NPASS Compound

Structure

CID100267 OpenBabel06191715442D 40 43 0 0 1 0 0 0 0 0999 V2000 -3.7259 -5.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5838 -3.6538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3852 -2.7206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3079 3.8541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1648 3.3595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5113 0.4596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0261 -2.3647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6543 2.8644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8271 2.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3323 -1.7430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0378 -2.6505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3078 0.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6530 0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8271 -0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0204 -4.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4813 2.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4813 1.4319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1344 1.4319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6530 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8271 1.4319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6937 -1.0342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6542 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8271 -0.4775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1344 2.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6764 -3.3592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3079 2.8644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9544 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6542 0.9544 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8274 -1.4315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9536 -4.7768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9915 0.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5103 -0.4946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9882 -0.1268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5113 -0.4949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9813 2.8757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1186 -2.0701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3818 -4.2667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 10 11 1 0 0 0 0 10 18 2 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 17 33 2 0 0 0 0 17 40 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 31 1 1 0 0 0 20 26 1 0 0 0 0 20 34 1 1 0 0 0 21 25 1 0 0 0 0 21 35 1 6 0 0 0 22 29 1 6 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 23 36 2 0 0 0 0 24 31 1 0 0 0 0 24 37 2 0 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 26 38 2 0 0 0 0 27 40 1 0 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 31 8 1 1 0 0 0 32 9 1 6 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.32
Volume:	582.305
LogP:	2.871
LogD:	1.76
LogS:	-4.455
# Rotatable Bonds:	6
TPSA:	138.2
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.265
Synthetic Accessibility Score:	5.399
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.117
MDCK Permeability:	1.4391761396836955e-05
Pgp-inhibitor:	0.973
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.149
20% Bioavailability (F20%):	0.815
30% Bioavailability (F30%):	0.636

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	66.8674545288086%
Volume Distribution (VD):	0.464
Pgp-substrate:	22.445646286010742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.488
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.545

ADMET: Excretion

Clearance (CL):	3.357
Half-life (T1/2):	0.594

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.095
Drug-inuced Liver Injury (DILI):	0.367
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.171
Carcinogencity:	0.894
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.878

Download Data

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

Natural Product: NPC100267

Natural Product ID:	NPC100267
*Common Name:**	[(E,6R)-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-Dihydroxy-4,4,9,13,14-Pentamethyl-3,11-Dioxo-2,7,8,10,12,15,16,17-Octahydro-1H-Cyclopenta[A]Phenanthren-17-Yl]-6-Hydroxy-2-Methyl-5-Oxohept-3-En-2-Yl] Acetate
IUPAC Name:	[(E,6R)-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
Synonyms:
Standard InCHIKey:	IXQKXEUSCPEQRD-DKRGWESNSA-N
Standard InCHI:	InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1
SMILES:	CC(=O)OC(C)(C)/C=C/C(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@@H](C(=O)C4(C)C)O)[C@]3(C)C(=O)C[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508185
PubChem CID:	5281316
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30183289]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33269591]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5523	Picria felterrae	Species	Linderniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15459	Bolbostemma paniculatum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15459	Bolbostemma paniculatum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5523	Picria felterrae	Species	Linderniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21876	Trichosanthes cucumeroides	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	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
GI50	60
IC50	7
Others	1

Activity Type	# Activity
Cell Line	66
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	87.3	nM	PMID[452522]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	14.29	nM	PMID[452522]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	17.54	nM	PMID[452522]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	11.14	nM	PMID[452522]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	167.49	nM	PMID[452522]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	11.22	nM	PMID[452522]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	63.97	nM	PMID[452522]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	24.55	nM	PMID[452522]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	17.42	nM	PMID[452522]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	1396.37	nM	PMID[452522]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	240.99	nM	PMID[452522]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	10.21	nM	PMID[452522]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	36.22	nM	PMID[452522]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	10.0	nM	PMID[452522]
NPT1161	Cell Line	CHO	Cricetulus griseus	IC50	=	1990.0	nM	PMID[452524]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	100.0	nM	PMID[452525]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	100.0	nM	PMID[452525]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12000.0	nM	PMID[452526]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	40.0	nM	PMID[452526]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9720.0	nM	PMID[452526]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1390.0	nM	PMID[452524]
NPT2	Others	Unspecified		Ratio IC50	=	1.43	n.a.	PMID[452524]

