NPASS Compound

Structure

CID129913 OpenBabel06191715492D 25 28 0 0 1 0 0 0 0 0999 V2000 2.5207 -0.4485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6812 -2.9093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8409 -2.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6789 -0.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6792 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2002 -1.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3605 -0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3610 -2.9089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6804 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0806 1.7540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5213 -2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2005 -2.4235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -1.4544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9695 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8403 0.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6807 -0.9691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8409 1.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5210 -1.4539 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 0.2816 2.7021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0714 -2.9259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5615 2.1020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 10 19 1 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 12 20 1 0 0 0 0 13 23 2 0 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 21 1 6 0 0 0 16 18 1 0 0 0 0 16 21 1 6 0 0 0 17 20 1 6 0 0 0 18 24 2 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 20 1 1 6 0 0 0 21 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.18
Volume:	359.525
LogP:	1.486
LogD:	0.137
LogS:	-2.413
# Rotatable Bonds:	2
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.838
Synthetic Accessibility Score:	4.643
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	2.89535219053505e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.111
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.471
Plasma Protein Binding (PPB):	51.774635314941406%
Volume Distribution (VD):	0.415
Pgp-substrate:	47.96772766113281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.655
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.78

ADMET: Excretion

Clearance (CL):	6.992
Half-life (T1/2):	0.932

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.315
AMES Toxicity:	0.197
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.909
Carcinogencity:	0.781
Eye Corrosion:	0.895
Eye Irritation:	0.412
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC129913

Natural Product ID:	NPC129913
*Common Name:**	21-Hydroxypregna-4,6-Diene-3,12,20-Trione
IUPAC Name:	(8R,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-2,8,9,11,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,12-dione
Synonyms:
Standard InCHIKey:	BORCINXYCLOGNE-QPQISGKWSA-N
Standard InCHI:	InChI=1S/C21H26O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(24)11-22)21(15,2)19(25)10-17(14)20/h3-4,9,14-17,22H,5-8,10-11H2,1-2H3/t14-,15-,16+,17-,20-,21-/m0/s1
SMILES:	C[C@]12CCC(=O)C=C1C=C[C@H]1[C@@H]3CC[C@H](C(=O)CO)[C@@]3(C)C(=O)C[C@H]21
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL216149
PubChem CID:	16104852
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003095] 21-hydroxysteroids

