NPASS Compound

Structure

CID322353 OpenBabel06191716162D 31 34 0 0 1 0 0 0 0 0999 V2000 -1.4614 5.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0016 5.2038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6689 4.1115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2727 3.2223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3763 -2.9580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 0.5234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2092 3.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8129 2.5360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6886 -1.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6871 0.9735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6877 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2190 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3754 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6868 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0334 5.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6372 4.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 2.4345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3760 -1.9481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 1.4610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5324 -1.4611 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6880 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 -0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2193 -1.4606 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5321 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0854 -1.9603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 21 4 1 1 0 0 0 21 23 1 0 0 0 0 22 5 1 1 0 0 0 22 24 1 0 0 0 0 22 27 1 0 0 0 0 23 29 1 6 0 0 0 24 28 1 0 0 0 0 25 26 2 0 0 0 0 25 28 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 6 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	496.727
LogP:	7.142
LogD:	5.795
LogS:	-6.66
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	4.759
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.827
MDCK Permeability:	1.012401935440721e-05
Pgp-inhibitor:	0.941
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.683

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	93.06706237792969%
Volume Distribution (VD):	2.006
Pgp-substrate:	1.6105085611343384%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.646
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.978
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.438
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.796
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	7.069
Half-life (T1/2):	0.022

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.528
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.091
Skin Sensitization:	0.429
Carcinogencity:	0.051
Eye Corrosion:	0.08
Eye Irritation:	0.213
Respiratory Toxicity:	0.364

Download Data

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

Natural Product: NPC322353

Natural Product ID:	NPC322353
*Common Name:**	(3S,4S,10S,13R,14R,17R)-4,10,13,14-Tetramethyl-17-[(2R)-6-Methyl-5-Methylideneheptan-2-Yl]-1,2,3,4,5,6,7,11,12,15,16,17-Dodecahydrocyclopenta[A]Phenanthren-3-Ol
IUPAC Name:	(3S,4S,10S,13R,14R,17R)-4,10,13,14-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,5,6,7,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	MMNYKQIDRZNIKT-YLANKJTKSA-N
Standard InCHI:	InChI=1S/C30H50O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h19,21-24,27,31H,3,9-18H2,1-2,4-8H3/t21-,22+,23-,24?,27+,28+,29-,30+/m1/s1
SMILES:	CC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CCC2[C@]1(C)CC[C@@H]([C@H]2C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1978954
PubChem CID:	390622
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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	55

Activity Type	# Activity
Cell Line	55

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	1435.49	nM	PMID[448436]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	1172.2	nM	PMID[448436]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	1279.38	nM	PMID[448436]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	1383.57	nM	PMID[448436]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	1233.1	nM	PMID[448436]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	1183.04	nM	PMID[448436]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	360.58	nM	PMID[448436]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	1468.93	nM	PMID[448436]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	1256.03	nM	PMID[448436]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	1288.25	nM	PMID[448436]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	272.9	nM	PMID[448436]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	1406.05	nM	PMID[448436]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	1774.19	nM	PMID[448436]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	952.8	nM	PMID[448436]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	879.02	nM	PMID[448436]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	1396.37	nM	PMID[448436]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	1389.95	nM	PMID[448436]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	1422.33	nM	PMID[448436]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	1614.36	nM	PMID[448436]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	1499.68	nM	PMID[448436]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	2172.7	nM	PMID[448436]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	1348.96	nM	PMID[448436]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	1006.93	nM	PMID[448436]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	1706.08	nM	PMID[448436]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	1261.83	nM	PMID[448436]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	1172.2	nM	PMID[448436]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	1199.5	nM	PMID[448436]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	1599.56	nM	PMID[448436]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	905.73	nM	PMID[448436]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	1475.71	nM	PMID[448436]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	1555.97	nM	PMID[448436]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	1202.26	nM	PMID[448436]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	1250.26	nM	PMID[448436]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	1531.09	nM	PMID[448436]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	1199.5	nM	PMID[448436]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	1312.2	nM	PMID[448436]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	1465.55	nM	PMID[448436]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	1227.44	nM	PMID[448436]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	1073.99	nM	PMID[448436]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	1599.56	nM	PMID[448436]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	679.2	nM	PMID[448436]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	1432.19	nM	PMID[448436]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	1145.51	nM	PMID[448436]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	1324.34	nM	PMID[448436]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	1078.95	nM	PMID[448436]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2349.63	nM	PMID[448436]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	1603.25	nM	PMID[448436]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	1485.94	nM	PMID[448436]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	984.01	nM	PMID[448436]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	414.0	nM	PMID[448436]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	1807.17	nM	PMID[448436]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	479.73	nM	PMID[448436]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	1282.33	nM	PMID[448436]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	1370.88	nM	PMID[448436]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	1174.9	nM	PMID[448436]

