NPASS Compound

Structure

CID46981 OpenBabel06191715382D 30 35 0 0 1 0 0 0 0 0999 V2000 -4.9594 1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3725 2.1916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5338 -0.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5590 2.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 -2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 -2.4371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 2.3286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2220 -1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 -0.9736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3784 -2.9239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6891 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3812 0.5481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9544 1.3357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0481 1.4400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5343 -2.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2222 -2.4361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8450 -1.4619 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6894 -0.9741 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9746 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0170 1.5410 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6879 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8447 0.4873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5340 -1.4614 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 -2.4124 0.6507 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.0885 -2.9357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 1.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 8 1 0 0 0 0 5 15 1 0 0 0 0 6 7 1 0 0 0 0 6 17 2 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 26 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 12 23 1 0 0 0 0 13 20 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 1 1 1 0 0 0 16 2 1 1 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 6 0 0 0 19 7 1 1 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 6 0 0 0 21 27 1 6 0 0 0 22 28 1 6 0 0 0 23 25 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 1 0 0 0 24 30 1 0 0 0 0 25 27 1 6 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	413.33
Volume:	450.15
LogP:	4.532
LogD:	4.504
LogS:	-4.428
# Rotatable Bonds:	0
TPSA:	43.7
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	5.084
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.815
MDCK Permeability:	1.1317462849547155e-05
Pgp-inhibitor:	0.347
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.094
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.56
Plasma Protein Binding (PPB):	78.72110748291016%
Volume Distribution (VD):	1.947
Pgp-substrate:	14.322638511657715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.64
CYP2D6-substrate:	0.791
CYP3A4-inhibitor:	0.656
CYP3A4-substrate:	0.631

ADMET: Excretion

Clearance (CL):	13.8
Half-life (T1/2):	0.471

ADMET: Toxicity

hERG Blockers:	0.418
Human Hepatotoxicity (H-HT):	0.442
Drug-inuced Liver Injury (DILI):	0.245
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.706
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.921
Carcinogencity:	0.593
Eye Corrosion:	0.048
Eye Irritation:	0.019
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC46981

Natural Product ID:	NPC46981
*Common Name:**	AANKDJLVHZQCFG-KVHNBARJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AANKDJLVHZQCFG-KVHNBARJSA-N
Standard InCHI:	InChI=1S/C27H43NO2/c1-15-5-8-22-16(2)25-23(28(22)14-15)12-21-19-7-6-17-11-18(29)9-10-26(17,3)20(19)13-24(30)27(21,25)4/h6,15-16,18-25,29-30H,5,7-14H2,1-4H3/t15-,16+,18-,19+,20-,21-,22+,23-,24-,25-,26-,27+/m0/s1
SMILES:	C[C@H]1CC[C@@H]2[C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5C[C@@H]([C@]34C)O)O)N2C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1993702
PubChem CID:	253295
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0001703] Solanidines 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
NPO1073	Phlomis samia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520237]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	Roots	n.a.	n.a.	PMID[2089115]
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[24689280]
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24689280]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	roots and rhizomes	n.a.	n.a.	PMID[25835537]
NPO11185	Hohenbuehelia grisea	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29356520]
NPO4250	Gloriosa superba	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32372642]
NPO2634	Tetrapleura tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8289059]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO4250	Gloriosa superba	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10815	Uncaria borneensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4250	Gloriosa superba	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10815	Uncaria borneensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5651	Veratrum oxysepalum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9596	Baeria coronaria	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13582	Leucopaxillus giganteus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1073	Phlomis samia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7675	Perezia cuernavacana	Species	Pereziidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5651	Veratrum oxysepalum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1968	Delphinium ternatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12144	Fontanesia phillyreoides	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15380	Melicope ternata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8057	Bulnesia retama	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5237	Stevia isomeca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4148	Artemisia spicigera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9049	Tanacetum parthenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11380	Neurolaena macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO612	Pteronia stricta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4347	Artemisia chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12742	Botryotrichum peruvianum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9242	Bauhinia manca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1718	Sarcodontia setosa	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4373	Phyllanthus acuminatus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2634	Tetrapleura tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14649	Thais orbita	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10815	Uncaria borneensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20796	Stemonoporus canaliculatus	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9373	Sigmadocia symbiotica	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4179	Uta tuberculata	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11185	Hohenbuehelia grisea	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4250	Gloriosa superba	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	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	58

Activity Type	# Activity
Cell Line	58

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[573952]