☑ 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 NPC100267 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	208
0.1-0.2	1204
0.2-0.3	4021
0.3-0.4	8295
0.4-0.5	12672
0.5-0.6	6215
0.6-0.7	6816
0.7-0.8	2931
0.8-0.85	271
0.85-0.9	50
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475524
0.9717	High Similarity	NPC148458
0.9626	High Similarity	NPC239273
0.9619	High Similarity	NPC221144
0.9537	High Similarity	NPC311554
0.9537	High Similarity	NPC257457
0.9515	High Similarity	NPC475294
0.9266	High Similarity	NPC471854
0.9038	High Similarity	NPC311612
0.8942	High Similarity	NPC87351
0.8899	High Similarity	NPC147180
0.8899	High Similarity	NPC264634
0.8868	High Similarity	NPC196528
0.8868	High Similarity	NPC181265
0.8796	High Similarity	NPC258543
0.8796	High Similarity	NPC241927
0.8796	High Similarity	NPC304495
0.8785	High Similarity	NPC44063
0.8774	High Similarity	NPC235889
0.8727	High Similarity	NPC71348
0.8727	High Similarity	NPC170487
0.8716	High Similarity	NPC473627
0.8679	High Similarity	NPC111323
0.8661	High Similarity	NPC270958
0.8636	High Similarity	NPC231589
0.8636	High Similarity	NPC214797
0.8636	High Similarity	NPC43775
0.8636	High Similarity	NPC118860
0.8624	High Similarity	NPC214644
0.8624	High Similarity	NPC2766
0.8611	High Similarity	NPC185
0.8584	High Similarity	NPC472934
0.8583	High Similarity	NPC471855
0.8559	High Similarity	NPC280782
0.8545	High Similarity	NPC37116
0.8532	High Similarity	NPC177064
0.8532	High Similarity	NPC472825
0.8519	High Similarity	NPC60681
0.8509	High Similarity	NPC118638
0.8491	Intermediate Similarity	NPC224720
0.8491	Intermediate Similarity	NPC476240
0.8491	Intermediate Similarity	NPC476223
0.8491	Intermediate Similarity	NPC474327
0.8482	Intermediate Similarity	NPC122056
0.8482	Intermediate Similarity	NPC202889
0.8482	Intermediate Similarity	NPC472929
0.8476	Intermediate Similarity	NPC222011
0.8476	Intermediate Similarity	NPC176845
0.8476	Intermediate Similarity	NPC197386
0.8468	Intermediate Similarity	NPC474315
0.844	Intermediate Similarity	NPC91034
0.8435	Intermediate Similarity	NPC5292
0.8435	Intermediate Similarity	NPC472933
0.8435	Intermediate Similarity	NPC264954
0.8426	Intermediate Similarity	NPC118911
0.8426	Intermediate Similarity	NPC137657
0.8421	Intermediate Similarity	NPC470959
0.8421	Intermediate Similarity	NPC243065
0.8421	Intermediate Similarity	NPC476965
0.8417	Intermediate Similarity	NPC221414
0.8417	Intermediate Similarity	NPC471407
0.8411	Intermediate Similarity	NPC308351
0.8411	Intermediate Similarity	NPC32577
0.8411	Intermediate Similarity	NPC119601
0.8411	Intermediate Similarity	NPC308726
0.8411	Intermediate Similarity	NPC114540
0.8411	Intermediate Similarity	NPC473928
0.8411	Intermediate Similarity	NPC155332
0.8411	Intermediate Similarity	NPC136289
0.8411	Intermediate Similarity	NPC185530
0.8411	Intermediate Similarity	NPC271266
0.8407	Intermediate Similarity	NPC67259
0.8407	Intermediate Similarity	NPC147912
0.8396	Intermediate Similarity	NPC144956
0.8396	Intermediate Similarity	NPC476274
0.8393	Intermediate Similarity	NPC191620
0.8381	Intermediate Similarity	NPC69385
0.8381	Intermediate Similarity	NPC57416
0.8381	Intermediate Similarity	NPC107243
0.8378	Intermediate Similarity	NPC197428
0.8376	Intermediate Similarity	NPC222688
0.8365	Intermediate Similarity	NPC469599
0.8364	Intermediate Similarity	NPC470269
0.8364	Intermediate Similarity	NPC295244
0.8362	Intermediate Similarity	NPC474370
0.8362	Intermediate Similarity	NPC79579
0.8349	Intermediate Similarity	NPC257353
0.8348	Intermediate Similarity	NPC329736
0.8348	Intermediate Similarity	NPC146786
0.8348	Intermediate Similarity	NPC153440
0.8347	Intermediate Similarity	NPC213634
0.8333	Intermediate Similarity	NPC112009
0.8333	Intermediate Similarity	NPC190286
0.8333	Intermediate Similarity	NPC236390
0.8333	Intermediate Similarity	NPC180204
0.8333	Intermediate Similarity	NPC26478
0.8319	Intermediate Similarity	NPC962
0.8319	Intermediate Similarity	NPC250109
0.8319	Intermediate Similarity	NPC15095
0.8319	Intermediate Similarity	NPC472926