☑ 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 NPC322353 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	149
0.1-0.2	1621
0.2-0.3	9314
0.3-0.4	15213
0.4-0.5	6400
0.5-0.6	5829
0.6-0.7	3047
0.7-0.8	906
0.8-0.85	141
0.85-0.9	48
0.9-0.95	14
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC118508
1.0	High Similarity	NPC121744
0.9857	High Similarity	NPC202642
0.9857	High Similarity	NPC73875
0.9857	High Similarity	NPC46160
0.9718	High Similarity	NPC214570
0.971	High Similarity	NPC201373
0.9583	High Similarity	NPC205455
0.9583	High Similarity	NPC186191
0.9583	High Similarity	NPC275910
0.9577	High Similarity	NPC470362
0.9577	High Similarity	NPC189883
0.9437	High Similarity	NPC257347
0.9437	High Similarity	NPC471723
0.9437	High Similarity	NPC141071
0.9315	High Similarity	NPC318136
0.9306	High Similarity	NPC237460
0.9306	High Similarity	NPC300324
0.9306	High Similarity	NPC129165
0.9306	High Similarity	NPC240604
0.9306	High Similarity	NPC134330
0.9189	High Similarity	NPC1319
0.9167	High Similarity	NPC162742
0.9167	High Similarity	NPC304309
0.9167	High Similarity	NPC134847
0.9167	High Similarity	NPC288035
0.9167	High Similarity	NPC285893
0.9167	High Similarity	NPC28657
0.9167	High Similarity	NPC136188
0.9167	High Similarity	NPC230301
0.9167	High Similarity	NPC22105
0.9079	High Similarity	NPC87489
0.9079	High Similarity	NPC202389
0.9079	High Similarity	NPC201852
0.9067	High Similarity	NPC236112
0.9054	High Similarity	NPC138621
0.9054	High Similarity	NPC6978
0.9054	High Similarity	NPC85346
0.9054	High Similarity	NPC167037
0.9054	High Similarity	NPC285761
0.9054	High Similarity	NPC302041
0.9054	High Similarity	NPC65897
0.9054	High Similarity	NPC244385
0.9041	High Similarity	NPC321016
0.9041	High Similarity	NPC113733
0.9041	High Similarity	NPC107059
0.9041	High Similarity	NPC321381
0.9028	High Similarity	NPC469533
0.9028	High Similarity	NPC469534
0.9028	High Similarity	NPC469593
0.9014	High Similarity	NPC111234
0.9014	High Similarity	NPC110799
0.8947	High Similarity	NPC474531
0.8947	High Similarity	NPC6707
0.8933	High Similarity	NPC30986
0.8933	High Similarity	NPC209430
0.8933	High Similarity	NPC273410
0.8933	High Similarity	NPC80530
0.8919	High Similarity	NPC198968
0.8919	High Similarity	NPC318495
0.8919	High Similarity	NPC155986
0.8919	High Similarity	NPC34019
0.8889	High Similarity	NPC182717
0.8889	High Similarity	NPC474140
0.8873	High Similarity	NPC45296
0.8846	High Similarity	NPC231310
0.8831	High Similarity	NPC20853
0.8831	High Similarity	NPC470049
0.8831	High Similarity	NPC30166
0.8816	High Similarity	NPC102253
0.8816	High Similarity	NPC322313
0.8816	High Similarity	NPC22403
0.8816	High Similarity	NPC236237
0.8816	High Similarity	NPC13554
0.88	High Similarity	NPC474216
0.88	High Similarity	NPC87604
0.88	High Similarity	NPC473943
0.88	High Similarity	NPC307965
0.88	High Similarity	NPC312328
0.88	High Similarity	NPC18603
0.88	High Similarity	NPC477522
0.88	High Similarity	NPC76931
0.8784	High Similarity	NPC244488
0.8784	High Similarity	NPC247325
0.8767	High Similarity	NPC5046
0.8767	High Similarity	NPC145552
0.8767	High Similarity	NPC254509
0.8767	High Similarity	NPC25511
0.8767	High Similarity	NPC192638
0.8767	High Similarity	NPC62657
0.8767	High Similarity	NPC100334
0.8767	High Similarity	NPC49168
0.8767	High Similarity	NPC196358
0.8701	High Similarity	NPC470383
0.8684	High Similarity	NPC81306
0.8684	High Similarity	NPC143182
0.8684	High Similarity	NPC328714
0.8684	High Similarity	NPC109546
0.8684	High Similarity	NPC28862
0.8684	High Similarity	NPC47982
0.8684	High Similarity	NPC84694