☑ 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 NPC46981 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	107
0.1-0.2	1010
0.2-0.3	10584
0.3-0.4	15768
0.4-0.5	8123
0.5-0.6	5656
0.6-0.7	1348
0.7-0.8	88
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC91604
0.8835	High Similarity	NPC212874
0.8515	High Similarity	NPC289140
0.844	Intermediate Similarity	NPC476498
0.8288	Intermediate Similarity	NPC476499
0.8286	Intermediate Similarity	NPC176012
0.8257	Intermediate Similarity	NPC287764
0.8252	Intermediate Similarity	NPC474164
0.8165	Intermediate Similarity	NPC147835
0.8165	Intermediate Similarity	NPC85001
0.8165	Intermediate Similarity	NPC95920
0.8165	Intermediate Similarity	NPC253645
0.8036	Intermediate Similarity	NPC478137
0.7905	Intermediate Similarity	NPC140300
0.789	Intermediate Similarity	NPC86906
0.7879	Intermediate Similarity	NPC75810
0.781	Intermediate Similarity	NPC476903
0.7798	Intermediate Similarity	NPC475239
0.7739	Intermediate Similarity	NPC28280
0.7739	Intermediate Similarity	NPC304646
0.7615	Intermediate Similarity	NPC50815
0.7603	Intermediate Similarity	NPC265275
0.7603	Intermediate Similarity	NPC94881
0.7603	Intermediate Similarity	NPC48886
0.7563	Intermediate Similarity	NPC476504
0.7544	Intermediate Similarity	NPC79238
0.7521	Intermediate Similarity	NPC476503
0.75	Intermediate Similarity	NPC478138
0.7455	Intermediate Similarity	NPC471083
0.7455	Intermediate Similarity	NPC247060
0.7453	Intermediate Similarity	NPC280710
0.7453	Intermediate Similarity	NPC243985
0.7434	Intermediate Similarity	NPC159367
0.7407	Intermediate Similarity	NPC240650
0.7387	Intermediate Similarity	NPC241879
0.7358	Intermediate Similarity	NPC93027
0.7345	Intermediate Similarity	NPC25340
0.7345	Intermediate Similarity	NPC169375
0.7273	Intermediate Similarity	NPC238323
0.7232	Intermediate Similarity	NPC45365
0.7232	Intermediate Similarity	NPC474583
0.7232	Intermediate Similarity	NPC293299
0.7222	Intermediate Similarity	NPC272732
0.7222	Intermediate Similarity	NPC311164
0.7179	Intermediate Similarity	NPC56796
0.7172	Intermediate Similarity	NPC275910
0.717	Intermediate Similarity	NPC84171
0.7157	Intermediate Similarity	NPC171639
0.7143	Intermediate Similarity	NPC240604
0.7143	Intermediate Similarity	NPC300324
0.7143	Intermediate Similarity	NPC321381
0.7143	Intermediate Similarity	NPC107059
0.7143	Intermediate Similarity	NPC321016
0.7143	Intermediate Similarity	NPC189883
0.7129	Intermediate Similarity	NPC474531
0.712	Intermediate Similarity	NPC317654
0.712	Intermediate Similarity	NPC96010
0.7117	Intermediate Similarity	NPC135799
0.7117	Intermediate Similarity	NPC275686
0.7105	Intermediate Similarity	NPC55462
0.71	Intermediate Similarity	NPC1319
0.7087	Intermediate Similarity	NPC209802
0.7071	Intermediate Similarity	NPC198968
0.7071	Intermediate Similarity	NPC318495
0.7071	Intermediate Similarity	NPC214570
0.7071	Intermediate Similarity	NPC155986
0.7059	Intermediate Similarity	NPC248886
0.7043	Intermediate Similarity	NPC8009
0.7043	Intermediate Similarity	NPC83047
0.7043	Intermediate Similarity	NPC267217
0.7043	Intermediate Similarity	NPC48127
0.7041	Intermediate Similarity	NPC304309
0.7041	Intermediate Similarity	NPC141071
0.7041	Intermediate Similarity	NPC471723
0.7041	Intermediate Similarity	NPC134847
0.7041	Intermediate Similarity	NPC162742
0.7041	Intermediate Similarity	NPC257347
0.7041	Intermediate Similarity	NPC136188
0.7041	Intermediate Similarity	NPC22105
0.7041	Intermediate Similarity	NPC285893
0.7041	Intermediate Similarity	NPC288035
0.7041	Intermediate Similarity	NPC230301
0.7041	Intermediate Similarity	NPC28657
0.703	Intermediate Similarity	NPC236112
0.7009	Intermediate Similarity	NPC472313
0.7009	Intermediate Similarity	NPC472359
0.7009	Intermediate Similarity	NPC139778
0.7	Intermediate Similarity	NPC285761
0.7	Intermediate Similarity	NPC138621
