97534
0.8261	Intermediate Similarity	NPC174964
0.8261	Intermediate Similarity	NPC230704
0.8261	Intermediate Similarity	NPC240235
0.8261	Intermediate Similarity	NPC195155
0.8261	Intermediate Similarity	NPC212879
0.8261	Intermediate Similarity	NPC70982
0.8261	Intermediate Similarity	NPC178383
0.8261	Intermediate Similarity	NPC243027
0.8261	Intermediate Similarity	NPC212733
0.8261	Intermediate Similarity	NPC3403
0.8261	Intermediate Similarity	NPC231680
0.8261	Intermediate Similarity	NPC231256
0.8261	Intermediate Similarity	NPC158208
0.8261	Intermediate Similarity	NPC270306
0.8261	Intermediate Similarity	NPC317242
0.8261	Intermediate Similarity	NPC273366
0.8261	Intermediate Similarity	NPC200243
0.8261	Intermediate Similarity	NPC91387
0.8261	Intermediate Similarity	NPC103822
0.8261	Intermediate Similarity	NPC196136
0.8261	Intermediate Similarity	NPC185536
0.8261	Intermediate Similarity	NPC104387
0.8254	Intermediate Similarity	NPC236099
0.8254	Intermediate Similarity	NPC209686
0.8254	Intermediate Similarity	NPC249078
0.8182	Intermediate Similarity	NPC474756
0.8143	Intermediate Similarity	NPC163597
0.8143	Intermediate Similarity	NPC470145
0.8143	Intermediate Similarity	NPC86305
0.8143	Intermediate Similarity	NPC4209
0.8143	Intermediate Similarity	NPC278091
0.8143	Intermediate Similarity	NPC78067
0.8143	Intermediate Similarity	NPC5767
0.8143	Intermediate Similarity	NPC237460
0.8143	Intermediate Similarity	NPC477602
0.8143	Intermediate Similarity	NPC472486
0.8143	Intermediate Similarity	NPC473916
0.8143	Intermediate Similarity	NPC477601
0.8143	Intermediate Similarity	NPC14112
0.8143	Intermediate Similarity	NPC91573
0.8143	Intermediate Similarity	NPC93662
0.8143	Intermediate Similarity	NPC472487
0.8143	Intermediate Similarity	NPC475742
0.8116	Intermediate Similarity	NPC472503
0.8116	Intermediate Similarity	NPC308440
0.8095	Intermediate Similarity	NPC95804
0.8095	Intermediate Similarity	NPC185547
0.8088	Intermediate Similarity	NPC89310
0.8088	Intermediate Similarity	NPC8004
0.8088	Intermediate Similarity	NPC127283
0.8033	Intermediate Similarity	NPC236588
0.803	Intermediate Similarity	NPC475172
0.803	Intermediate Similarity	NPC204233
0.8028	Intermediate Similarity	NPC105208
0.8028	Intermediate Similarity	NPC23884
0.8028	Intermediate Similarity	NPC476233
0.8028	Intermediate Similarity	NPC11907
0.8028	Intermediate Similarity	NPC221420
0.8028	Intermediate Similarity	NPC119355
0.8028	Intermediate Similarity	NPC133596
0.8028	Intermediate Similarity	NPC302578
0.8028	Intermediate Similarity	NPC64081
0.8028	Intermediate Similarity	NPC212241
0.8028	Intermediate Similarity	NPC257191
0.8028	Intermediate Similarity	NPC128951
0.8028	Intermediate Similarity	NPC202540
0.8028	Intermediate Similarity	NPC298168
0.8028	Intermediate Similarity	NPC192046
0.8028	Intermediate Similarity	NPC207010
0.8028	Intermediate Similarity	NPC477227
0.8028	Intermediate Similarity	NPC248830
0.8028	Intermediate Similarity	NPC475031
0.8028	Intermediate Similarity	NPC185915
0.8028	Intermediate Similarity	NPC143133
0.8028	Intermediate Similarity	NPC331618
0.8028	Intermediate Similarity	NPC317913
0.8028	Intermediate Similarity	NPC474574
0.8	Intermediate Similarity	NPC257347
0.8	Intermediate Similarity	NPC125767
0.8	Intermediate Similarity	NPC476737
0.8	Intermediate Similarity	NPC21220
0.8	Intermediate Similarity	NPC141071
0.8	Intermediate Similarity	NPC27243
0.8	Intermediate Similarity	NPC471723
0.7971	Intermediate Similarity	NPC310766
0.7971	Intermediate Similarity	NPC201373
0.7917	Intermediate Similarity	NPC185465
0.7917	Intermediate Similarity	NPC80089
0.7917	Intermediate Similarity	NPC34046
0.7917	Intermediate Similarity	NPC102708