0.8649	High Similarity	NPC240235
0.8649	High Similarity	NPC200243
0.8649	High Similarity	NPC104387
0.8649	High Similarity	NPC178383
0.8649	High Similarity	NPC185536
0.8649	High Similarity	NPC231256
0.8649	High Similarity	NPC230704
0.8649	High Similarity	NPC3403
0.8649	High Similarity	NPC70982
0.8649	High Similarity	NPC471468
0.8649	High Similarity	NPC212879
0.863	High Similarity	NPC195489
0.8625	High Similarity	NPC94755
0.8625	High Similarity	NPC28252
0.8625	High Similarity	NPC55309
0.8625	High Similarity	NPC72133
0.8608	High Similarity	NPC470077
0.8608	High Similarity	NPC209802
0.8608	High Similarity	NPC124172
0.8608	High Similarity	NPC478102
0.8608	High Similarity	NPC238485
0.8592	High Similarity	NPC208999
0.8592	High Similarity	NPC160209
0.859	High Similarity	NPC248886
0.859	High Similarity	NPC101462
0.859	High Similarity	NPC296701
0.859	High Similarity	NPC49964
0.859	High Similarity	NPC218616
0.859	High Similarity	NPC7988
0.8571	High Similarity	NPC234193
0.8571	High Similarity	NPC164840
0.8571	High Similarity	NPC241290
0.8571	High Similarity	NPC26117
0.8571	High Similarity	NPC209944
0.8553	High Similarity	NPC477514
0.8533	High Similarity	NPC78067
0.8533	High Similarity	NPC96319
0.8533	High Similarity	NPC120098
0.8533	High Similarity	NPC265328
0.8533	High Similarity	NPC91573
0.8533	High Similarity	NPC290598
0.8533	High Similarity	NPC86305
0.8533	High Similarity	NPC122418
0.8533	High Similarity	NPC27765
0.8533	High Similarity	NPC14112
0.8533	High Similarity	NPC30590
0.8533	High Similarity	NPC278091
0.8533	High Similarity	NPC93662
0.8519	High Similarity	NPC187376
0.8519	High Similarity	NPC159046
0.8519	High Similarity	NPC233836
0.8519	High Similarity	NPC475772
0.8514	High Similarity	NPC308440
0.8514	High Similarity	NPC91858
0.8514	High Similarity	NPC477138
0.8514	High Similarity	NPC472503
0.8514	High Similarity	NPC243342
0.85	High Similarity	NPC318390
0.8493	Intermediate Similarity	NPC167706
0.8481	Intermediate Similarity	NPC207013
0.8481	Intermediate Similarity	NPC477818
0.8481	Intermediate Similarity	NPC132635
0.8481	Intermediate Similarity	NPC110778
0.8481	Intermediate Similarity	NPC470384
0.8481	Intermediate Similarity	NPC113978
0.8481	Intermediate Similarity	NPC317458
0.8462	Intermediate Similarity	NPC474752
0.8462	Intermediate Similarity	NPC7505
0.8462	Intermediate Similarity	NPC209620
0.8462	Intermediate Similarity	NPC264245
0.8462	Intermediate Similarity	NPC474683
0.8462	Intermediate Similarity	NPC474731
0.8462	Intermediate Similarity	NPC82986
0.8462	Intermediate Similarity	NPC47761
0.8462	Intermediate Similarity	NPC474759
0.8462	Intermediate Similarity	NPC23852
0.8442	Intermediate Similarity	NPC472463
0.8421	Intermediate Similarity	NPC40394
0.8421	Intermediate Similarity	NPC248830
0.8421	Intermediate Similarity	NPC212241
0.8421	Intermediate Similarity	NPC157996
0.8421	Intermediate Similarity	NPC202540
0.8421	Intermediate Similarity	NPC471798
0.8421	Intermediate Similarity	NPC119355
0.8421	Intermediate Similarity	NPC472805
0.8421	Intermediate Similarity	NPC101475
0.8421	Intermediate Similarity	NPC34177
0.8421	Intermediate Similarity	NPC90979
0.8421	Intermediate Similarity	NPC331618
0.8421	Intermediate Similarity	NPC257191
0.8415	Intermediate Similarity	NPC242864
0.8415	Intermediate Similarity	NPC470542
0.8415	Intermediate Similarity	NPC471724
0.8415	Intermediate Similarity	NPC143767
0.8415	Intermediate Similarity	NPC471722
0.8415	Intermediate Similarity	NPC131470
0.84	Intermediate Similarity	NPC138374
0.84	Intermediate Similarity	NPC291503
0.84	Intermediate Similarity	NPC477923