0.8319	Intermediate Similarity	NPC25909
0.8318	Intermediate Similarity	NPC163372
0.8318	Intermediate Similarity	NPC302537
0.8318	Intermediate Similarity	NPC310981
0.8318	Intermediate Similarity	NPC81530
0.8318	Intermediate Similarity	NPC99411
0.8305	Intermediate Similarity	NPC473979
0.8305	Intermediate Similarity	NPC204812
0.8302	Intermediate Similarity	NPC98868
0.8291	Intermediate Similarity	NPC46570
0.8286	Intermediate Similarity	NPC49371
0.8276	Intermediate Similarity	NPC61520
0.8276	Intermediate Similarity	NPC476960
0.8276	Intermediate Similarity	NPC475041
0.8273	Intermediate Similarity	NPC220974
0.8264	Intermediate Similarity	NPC231529
0.8264	Intermediate Similarity	NPC35109
0.8261	Intermediate Similarity	NPC286528
0.8261	Intermediate Similarity	NPC20302
0.8261	Intermediate Similarity	NPC470492
0.8261	Intermediate Similarity	NPC167606
0.8261	Intermediate Similarity	NPC140055
0.8261	Intermediate Similarity	NPC472927
0.8257	Intermediate Similarity	NPC189616
0.825	Intermediate Similarity	NPC470882
0.825	Intermediate Similarity	NPC473265
0.8246	Intermediate Similarity	NPC474181
0.8241	Intermediate Similarity	NPC56498
0.8241	Intermediate Similarity	NPC195290
0.8241	Intermediate Similarity	NPC475320
0.8241	Intermediate Similarity	NPC204450
0.8235	Intermediate Similarity	NPC241456
0.8235	Intermediate Similarity	NPC32868
0.823	Intermediate Similarity	NPC476163
0.8224	Intermediate Similarity	NPC474720
0.822	Intermediate Similarity	NPC153700
0.822	Intermediate Similarity	NPC269642
0.822	Intermediate Similarity	NPC107493
0.822	Intermediate Similarity	NPC88326
0.8214	Intermediate Similarity	NPC16270
0.8211	Intermediate Similarity	NPC469674
0.8208	Intermediate Similarity	NPC253826
0.8208	Intermediate Similarity	NPC18509
0.8208	Intermediate Similarity	NPC475894
0.8208	Intermediate Similarity	NPC474343
0.8205	Intermediate Similarity	NPC476962
0.8205	Intermediate Similarity	NPC109973
0.8205	Intermediate Similarity	NPC476961
0.8205	Intermediate Similarity	NPC474585
0.8198	Intermediate Similarity	NPC94529
0.8198	Intermediate Similarity	NPC220155
0.8197	Intermediate Similarity	NPC220757
0.8197	Intermediate Similarity	NPC196921
0.819	Intermediate Similarity	NPC472932
0.819	Intermediate Similarity	NPC709
0.819	Intermediate Similarity	NPC50774
0.8182	Intermediate Similarity	NPC266570
0.8182	Intermediate Similarity	NPC470267
0.8174	Intermediate Similarity	NPC266728
0.8174	Intermediate Similarity	NPC270929
0.8174	Intermediate Similarity	NPC49492
0.8167	Intermediate Similarity	NPC473635
0.8165	Intermediate Similarity	NPC247957
0.8165	Intermediate Similarity	NPC249187
0.8158	Intermediate Similarity	NPC73300
0.8158	Intermediate Similarity	NPC73050
0.8158	Intermediate Similarity	NPC108721
0.8158	Intermediate Similarity	NPC52634
0.8151	Intermediate Similarity	NPC469789
0.8151	Intermediate Similarity	NPC11895
0.8148	Intermediate Similarity	NPC115899
0.8142	Intermediate Similarity	NPC470960
0.8142	Intermediate Similarity	NPC472928
0.8142	Intermediate Similarity	NPC470961
0.8136	Intermediate Similarity	NPC310511
0.8131	Intermediate Similarity	NPC57079
0.8131	Intermediate Similarity	NPC108368
0.8131	Intermediate Similarity	NPC166745
0.8131	Intermediate Similarity	NPC114274
0.8131	Intermediate Similarity	NPC477854
0.8131	Intermediate Similarity	NPC235464
0.813	Intermediate Similarity	NPC34963
0.8125	Intermediate Similarity	NPC173905
0.8125	Intermediate Similarity	NPC5475
0.8125	Intermediate Similarity	NPC475941
0.8125	Intermediate Similarity	NPC475065
0.8125	Intermediate Similarity	NPC472216
0.8125	Intermediate Similarity	NPC284828
0.8125	Intermediate Similarity	NPC41405
0.8125	Intermediate Similarity	NPC474901
0.812	Intermediate Similarity	NPC305260
0.812	Intermediate Similarity	NPC473270
0.812	Intermediate Similarity	NPC270850
0.8115	Intermediate Similarity	NPC470880
0.8113	Intermediate Similarity	NPC328371
0.8113	Intermediate Similarity	NPC305483
0.8113	Intermediate Similarity	NPC96859
0.8113	Intermediate Similarity	NPC328162
0.8113	Intermediate Similarity	NPC322063
0.8108	Intermediate Similarity	NPC144459