0.7917	Intermediate Similarity	NPC65897
0.7917	Intermediate Similarity	NPC285761
0.7917	Intermediate Similarity	NPC167037
0.7917	Intermediate Similarity	NPC147993
0.7917	Intermediate Similarity	NPC301707
0.7917	Intermediate Similarity	NPC302041
0.7917	Intermediate Similarity	NPC31828
0.7917	Intermediate Similarity	NPC6978
0.7917	Intermediate Similarity	NPC477817
0.7917	Intermediate Similarity	NPC472342
0.7917	Intermediate Similarity	NPC18857
0.7917	Intermediate Similarity	NPC471769
0.7917	Intermediate Similarity	NPC42853
0.7917	Intermediate Similarity	NPC67657
0.7917	Intermediate Similarity	NPC171426
0.7917	Intermediate Similarity	NPC138621

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 NPC71460 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	4541
0.2-0.3	3071
0.3-0.4	657
0.4-0.5	205
0.5-0.6	192
0.6-0.7	66
0.7-0.8	15
0.8-0.85	14
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD4267	Clinical (unspecified phase)
0.8769	High Similarity	NPD4787	Phase 1
0.8636	High Similarity	NPD4809	Clinical (unspecified phase)
0.8636	High Similarity	NPD4808	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD6117	Approved
0.8028	Intermediate Similarity	NPD6116	Phase 1
0.7941	Intermediate Similarity	NPD4789	Approved
0.7941	Intermediate Similarity	NPD4245	Approved
0.7941	Intermediate Similarity	NPD4244	Approved
0.7917	Intermediate Similarity	NPD6697	Approved
0.7917	Intermediate Similarity	NPD6118	Approved
0.7917	Intermediate Similarity	NPD6115	Approved
0.7917	Intermediate Similarity	NPD6114	Approved
0.791	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD5360	Phase 3
0.7794	Intermediate Similarity	NPD3698	Phase 2
0.7746	Intermediate Similarity	NPD6942	Approved
0.7746	Intermediate Similarity	NPD7339	Approved
0.7746	Intermediate Similarity	NPD3703	Phase 2
0.7727	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6928	Phase 2
0.7703	Intermediate Similarity	NPD7525	Registered
0.7432	Intermediate Similarity	NPD3671	Phase 1
0.7391	Intermediate Similarity	NPD6705	Phase 1
0.7324	Intermediate Similarity	NPD4758	Discontinued
0.7241	Intermediate Similarity	NPD385	Approved
0.7241	Intermediate Similarity	NPD384	Approved
0.7215	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4224	Phase 2
0.7083	Intermediate Similarity	NPD6081	Approved
0.7013	Intermediate Similarity	NPD4748	Discontinued
0.6974	Remote Similarity	NPD5364	Discontinued
0.6892	Remote Similarity	NPD6924	Approved
0.6892	Remote Similarity	NPD6926	Approved
0.6883	Remote Similarity	NPD7645	Phase 2
0.6875	Remote Similarity	NPD4786	Approved
0.6849	Remote Similarity	NPD7151	Approved
0.6849	Remote Similarity	NPD7150	Approved
0.6849	Remote Similarity	NPD7152	Approved
0.6849	Remote Similarity	NPD4243	Approved
0.6849	Remote Similarity	NPD5777	Approved
0.6806	Remote Similarity	NPD6923	Approved
0.6806	Remote Similarity	NPD6922	Approved
0.68	Remote Similarity	NPD3702	Approved
0.6786	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6700	Approved
0.675	Remote Similarity	NPD4788	Approved
0.6712	Remote Similarity	NPD7144	Approved
0.6712	Remote Similarity	NPD7143	Approved
0.6711	Remote Similarity	NPD6933	Approved
0.6706	Remote Similarity	NPD6702	Approved
0.6706	Remote Similarity	NPD6703	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6628	Remote Similarity	NPD8171	Discontinued
0.6625	Remote Similarity	NPD3667	Approved
0.6512	Remote Similarity	NPD8035	Phase 2
0.6512	Remote Similarity	NPD6079	Approved
0.6512	Remote Similarity	NPD8034	Phase 2
0.6506	Remote Similarity	NPD3618	Phase 1
0.6456	Remote Similarity	NPD6929	Approved
0.6429	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7509	Discontinued
0.6375	Remote Similarity	NPD6930	Phase 2
0.6375	Remote Similarity	NPD6931	Approved