*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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277760]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14048	Cryptotaenia japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12987	Rhododendron farrerae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18054	Curvularia coicis	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24652	Toxicodendron succedaneum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	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	3
Others	3

Activity Type	# Activity
Cell Line	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	87.7	ug.mL-1	PMID[476984]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	94.9	ug.mL-1	PMID[476984]
NPT2	Others	Unspecified		Activity	=	110.0	%	PMID[476984]
NPT2	Others	Unspecified		Activity	=	105.0	%	PMID[476984]
NPT2	Others	Unspecified		Activity	=	140.0	%	PMID[476984]
NPT27	Others	Unspecified		IC50	=	48.1	ug.mL-1	PMID[476984]

☑ 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 NPC129913 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	167
0.1-0.2	930
0.2-0.3	4733
0.3-0.4	13867
0.4-0.5	9790
0.5-0.6	7479
0.6-0.7	4271
0.7-0.8	1259
0.8-0.85	178
0.85-0.9	20
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9205	High Similarity	NPC19114
0.9186	High Similarity	NPC136548
0.9059	High Similarity	NPC237712
0.8851	High Similarity	NPC327115
0.8837	High Similarity	NPC473246
0.8778	High Similarity	NPC168027
0.8778	High Similarity	NPC185936
0.8764	High Similarity	NPC326627
0.8764	High Similarity	NPC310010
0.8736	High Similarity	NPC469948
0.8636	High Similarity	NPC475022
0.8636	High Similarity	NPC118648
0.8636	High Similarity	NPC222613
0.8621	High Similarity	NPC214043
0.8621	High Similarity	NPC85774
0.8605	High Similarity	NPC103486
0.8602	High Similarity	NPC192428
0.8556	High Similarity	NPC275740
0.8556	High Similarity	NPC86319
0.8556	High Similarity	NPC477943
0.8539	High Similarity	NPC93778
0.8539	High Similarity	NPC58063
0.8495	Intermediate Similarity	NPC280725
0.8488	Intermediate Similarity	NPC121984
0.8488	Intermediate Similarity	NPC225515
0.8478	Intermediate Similarity	NPC474807
0.8478	Intermediate Similarity	NPC233118
0.8478	Intermediate Similarity	NPC250575
0.8478	Intermediate Similarity	NPC134826
0.8478	Intermediate Similarity	NPC472930
0.8471	Intermediate Similarity	NPC472490
0.8444	Intermediate Similarity	NPC131470
0.8444	Intermediate Similarity	NPC143767
0.8444	Intermediate Similarity	NPC471722
0.8444	Intermediate Similarity	NPC44181
0.8444	Intermediate Similarity	NPC328539
0.8427	Intermediate Similarity	NPC72133
0.8427	Intermediate Similarity	NPC51014
0.8427	Intermediate Similarity	NPC31564
0.8427	Intermediate Similarity	NPC89077
0.8427	Intermediate Similarity	NPC474732
0.8427	Intermediate Similarity	NPC474778
0.8427	Intermediate Similarity	NPC145879
0.8427	Intermediate Similarity	NPC474733
0.8427	Intermediate Similarity	NPC20688
0.8421	Intermediate Similarity	NPC147954
0.8409	Intermediate Similarity	NPC321187
0.8409	Intermediate Similarity	NPC161423
0.8409	Intermediate Similarity	NPC227064
0.8409	Intermediate Similarity	NPC329043
0.8409	Intermediate Similarity	NPC144258
0.8409	Intermediate Similarity	NPC58841
0.8404	Intermediate Similarity	NPC305483
0.8404	Intermediate Similarity	NPC249954
0.8404	Intermediate Similarity	NPC96859
0.8404	Intermediate Similarity	NPC328162
0.8387	Intermediate Similarity	NPC473172
0.8387	Intermediate Similarity	NPC196485
0.8387	Intermediate Similarity	NPC245972
0.8372	Intermediate Similarity	NPC472478
0.837	Intermediate Similarity	NPC204341
0.8352	Intermediate Similarity	NPC474245
0.8352	Intermediate Similarity	NPC186688
0.8352	Intermediate Similarity	NPC31985
0.8352	Intermediate Similarity	NPC123912
0.8352	Intermediate Similarity	NPC1015
0.8333	Intermediate Similarity	NPC287079
0.8333	Intermediate Similarity	NPC141292