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 NPC100267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1372
0.2-0.3	3623
0.3-0.4	2591
0.4-0.5	836
0.5-0.6	212
0.6-0.7	158
0.7-0.8	111
0.8-0.85	36
0.85-0.9	30
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8981	High Similarity	NPD6649	Approved
0.8981	High Similarity	NPD6650	Approved
0.8899	High Similarity	NPD8297	Approved
0.8879	High Similarity	NPD6881	Approved
0.8879	High Similarity	NPD6899	Approved
0.8807	High Similarity	NPD8130	Phase 1
0.8796	High Similarity	NPD6373	Approved
0.8796	High Similarity	NPD6372	Approved
0.8785	High Similarity	NPD5697	Approved
0.8727	High Similarity	NPD6882	Approved
0.8716	High Similarity	NPD6883	Approved
0.8716	High Similarity	NPD7290	Approved
0.8716	High Similarity	NPD7102	Approved
0.8692	High Similarity	NPD6675	Approved
0.8692	High Similarity	NPD5739	Approved
0.8692	High Similarity	NPD7128	Approved
0.8692	High Similarity	NPD6402	Approved
0.8636	High Similarity	NPD6617	Approved
0.8636	High Similarity	NPD6869	Approved
0.8636	High Similarity	NPD6847	Approved
0.8624	High Similarity	NPD6013	Approved
0.8624	High Similarity	NPD6012	Approved
0.8624	High Similarity	NPD6014	Approved
0.8558	High Similarity	NPD6083	Phase 2
0.8558	High Similarity	NPD6084	Phase 2
0.8532	High Similarity	NPD6011	Approved
0.8532	High Similarity	NPD7320	Approved
0.844	Intermediate Similarity	NPD5701	Approved
0.8411	Intermediate Similarity	NPD5211	Phase 2
0.8396	Intermediate Similarity	NPD4696	Approved
0.8396	Intermediate Similarity	NPD5285	Approved
0.8396	Intermediate Similarity	NPD5286	Approved
0.8302	Intermediate Similarity	NPD5696	Approved
0.8261	Intermediate Similarity	NPD7115	Discovery
0.8257	Intermediate Similarity	NPD5141	Approved
0.8241	Intermediate Similarity	NPD5226	Approved
0.8241	Intermediate Similarity	NPD4633	Approved
0.8241	Intermediate Similarity	NPD5225	Approved
0.8241	Intermediate Similarity	NPD5224	Approved
0.8208	Intermediate Similarity	NPD4755	Approved
0.819	Intermediate Similarity	NPD5695	Phase 3
0.819	Intermediate Similarity	NPD4629	Approved
0.819	Intermediate Similarity	NPD5210	Approved
0.8165	Intermediate Similarity	NPD5174	Approved
0.8165	Intermediate Similarity	NPD5175	Approved
0.8148	Intermediate Similarity	NPD5223	Approved
0.8142	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.812	Intermediate Similarity	NPD7101	Approved
0.812	Intermediate Similarity	NPD7100	Approved
0.8077	Intermediate Similarity	NPD5693	Phase 1
0.8058	Intermediate Similarity	NPD4753	Phase 2
0.8056	Intermediate Similarity	NPD4700	Approved
0.8051	Intermediate Similarity	NPD6319	Approved
0.8036	Intermediate Similarity	NPD4730	Approved
0.8036	Intermediate Similarity	NPD4729	Approved
0.8034	Intermediate Similarity	NPD6335	Approved
0.8017	Intermediate Similarity	NPD6274	Approved
0.8	Intermediate Similarity	NPD4632	Approved
0.7949	Intermediate Similarity	NPD6317	Approved
0.7944	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD5222	Approved
0.7944	Intermediate Similarity	NPD5221	Approved
0.7905	Intermediate Similarity	NPD6079	Approved
0.7895	Intermediate Similarity	NPD5247	Approved