0.6364	Remote Similarity	NPD5275	Approved
0.6364	Remote Similarity	NPD4190	Phase 3
0.6333	Remote Similarity	NPD7920	Phase 3
0.6333	Remote Similarity	NPD7919	Phase 3
0.631	Remote Similarity	NPD8308	Discontinued
0.6292	Remote Similarity	NPD7991	Discontinued
0.6265	Remote Similarity	NPD3665	Phase 1
0.6265	Remote Similarity	NPD3133	Approved
0.6265	Remote Similarity	NPD3666	Approved
0.6264	Remote Similarity	NPD8088	Phase 1
0.625	Remote Similarity	NPD4202	Approved
0.623	Remote Similarity	NPD388	Approved
0.623	Remote Similarity	NPD386	Approved
0.6203	Remote Similarity	NPD5776	Phase 2
0.6203	Remote Similarity	NPD6932	Approved
0.6203	Remote Similarity	NPD6925	Approved
0.6196	Remote Similarity	NPD8418	Phase 2
0.6145	Remote Similarity	NPD6695	Phase 3
0.6125	Remote Similarity	NPD7145	Approved
0.6111	Remote Similarity	NPD371	Approved
0.6087	Remote Similarity	NPD7638	Approved
0.6071	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD6399	Phase 3
0.6049	Remote Similarity	NPD4195	Approved
0.6049	Remote Similarity	NPD6683	Phase 2
0.6044	Remote Similarity	NPD5221	Approved
0.6044	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4697	Phase 3
0.6044	Remote Similarity	NPD5222	Approved
0.6022	Remote Similarity	NPD7639	Approved
0.6022	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD3198	Approved
0.5978	Remote Similarity	NPD4755	Approved
0.5978	Remote Similarity	NPD5173	Approved
0.5976	Remote Similarity	NPD7514	Phase 3
0.5955	Remote Similarity	NPD7515	Phase 2
0.5938	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.593	Remote Similarity	NPD5279	Phase 3
0.5926	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3617	Approved
0.5909	Remote Similarity	NPD4753	Phase 2
0.5904	Remote Similarity	NPD6902	Approved
0.5895	Remote Similarity	NPD7632	Discontinued
0.5882	Remote Similarity	NPD3668	Phase 3
0.5876	Remote Similarity	NPD6920	Discontinued
0.5862	Remote Similarity	NPD7524	Approved
0.5862	Remote Similarity	NPD7750	Discontinued
0.5851	Remote Similarity	NPD5285	Approved
0.5851	Remote Similarity	NPD5286	Approved
0.5851	Remote Similarity	NPD4696	Approved
0.5851	Remote Similarity	NPD4700	Approved
0.5833	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD4223	Phase 3
0.5814	Remote Similarity	NPD5329	Approved
0.5797	Remote Similarity	NPD586	Phase 1
0.5789	Remote Similarity	NPD5223	Approved
0.5783	Remote Similarity	NPD7332	Phase 2
0.5758	Remote Similarity	NPD6415	Discontinued
0.575	Remote Similarity	NPD8264	Approved
0.5745	Remote Similarity	NPD5290	Discontinued
0.5729	Remote Similarity	NPD5226	Approved
0.5729	Remote Similarity	NPD5225	Approved
0.5729	Remote Similarity	NPD5211	Phase 2
0.5729	Remote Similarity	NPD5224	Approved
0.5729	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD4139	Approved
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6898	Phase 1
0.5714	Remote Similarity	NPD4692	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5698	Remote Similarity	NPD4197	Approved
0.567	Remote Similarity	NPD5175	Approved
0.567	Remote Similarity	NPD4754	Approved
0.567	Remote Similarity	NPD5174	Approved
0.5657	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD7748	Approved
0.5645	Remote Similarity	NPD367	Approved
0.5638	Remote Similarity	NPD6083	Phase 2
0.5638	Remote Similarity	NPD6084	Phase 2
0.5625	Remote Similarity	NPD4159	Approved
0.5625	Remote Similarity	NPD1811	Approved
0.5625	Remote Similarity	NPD1810	Approved
0.5618	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5141	Approved
0.5604	Remote Similarity	NPD7087	Discontinued
0.56	Remote Similarity	NPD6899	Approved
0.56	Remote Similarity	NPD7320	Approved
0.56	Remote Similarity	NPD6881	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