0.8333	Intermediate Similarity	NPC475740
0.8333	Intermediate Similarity	NPC144956
0.8333	Intermediate Similarity	NPC474720
0.8316	Intermediate Similarity	NPC18509
0.8316	Intermediate Similarity	NPC473161
0.8316	Intermediate Similarity	NPC43747
0.8315	Intermediate Similarity	NPC474083
0.8298	Intermediate Similarity	NPC127063
0.8298	Intermediate Similarity	NPC472932
0.8298	Intermediate Similarity	NPC259286
0.8295	Intermediate Similarity	NPC69279
0.8295	Intermediate Similarity	NPC83569
0.828	Intermediate Similarity	NPC472942
0.828	Intermediate Similarity	NPC66429
0.828	Intermediate Similarity	NPC69454
0.828	Intermediate Similarity	NPC152897
0.8276	Intermediate Similarity	NPC116797
0.8276	Intermediate Similarity	NPC55869
0.8265	Intermediate Similarity	NPC111323
0.8261	Intermediate Similarity	NPC191684
0.8261	Intermediate Similarity	NPC69622
0.8261	Intermediate Similarity	NPC183283
0.8256	Intermediate Similarity	NPC474113
0.8242	Intermediate Similarity	NPC292491
0.8242	Intermediate Similarity	NPC310752
0.8229	Intermediate Similarity	NPC471717
0.8229	Intermediate Similarity	NPC235464
0.8229	Intermediate Similarity	NPC166745
0.8222	Intermediate Similarity	NPC473168
0.8222	Intermediate Similarity	NPC94666
0.8211	Intermediate Similarity	NPC473164
0.8202	Intermediate Similarity	NPC82902
0.8202	Intermediate Similarity	NPC221758
0.8202	Intermediate Similarity	NPC59453
0.8191	Intermediate Similarity	NPC166906
0.8191	Intermediate Similarity	NPC473162
0.8191	Intermediate Similarity	NPC8993
0.8182	Intermediate Similarity	NPC193347
0.8182	Intermediate Similarity	NPC151519
0.8172	Intermediate Similarity	NPC473998
0.8172	Intermediate Similarity	NPC475806
0.8172	Intermediate Similarity	NPC63748
0.8172	Intermediate Similarity	NPC272746
0.8163	Intermediate Similarity	NPC87351
0.8161	Intermediate Similarity	NPC108955
0.8161	Intermediate Similarity	NPC2482
0.8152	Intermediate Similarity	NPC76879
0.8152	Intermediate Similarity	NPC84271
0.8152	Intermediate Similarity	NPC309603
0.8152	Intermediate Similarity	NPC102414
0.8152	Intermediate Similarity	NPC26959
0.8152	Intermediate Similarity	NPC77168
0.8152	Intermediate Similarity	NPC473999
0.8152	Intermediate Similarity	NPC268406
0.8144	Intermediate Similarity	NPC51370
0.814	Intermediate Similarity	NPC189485
0.814	Intermediate Similarity	NPC82635
0.8132	Intermediate Similarity	NPC96496
0.8132	Intermediate Similarity	NPC99909
0.8132	Intermediate Similarity	NPC90652
0.8132	Intermediate Similarity	NPC317590
0.8111	Intermediate Similarity	NPC8518
0.8111	Intermediate Similarity	NPC263997
0.8111	Intermediate Similarity	NPC474218
0.8111	Intermediate Similarity	NPC32037
0.8111	Intermediate Similarity	NPC473038
0.8111	Intermediate Similarity	NPC132228
0.8111	Intermediate Similarity	NPC470574
0.8111	Intermediate Similarity	NPC29447
0.8111	Intermediate Similarity	NPC471224
0.8105	Intermediate Similarity	NPC174948
0.8105	Intermediate Similarity	NPC171395
0.8105	Intermediate Similarity	NPC317586
0.8105	Intermediate Similarity	NPC263347
0.8105	Intermediate Similarity	NPC318282
0.8105	Intermediate Similarity	NPC173875
0.8105	Intermediate Similarity	NPC470016
0.8105	Intermediate Similarity	NPC469995
0.809	Intermediate Similarity	NPC278648
0.809	Intermediate Similarity	NPC476082
0.809	Intermediate Similarity	NPC470015
0.809	Intermediate Similarity	NPC168188
0.8085	Intermediate Similarity	NPC474736
0.8085	Intermediate Similarity	NPC211230
0.8085	Intermediate Similarity	NPC475255
0.8085	Intermediate Similarity	NPC25750
0.8085	Intermediate Similarity	NPC12722
0.8081	Intermediate Similarity	NPC311612
0.8068	Intermediate Similarity	NPC477372
0.8068	Intermediate Similarity	NPC4166