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 NPC322353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1995
0.2-0.3	4525
0.3-0.4	1796
0.4-0.5	305
0.5-0.6	166
0.6-0.7	165
0.7-0.8	45
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD7339	Approved
0.9167	High Similarity	NPD6942	Approved
0.8816	High Similarity	NPD7525	Registered
0.8533	High Similarity	NPD3701	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4748	Discontinued
0.8243	Intermediate Similarity	NPD4243	Approved
0.8205	Intermediate Similarity	NPD7645	Phase 2
0.8148	Intermediate Similarity	NPD4786	Approved
0.8095	Intermediate Similarity	NPD5328	Approved
0.8026	Intermediate Similarity	NPD6926	Approved
0.8026	Intermediate Similarity	NPD4784	Approved
0.8026	Intermediate Similarity	NPD6924	Approved
0.8026	Intermediate Similarity	NPD4785	Approved
0.8	Intermediate Similarity	NPD7150	Approved
0.8	Intermediate Similarity	NPD7151	Approved
0.8	Intermediate Similarity	NPD7152	Approved
0.7973	Intermediate Similarity	NPD6923	Approved
0.7973	Intermediate Similarity	NPD6922	Approved
0.7952	Intermediate Similarity	NPD3618	Phase 1
0.7907	Intermediate Similarity	NPD6079	Approved
0.7901	Intermediate Similarity	NPD3667	Approved
0.7867	Intermediate Similarity	NPD7144	Approved
0.7867	Intermediate Similarity	NPD7143	Approved
0.7821	Intermediate Similarity	NPD6933	Approved
0.7692	Intermediate Similarity	NPD4190	Phase 3
0.7692	Intermediate Similarity	NPD5275	Approved
0.7647	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4202	Approved
0.7531	Intermediate Similarity	NPD6929	Approved
0.7529	Intermediate Similarity	NPD5279	Phase 3
0.75	Intermediate Similarity	NPD3666	Approved
0.75	Intermediate Similarity	NPD3665	Phase 1
0.75	Intermediate Similarity	NPD3133	Approved
0.7468	Intermediate Similarity	NPD8264	Approved
0.7439	Intermediate Similarity	NPD6930	Phase 2
0.7439	Intermediate Similarity	NPD6931	Approved
0.7439	Intermediate Similarity	NPD7509	Discontinued
0.7363	Intermediate Similarity	NPD5222	Approved
0.7363	Intermediate Similarity	NPD4697	Phase 3
0.7363	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5221	Approved
0.7317	Intermediate Similarity	NPD4195	Approved
0.7284	Intermediate Similarity	NPD6932	Approved
0.7284	Intermediate Similarity	NPD6925	Approved
0.7284	Intermediate Similarity	NPD5776	Phase 2
0.7283	Intermediate Similarity	NPD4755	Approved
0.7283	Intermediate Similarity	NPD5173	Approved
0.7273	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7195	Intermediate Similarity	NPD7145	Approved
0.7176	Intermediate Similarity	NPD6695	Phase 3
0.7128	Intermediate Similarity	NPD4696	Approved
0.7128	Intermediate Similarity	NPD5286	Approved
0.7128	Intermediate Similarity	NPD5285	Approved
0.7128	Intermediate Similarity	NPD4700	Approved
0.7111	Intermediate Similarity	NPD7515	Phase 2