0.7	Intermediate Similarity	NPC244385
0.7	Intermediate Similarity	NPC6978
0.7	Intermediate Similarity	NPC473943
0.7	Intermediate Similarity	NPC477522
0.7	Intermediate Similarity	NPC474216
0.7	Intermediate Similarity	NPC167037
0.7	Intermediate Similarity	NPC87604
0.697	Remote Similarity	NPC46160
0.697	Remote Similarity	NPC113733
0.697	Remote Similarity	NPC237460
0.697	Remote Similarity	NPC73875
0.697	Remote Similarity	NPC134330
0.697	Remote Similarity	NPC202642
0.697	Remote Similarity	NPC129165
0.6961	Remote Similarity	NPC470383
0.6961	Remote Similarity	NPC109533
0.696	Remote Similarity	NPC296686
0.6957	Remote Similarity	NPC477292
0.6952	Remote Similarity	NPC24277
0.6949	Remote Similarity	NPC474459
0.6931	Remote Similarity	NPC80530
0.6931	Remote Similarity	NPC273410
0.6931	Remote Similarity	NPC209430
0.6931	Remote Similarity	NPC109546
0.6931	Remote Similarity	NPC81306
0.6931	Remote Similarity	NPC28862
0.6931	Remote Similarity	NPC84694
0.6931	Remote Similarity	NPC328714
0.6931	Remote Similarity	NPC47982
0.6931	Remote Similarity	NPC30986
0.6931	Remote Similarity	NPC143182
0.693	Remote Similarity	NPC90538
0.693	Remote Similarity	NPC473254
0.6923	Remote Similarity	NPC274895
0.6923	Remote Similarity	NPC124172
0.6909	Remote Similarity	NPC155985
0.6903	Remote Similarity	NPC118275
0.69	Remote Similarity	NPC34019
0.6899	Remote Similarity	NPC15249
0.6899	Remote Similarity	NPC25455
0.6893	Remote Similarity	NPC470049
0.6893	Remote Similarity	NPC49964
0.6893	Remote Similarity	NPC101462
0.6893	Remote Similarity	NPC5985
0.6893	Remote Similarity	NPC30166
0.6893	Remote Similarity	NPC201852
0.6893	Remote Similarity	NPC20853
0.6891	Remote Similarity	NPC124358
0.6891	Remote Similarity	NPC474452
0.6869	Remote Similarity	NPC121744
0.6869	Remote Similarity	NPC118508
0.6869	Remote Similarity	NPC322353
0.6863	Remote Similarity	NPC164840
0.6863	Remote Similarity	NPC26117
0.6863	Remote Similarity	NPC234193
0.6863	Remote Similarity	NPC236237
0.6863	Remote Similarity	NPC13554
0.6863	Remote Similarity	NPC102253
0.6863	Remote Similarity	NPC322313
0.6863	Remote Similarity	NPC241290
0.6863	Remote Similarity	NPC209944
0.686	Remote Similarity	NPC470538
0.6852	Remote Similarity	NPC312637
0.685	Remote Similarity	NPC470537
0.6846	Remote Similarity	NPC122819
0.6832	Remote Similarity	NPC474989
0.6832	Remote Similarity	NPC18603
0.6832	Remote Similarity	NPC85346
0.6832	Remote Similarity	NPC99168
0.6832	Remote Similarity	NPC76931
0.6832	Remote Similarity	NPC307965
0.6832	Remote Similarity	NPC22955
0.6832	Remote Similarity	NPC205455
0.6832	Remote Similarity	NPC470396
0.6832	Remote Similarity	NPC65897
0.6832	Remote Similarity	NPC186191
0.6832	Remote Similarity	NPC302041
0.6827	Remote Similarity	NPC317458
0.6822	Remote Similarity	NPC470542
0.68	Remote Similarity	NPC7214
0.68	Remote Similarity	NPC96319
0.68	Remote Similarity	NPC470362
0.6796	Remote Similarity	NPC474731
0.6796	Remote Similarity	NPC264245
0.6796	Remote Similarity	NPC474683
0.6796	Remote Similarity	NPC7505
0.6796	Remote Similarity	NPC474752
0.6796	Remote Similarity	NPC23852
0.6796	Remote Similarity	NPC209620
0.6796	Remote Similarity	NPC47761
0.6796	Remote Similarity	NPC82986
0.6796	Remote Similarity	NPC474759
0.6794	Remote Similarity	NPC147753
0.6794	Remote Similarity	NPC150057
0.6792	Remote Similarity	NPC474970
0.6792	Remote Similarity	NPC261266
0.6792	Remote Similarity	NPC94462
0.6792	Remote Similarity	NPC6391
0.6768	Remote Similarity	NPC243342
0.6768	Remote Similarity	NPC477138
0.6768	Remote Similarity	NPC100334
0.6765	Remote Similarity	NPC53744
0.6765	Remote Similarity	NPC291379
0.6765	Remote Similarity	NPC472463
0.6762	Remote Similarity	NPC478102
0.6762	Remote Similarity	NPC470077
0.6762	Remote Similarity	NPC185568
0.6762	Remote Similarity	NPC205845
0.6759	Remote Similarity	NPC105495
0.6748	Remote Similarity	NPC476952
0.6733	Remote Similarity	NPC101475