0.8068	Intermediate Similarity	NPC201912
0.8068	Intermediate Similarity	NPC38350
0.8065	Intermediate Similarity	NPC48010
0.8065	Intermediate Similarity	NPC320026
0.8065	Intermediate Similarity	NPC46281
0.8061	Intermediate Similarity	NPC302537
0.8061	Intermediate Similarity	NPC163372
0.8046	Intermediate Similarity	NPC27817
0.8043	Intermediate Similarity	NPC470417
0.8043	Intermediate Similarity	NPC471724
0.8041	Intermediate Similarity	NPC114274
0.8041	Intermediate Similarity	NPC197386
0.8041	Intermediate Similarity	NPC191565
0.8041	Intermediate Similarity	NPC103051
0.8022	Intermediate Similarity	NPC469994
0.8022	Intermediate Similarity	NPC94755
0.8022	Intermediate Similarity	NPC6247
0.8021	Intermediate Similarity	NPC49371
0.8021	Intermediate Similarity	NPC456
0.8021	Intermediate Similarity	NPC328371
0.8021	Intermediate Similarity	NPC155676
0.8021	Intermediate Similarity	NPC472941
0.8	Intermediate Similarity	NPC299100
0.8	Intermediate Similarity	NPC56525
0.8	Intermediate Similarity	NPC49670
0.8	Intermediate Similarity	NPC235889
0.8	Intermediate Similarity	NPC111015
0.8	Intermediate Similarity	NPC33913
0.8	Intermediate Similarity	NPC469406
0.8	Intermediate Similarity	NPC472265
0.8	Intermediate Similarity	NPC474882
0.8	Intermediate Similarity	NPC474690
0.8	Intermediate Similarity	NPC474328
0.798	Intermediate Similarity	NPC204450
0.798	Intermediate Similarity	NPC195290
0.798	Intermediate Similarity	NPC119601
0.798	Intermediate Similarity	NPC308726
0.7979	Intermediate Similarity	NPC233116
0.7979	Intermediate Similarity	NPC297265
0.7979	Intermediate Similarity	NPC99380
0.7978	Intermediate Similarity	NPC133391
0.7978	Intermediate Similarity	NPC311092

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 NPC129913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1196
0.2-0.3	3914
0.3-0.4	2714
0.4-0.5	686
0.5-0.6	194
0.6-0.7	136
0.7-0.8	120
0.8-0.85	40
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9294	High Similarity	NPD5279	Phase 3
0.8851	High Similarity	NPD4694	Approved
0.8851	High Similarity	NPD5280	Approved
0.8764	High Similarity	NPD4753	Phase 2
0.8636	High Similarity	NPD5690	Phase 2
0.8602	High Similarity	NPD5222	Approved
0.8602	High Similarity	NPD4697	Phase 3
0.8602	High Similarity	NPD5221	Approved
0.8602	High Similarity	NPD5220	Clinical (unspecified phase)
0.8511	High Similarity	NPD5173	Approved
0.8495	Intermediate Similarity	NPD4629	Approved
0.8495	Intermediate Similarity	NPD5210	Approved
0.8409	Intermediate Similarity	NPD3666	Approved
0.8409	Intermediate Similarity	NPD4197	Approved
0.8409	Intermediate Similarity	NPD3665	Phase 1
0.8409	Intermediate Similarity	NPD3133	Approved
0.837	Intermediate Similarity	NPD5281	Approved
0.837	Intermediate Similarity	NPD6079	Approved
0.837	Intermediate Similarity	NPD5284	Approved
0.8352	Intermediate Similarity	NPD5328	Approved
0.8333	Intermediate Similarity	NPD5285	Approved
0.8333	Intermediate Similarity	NPD5286	Approved
0.8333	Intermediate Similarity	NPD4696	Approved
0.8316	Intermediate Similarity	NPD4755	Approved
0.8315	Intermediate Similarity	NPD5329	Approved
0.8298	Intermediate Similarity	NPD5695	Phase 3
0.8247	Intermediate Similarity	NPD5223	Approved
0.8222	Intermediate Similarity	NPD3618	Phase 1
0.8202	Intermediate Similarity	NPD4786	Approved
0.8182	Intermediate Similarity	NPD4221	Approved
0.8182	Intermediate Similarity	NPD4223	Phase 3
0.8182	Intermediate Similarity	NPD3667	Approved
0.8172	Intermediate Similarity	NPD5694	Approved
0.8163	Intermediate Similarity	NPD5225	Approved
0.8163	Intermediate Similarity	NPD4633	Approved
0.8163	Intermediate Similarity	NPD5211	Phase 2
0.8163	Intermediate Similarity	NPD5224	Approved