0.7895	Intermediate Similarity	NPD5250	Approved
0.7895	Intermediate Similarity	NPD5248	Approved
0.7895	Intermediate Similarity	NPD5251	Approved
0.7895	Intermediate Similarity	NPD5249	Phase 3
0.7885	Intermediate Similarity	NPD6080	Approved
0.7885	Intermediate Similarity	NPD6904	Approved
0.7885	Intermediate Similarity	NPD6673	Approved
0.7881	Intermediate Similarity	NPD6313	Approved
0.7881	Intermediate Similarity	NPD6314	Approved
0.787	Intermediate Similarity	NPD5173	Approved
0.7857	Intermediate Similarity	NPD4768	Approved
0.7857	Intermediate Similarity	NPD4767	Approved
0.7833	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD6399	Phase 3
0.7798	Intermediate Similarity	NPD7638	Approved
0.7797	Intermediate Similarity	NPD6009	Approved
0.7788	Intermediate Similarity	NPD5737	Approved
0.7788	Intermediate Similarity	NPD6672	Approved
0.7787	Intermediate Similarity	NPD7492	Approved
0.7778	Intermediate Similarity	NPD4697	Phase 3
0.7767	Intermediate Similarity	NPD7521	Approved
0.7767	Intermediate Similarity	NPD7334	Approved
0.7767	Intermediate Similarity	NPD6684	Approved
0.7767	Intermediate Similarity	NPD5330	Approved
0.7767	Intermediate Similarity	NPD7146	Approved
0.7767	Intermediate Similarity	NPD6409	Approved
0.7759	Intermediate Similarity	NPD6053	Discontinued
0.775	Intermediate Similarity	NPD6054	Approved
0.7742	Intermediate Similarity	NPD7736	Approved
0.7739	Intermediate Similarity	NPD4634	Approved
0.7727	Intermediate Similarity	NPD7640	Approved
0.7727	Intermediate Similarity	NPD7639	Approved
0.7724	Intermediate Similarity	NPD6616	Approved
0.7719	Intermediate Similarity	NPD5128	Approved
0.7714	Intermediate Similarity	NPD5328	Approved
0.7712	Intermediate Similarity	NPD6868	Approved
0.7705	Intermediate Similarity	NPD7604	Phase 2
0.7699	Intermediate Similarity	NPD6008	Approved
0.7686	Intermediate Similarity	NPD6908	Approved
0.7686	Intermediate Similarity	NPD5983	Phase 2
0.7686	Intermediate Similarity	NPD6909	Approved
0.7685	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4754	Approved
0.7672	Intermediate Similarity	NPD5215	Approved
0.7672	Intermediate Similarity	NPD5217	Approved
0.7672	Intermediate Similarity	NPD5216	Approved
0.767	Intermediate Similarity	NPD5329	Approved
0.7661	Intermediate Similarity	NPD7078	Approved
0.7642	Intermediate Similarity	NPD5785	Approved
0.7623	Intermediate Similarity	NPD6370	Approved
0.7619	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6903	Approved
0.7596	Intermediate Similarity	NPD5690	Phase 2
0.7596	Intermediate Similarity	NPD6098	Approved
0.7586	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5135	Approved
0.7586	Intermediate Similarity	NPD5169	Approved
0.7581	Intermediate Similarity	NPD7507	Approved
0.7581	Intermediate Similarity	NPD6336	Discontinued
0.7573	Intermediate Similarity	NPD3666	Approved
0.7573	Intermediate Similarity	NPD4197	Approved
0.7573	Intermediate Similarity	NPD3133	Approved
0.7573	Intermediate Similarity	NPD3665	Phase 1
0.757	Intermediate Similarity	NPD5281	Approved
0.757	Intermediate Similarity	NPD5284	Approved
0.757	Intermediate Similarity	NPD6050	Approved
0.757	Intermediate Similarity	NPD5694	Approved