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 NPC46981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	106
0.1-0.2	627
0.2-0.3	3568
0.3-0.4	3512
0.4-0.5	938
0.5-0.6	335
0.6-0.7	63
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7041	Intermediate Similarity	NPD7339	Approved
0.7041	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD7755	Approved
0.7	Intermediate Similarity	NPD7754	Approved
0.6863	Remote Similarity	NPD7525	Registered
0.6846	Remote Similarity	NPD8449	Approved
0.68	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD8450	Suspended
0.6667	Remote Similarity	NPD7333	Discontinued
0.6604	Remote Similarity	NPD4786	Approved
0.6602	Remote Similarity	NPD7645	Phase 2
0.6549	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7920	Phase 3
0.6491	Remote Similarity	NPD7919	Phase 3
0.6475	Remote Similarity	NPD7335	Phase 2
0.6475	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7336	Phase 2
0.6455	Remote Similarity	NPD5328	Approved
0.6436	Remote Similarity	NPD6924	Approved
0.6436	Remote Similarity	NPD6926	Approved
0.6435	Remote Similarity	NPD8088	Phase 1
0.6415	Remote Similarity	NPD3667	Approved
0.6339	Remote Similarity	NPD6079	Approved
0.6333	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3618	Phase 1
0.6311	Remote Similarity	NPD6933	Approved
0.6275	Remote Similarity	NPD4785	Approved
0.6275	Remote Similarity	NPD4784	Approved
0.6273	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4243	Approved
0.6238	Remote Similarity	NPD7152	Approved
0.6238	Remote Similarity	NPD7150	Approved
0.6238	Remote Similarity	NPD7151	Approved
0.6226	Remote Similarity	NPD4748	Discontinued
0.621	Remote Similarity	NPD8077	Approved
0.621	Remote Similarity	NPD8078	Approved
0.6202	Remote Similarity	NPD6908	Approved
0.6202	Remote Similarity	NPD6909	Approved
0.62	Remote Similarity	NPD6922	Approved
0.62	Remote Similarity	NPD6923	Approved
0.6172	Remote Similarity	NPD7517	Approved
0.6172	Remote Similarity	NPD7519	Approved
0.6172	Remote Similarity	NPD7518	Approved
0.614	Remote Similarity	NPD4202	Approved
0.6139	Remote Similarity	NPD7144	Approved
0.6139	Remote Similarity	NPD7143	Approved
0.6132	Remote Similarity	NPD6929	Approved
0.6116	Remote Similarity	NPD6920	Discontinued
0.6091	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5771	Approved
0.6075	Remote Similarity	NPD6930	Phase 2
0.6075	Remote Similarity	NPD7509	Discontinued
0.6075	Remote Similarity	NPD6931	Approved
0.6034	Remote Similarity	NPD7991	Discontinued
0.6016	Remote Similarity	NPD6415	Discontinued
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD6399	Phase 3
0.5983	Remote Similarity	NPD5221	Approved
0.5983	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4697	Phase 3
0.5983	Remote Similarity	NPD5222	Approved
0.595	Remote Similarity	NPD7986	Approved
0.595	Remote Similarity	NPD7911	Approved
0.595	Remote Similarity	NPD7987	Approved
0.595	Remote Similarity	NPD7912	Approved
0.5943	Remote Similarity	NPD6925	Approved
0.5943	Remote Similarity	NPD5776	Phase 2
0.5943	Remote Similarity	NPD6932	Approved
0.5932	Remote Similarity	NPD5173	Approved
0.5932	Remote Similarity	NPD4755	Approved
0.5929	Remote Similarity	NPD4723	Approved