0.8163	Intermediate Similarity	NPD5226	Approved
0.8144	Intermediate Similarity	NPD4700	Approved
0.814	Intermediate Similarity	NPD3617	Approved
0.8125	Intermediate Similarity	NPD6083	Phase 2
0.8125	Intermediate Similarity	NPD6084	Phase 2
0.8095	Intermediate Similarity	NPD4687	Approved
0.8085	Intermediate Similarity	NPD5133	Approved
0.8081	Intermediate Similarity	NPD5174	Approved
0.8081	Intermediate Similarity	NPD5175	Approved
0.8065	Intermediate Similarity	NPD5692	Phase 3
0.8043	Intermediate Similarity	NPD6672	Approved
0.8043	Intermediate Similarity	NPD5737	Approved
0.8	Intermediate Similarity	NPD5141	Approved
0.7979	Intermediate Similarity	NPD6050	Approved
0.7955	Intermediate Similarity	NPD4695	Discontinued
0.79	Intermediate Similarity	NPD4754	Approved
0.7895	Intermediate Similarity	NPD4202	Approved
0.7882	Intermediate Similarity	NPD5733	Approved
0.7872	Intermediate Similarity	NPD4096	Approved
0.7857	Intermediate Similarity	NPD5276	Approved
0.7857	Intermediate Similarity	NPD5696	Approved
0.7849	Intermediate Similarity	NPD4518	Approved
0.7843	Intermediate Similarity	NPD5697	Approved
0.7826	Intermediate Similarity	NPD5205	Approved
0.7826	Intermediate Similarity	NPD4689	Approved
0.7826	Intermediate Similarity	NPD4693	Phase 3
0.7826	Intermediate Similarity	NPD4690	Approved
0.7826	Intermediate Similarity	NPD4688	Approved
0.7826	Intermediate Similarity	NPD4138	Approved
0.7767	Intermediate Similarity	NPD6899	Approved
0.7767	Intermediate Similarity	NPD4729	Approved
0.7767	Intermediate Similarity	NPD4730	Approved
0.7767	Intermediate Similarity	NPD6011	Approved
0.7767	Intermediate Similarity	NPD5168	Approved
0.7767	Intermediate Similarity	NPD6881	Approved
0.7766	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD4768	Approved
0.7745	Intermediate Similarity	NPD6675	Approved
0.7745	Intermediate Similarity	NPD5739	Approved
0.7745	Intermediate Similarity	NPD7128	Approved
0.7745	Intermediate Similarity	NPD4767	Approved
0.7745	Intermediate Similarity	NPD6402	Approved
0.7714	Intermediate Similarity	NPD6649	Approved
0.7714	Intermediate Similarity	NPD6650	Approved
0.7708	Intermediate Similarity	NPD6399	Phase 3
0.7692	Intermediate Similarity	NPD6013	Approved
0.7692	Intermediate Similarity	NPD6014	Approved
0.7692	Intermediate Similarity	NPD6373	Approved
0.7692	Intermediate Similarity	NPD6012	Approved
0.7692	Intermediate Similarity	NPD6372	Approved
0.7684	Intermediate Similarity	NPD5207	Approved
0.7674	Intermediate Similarity	NPD4058	Approved
0.767	Intermediate Similarity	NPD5701	Approved
0.764	Intermediate Similarity	NPD4195	Approved
0.7634	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5247	Approved
0.7619	Intermediate Similarity	NPD5135	Approved
0.7619	Intermediate Similarity	NPD7290	Approved
0.7619	Intermediate Similarity	NPD5169	Approved
0.7619	Intermediate Similarity	NPD5248	Approved
0.7619	Intermediate Similarity	NPD5249	Phase 3
0.7619	Intermediate Similarity	NPD4634	Approved
0.7619	Intermediate Similarity	NPD5251	Approved
0.7619	Intermediate Similarity	NPD5250	Approved
0.7619	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6883	Approved
0.7619	Intermediate Similarity	NPD7102	Approved
0.7609	Intermediate Similarity	NPD3668	Phase 3
0.7596	Intermediate Similarity	NPD5128	Approved
0.7596	Intermediate Similarity	NPD7320	Approved
0.7579	Intermediate Similarity	NPD6673	Approved
0.7579	Intermediate Similarity	NPD6080	Approved
0.7579	Intermediate Similarity	NPD6904	Approved
0.7556	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5654	Approved
0.7547	Intermediate Similarity	NPD6617	Approved
0.7547	Intermediate Similarity	NPD5127	Approved