0.7541	Intermediate Similarity	NPD6015	Approved
0.7541	Intermediate Similarity	NPD6016	Approved
0.7521	Intermediate Similarity	NPD5127	Approved
0.752	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD4202	Approved
0.748	Intermediate Similarity	NPD5988	Approved
0.7477	Intermediate Similarity	NPD5692	Phase 3
0.7459	Intermediate Similarity	NPD6059	Approved
0.7431	Intermediate Similarity	NPD7748	Approved
0.7429	Intermediate Similarity	NPD3618	Phase 1
0.7404	Intermediate Similarity	NPD4786	Approved
0.7402	Intermediate Similarity	NPD7319	Approved
0.7387	Intermediate Similarity	NPD7902	Approved
0.7383	Intermediate Similarity	NPD6051	Approved
0.7379	Intermediate Similarity	NPD4221	Approved
0.7379	Intermediate Similarity	NPD4223	Phase 3
0.7333	Intermediate Similarity	NPD1694	Approved
0.7333	Intermediate Similarity	NPD5167	Approved
0.7328	Intermediate Similarity	NPD6614	Approved
0.7321	Intermediate Similarity	NPD4225	Approved
0.7315	Intermediate Similarity	NPD5207	Approved
0.729	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD6001	Approved
0.7265	Intermediate Similarity	NPD6686	Approved
0.7265	Intermediate Similarity	NPD5168	Approved
0.7264	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5280	Approved
0.7264	Intermediate Similarity	NPD5279	Phase 3
0.7264	Intermediate Similarity	NPD4694	Approved
0.7258	Intermediate Similarity	NPD7503	Approved
0.7248	Intermediate Similarity	NPD6411	Approved
0.7248	Intermediate Similarity	NPD7515	Phase 2
0.7212	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3667	Approved
0.7207	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3573	Approved
0.7194	Intermediate Similarity	NPD7236	Approved
0.7179	Intermediate Similarity	NPD6412	Phase 2
0.7179	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5363	Approved
0.7154	Intermediate Similarity	NPD7260	Phase 2
0.7143	Intermediate Similarity	NPD4788	Approved
0.713	Intermediate Similarity	NPD7632	Discontinued
0.713	Intermediate Similarity	NPD5091	Approved
0.712	Intermediate Similarity	NPD8033	Approved
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7900	Approved
0.7103	Intermediate Similarity	NPD4693	Phase 3
0.7103	Intermediate Similarity	NPD4138	Approved
0.7103	Intermediate Similarity	NPD4689	Approved
0.7103	Intermediate Similarity	NPD5205	Approved
0.7103	Intermediate Similarity	NPD5786	Approved
0.7103	Intermediate Similarity	NPD4688	Approved
0.7103	Intermediate Similarity	NPD4690	Approved
0.7091	Intermediate Similarity	NPD8034	Phase 2
0.7091	Intermediate Similarity	NPD8035	Phase 2
0.7087	Intermediate Similarity	NPD4195	Approved
0.7064	Intermediate Similarity	NPD6101	Approved
0.7064	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7239	Suspended
0.7054	Intermediate Similarity	NPD5654	Approved
0.7048	Intermediate Similarity	NPD6435	Approved
0.704	Intermediate Similarity	NPD8294	Approved
0.704	Intermediate Similarity	NPD8377	Approved
0.7027	Intermediate Similarity	NPD5779	Approved
0.7027	Intermediate Similarity	NPD5778	Approved
0.7019	Intermediate Similarity	NPD4695	Discontinued
0.7016	Intermediate Similarity	NPD7327	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