0.5929	Remote Similarity	NPD4722	Approved
0.5923	Remote Similarity	NPD7522	Discontinued
0.5913	Remote Similarity	NPD7515	Phase 2
0.5909	Remote Similarity	NPD6695	Phase 3
0.5909	Remote Similarity	NPD7725	Approved
0.5905	Remote Similarity	NPD4190	Phase 3
0.5905	Remote Similarity	NPD5275	Approved
0.5888	Remote Similarity	NPD7145	Approved
0.5887	Remote Similarity	NPD6334	Approved
0.5887	Remote Similarity	NPD6333	Approved
0.5865	Remote Similarity	NPD7122	Discontinued
0.5856	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3668	Phase 3
0.5855	Remote Similarity	NPD5743	Approved
0.5855	Remote Similarity	NPD5741	Approved
0.5855	Remote Similarity	NPD5742	Approved
0.5854	Remote Similarity	NPD8040	Discontinued
0.5833	Remote Similarity	NPD8418	Phase 2
0.5833	Remote Similarity	NPD4195	Approved
0.5833	Remote Similarity	NPD6683	Phase 2
0.5833	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD4700	Approved
0.5833	Remote Similarity	NPD5286	Approved
0.5833	Remote Similarity	NPD4696	Approved
0.5806	Remote Similarity	NPD7989	Approved
0.5806	Remote Similarity	NPD7990	Approved
0.5804	Remote Similarity	NPD6893	Approved
0.5794	Remote Similarity	NPD6420	Discontinued
0.5789	Remote Similarity	NPD4121	Phase 3
0.5789	Remote Similarity	NPD4120	Approved
0.5785	Remote Similarity	NPD5223	Approved
0.5785	Remote Similarity	NPD4159	Approved
0.578	Remote Similarity	NPD7514	Phase 3
0.576	Remote Similarity	NPD7320	Approved
0.5755	Remote Similarity	NPD8264	Approved
0.5752	Remote Similarity	NPD8308	Discontinued
0.5752	Remote Similarity	NPD5279	Phase 3
0.575	Remote Similarity	NPD7638	Approved
0.575	Remote Similarity	NPD5290	Discontinued
0.5741	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD4753	Phase 2
0.5738	Remote Similarity	NPD4719	Phase 2
0.5738	Remote Similarity	NPD5226	Approved
0.5738	Remote Similarity	NPD5225	Approved
0.5738	Remote Similarity	NPD5224	Approved
0.5738	Remote Similarity	NPD5211	Phase 2
0.5738	Remote Similarity	NPD4633	Approved
0.5727	Remote Similarity	NPD6902	Approved
0.5726	Remote Similarity	NPD5739	Approved
0.5726	Remote Similarity	NPD6675	Approved
0.5726	Remote Similarity	NPD7128	Approved
0.5726	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD3638	Discontinued
0.5702	Remote Similarity	NPD7639	Approved
0.5702	Remote Similarity	NPD7524	Approved
0.5702	Remote Similarity	NPD7640	Approved
0.5702	Remote Similarity	NPD7750	Discontinued
0.5691	Remote Similarity	NPD5174	Approved
0.5691	Remote Similarity	NPD4754	Approved
0.5691	Remote Similarity	NPD5175	Approved
0.5678	Remote Similarity	NPD7748	Approved
0.5676	Remote Similarity	NPD4221	Approved
0.5676	Remote Similarity	NPD4223	Phase 3
0.5664	Remote Similarity	NPD5329	Approved
0.5659	Remote Similarity	NPD8298	Phase 2
0.5645	Remote Similarity	NPD5141	Approved
0.5643	Remote Similarity	NPD6845	Suspended
0.5641	Remote Similarity	NPD8034	Phase 2
0.5641	Remote Similarity	NPD8035	Phase 2
0.5636	Remote Similarity	NPD7332	Phase 2
0.5635	Remote Similarity	NPD6899	Approved
0.5635	Remote Similarity	NPD6881	Approved
0.56	Remote Similarity	NPD4768	Approved
0.56	Remote Similarity	NPD4767	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