0.7547	Intermediate Similarity	NPD5216	Approved
0.7547	Intermediate Similarity	NPD6869	Approved
0.7547	Intermediate Similarity	NPD6847	Approved
0.7547	Intermediate Similarity	NPD8130	Phase 1
0.7547	Intermediate Similarity	NPD5217	Approved
0.7547	Intermediate Similarity	NPD5215	Approved
0.7529	Intermediate Similarity	NPD4747	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.7477	Intermediate Similarity	NPD6882	Approved
0.7477	Intermediate Similarity	NPD8297	Approved
0.7473	Intermediate Similarity	NPD4692	Approved
0.7473	Intermediate Similarity	NPD4139	Approved
0.7451	Intermediate Similarity	NPD5091	Approved
0.7447	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD4623	Approved
0.7447	Intermediate Similarity	NPD7334	Approved
0.7447	Intermediate Similarity	NPD4519	Discontinued
0.7447	Intermediate Similarity	NPD7146	Approved
0.7447	Intermediate Similarity	NPD6409	Approved
0.7447	Intermediate Similarity	NPD5330	Approved
0.7447	Intermediate Similarity	NPD7521	Approved
0.7423	Intermediate Similarity	NPD5693	Phase 1
0.7423	Intermediate Similarity	NPD7515	Phase 2
0.7412	Intermediate Similarity	NPD4137	Phase 3
0.7407	Intermediate Similarity	NPD4632	Approved
0.74	Intermediate Similarity	NPD5959	Approved
0.7383	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD5167	Approved
0.7326	Intermediate Similarity	NPD4691	Approved
0.7292	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6903	Approved
0.7273	Intermediate Similarity	NPD6868	Approved
0.7263	Intermediate Similarity	NPD6098	Approved
0.7245	Intermediate Similarity	NPD6411	Approved
0.7207	Intermediate Similarity	NPD6317	Approved
0.7207	Intermediate Similarity	NPD6009	Approved
0.7191	Intermediate Similarity	NPD6942	Approved
0.7191	Intermediate Similarity	NPD7339	Approved
0.7158	Intermediate Similarity	NPD1696	Phase 3
0.7143	Intermediate Similarity	NPD6313	Approved
0.7143	Intermediate Similarity	NPD6335	Approved
0.7143	Intermediate Similarity	NPD6314	Approved
0.7128	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4789	Approved
0.7117	Intermediate Similarity	NPD6274	Approved
0.7113	Intermediate Similarity	NPD5208	Approved
0.7111	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7748	Approved
0.7087	Intermediate Similarity	NPD6404	Discontinued
0.708	Intermediate Similarity	NPD7101	Approved
0.708	Intermediate Similarity	NPD7100	Approved
0.7079	Intermediate Similarity	NPD6926	Approved
0.7079	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD7902	Approved
0.7041	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6319	Approved
0.7018	Intermediate Similarity	NPD6054	Approved
0.7009	Intermediate Similarity	NPD6412	Phase 2
0.6989	Remote Similarity	NPD7525	Registered
0.6979	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5983	Phase 2
0.6957	Remote Similarity	NPD6016	Approved
0.6957	Remote Similarity	NPD6015	Approved
0.6941	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7143	Approved
0.6932	Remote Similarity	NPD7144	Approved
0.693	Remote Similarity	NPD4522	Approved
0.6923	Remote Similarity	NPD6933	Approved
0.6897	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5988	Approved
0.6897	Remote Similarity	NPD6370	Approved
0.6889	Remote Similarity	NPD4784	Approved
0.6889	Remote Similarity	NPD4785	Approved
0.687	Remote Similarity	NPD6059	Approved
0.6854	Remote Similarity	NPD7151	Approved
0.6854	Remote Similarity	NPD7152	Approved
0.6854	Remote Similarity	NPD7150	Approved
0.6854	Remote Similarity	NPD4243	Approved
0.6838	Remote Similarity	NPD7604	Phase 2
0.6837	Remote Similarity	NPD3573	Approved
0.6827	Remote Similarity	NPD7638	Approved
0.6818	Remote Similarity	NPD6923	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