0.7108	Intermediate Similarity	NPD6683	Phase 2
0.7093	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3668	Phase 3
0.7079	Intermediate Similarity	NPD4753	Phase 2
0.7059	Intermediate Similarity	NPD4221	Approved
0.7059	Intermediate Similarity	NPD4223	Phase 3
0.7053	Intermediate Similarity	NPD5223	Approved
0.7024	Intermediate Similarity	NPD7514	Phase 3
0.7021	Intermediate Similarity	NPD7638	Approved
0.7021	Intermediate Similarity	NPD5290	Discontinued
0.7011	Intermediate Similarity	NPD5329	Approved
0.7011	Intermediate Similarity	NPD6893	Approved
0.6988	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4633	Approved
0.6979	Remote Similarity	NPD5224	Approved
0.6979	Remote Similarity	NPD5211	Phase 2
0.6979	Remote Similarity	NPD5225	Approved
0.6979	Remote Similarity	NPD5226	Approved
0.6977	Remote Similarity	NPD4788	Approved
0.6962	Remote Similarity	NPD4787	Phase 1
0.6947	Remote Similarity	NPD7639	Approved
0.6947	Remote Similarity	NPD7640	Approved
0.6941	Remote Similarity	NPD6902	Approved
0.6941	Remote Similarity	NPD4139	Approved
0.6941	Remote Similarity	NPD4692	Approved
0.6939	Remote Similarity	NPD6675	Approved
0.6939	Remote Similarity	NPD6402	Approved
0.6939	Remote Similarity	NPD7128	Approved
0.6939	Remote Similarity	NPD5739	Approved
0.6932	Remote Similarity	NPD4694	Approved
0.6932	Remote Similarity	NPD5280	Approved
0.6932	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD8034	Phase 2
0.6907	Remote Similarity	NPD4754	Approved
0.6907	Remote Similarity	NPD5175	Approved
0.6907	Remote Similarity	NPD5174	Approved
0.6897	Remote Similarity	NPD4197	Approved
0.6875	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7524	Approved
0.6854	Remote Similarity	NPD7750	Discontinued
0.6837	Remote Similarity	NPD5141	Approved
0.6824	Remote Similarity	NPD7332	Phase 2
0.68	Remote Similarity	NPD6899	Approved
0.68	Remote Similarity	NPD7320	Approved
0.68	Remote Similarity	NPD6881	Approved
0.6786	Remote Similarity	NPD3617	Approved
0.6774	Remote Similarity	NPD7748	Approved
0.6768	Remote Similarity	NPD4768	Approved
0.6768	Remote Similarity	NPD4767	Approved
0.6747	Remote Similarity	NPD6117	Approved
0.6744	Remote Similarity	NPD6898	Phase 1
0.6742	Remote Similarity	NPD6684	Approved
0.6742	Remote Similarity	NPD5205	Approved
0.6742	Remote Similarity	NPD4689	Approved
0.6742	Remote Similarity	NPD4690	Approved
0.6742	Remote Similarity	NPD7334	Approved
0.6742	Remote Similarity	NPD6409	Approved
0.6742	Remote Similarity	NPD7146	Approved
0.6742	Remote Similarity	NPD5330	Approved
0.6742	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4693	Phase 3
0.6742	Remote Similarity	NPD4138	Approved
0.6742	Remote Similarity	NPD4688	Approved
0.6742	Remote Similarity	NPD7521	Approved
0.6737	Remote Similarity	NPD6084	Phase 2
0.6737	Remote Similarity	NPD6083	Phase 2
0.6733	Remote Similarity	NPD6373	Approved
0.6733	Remote Similarity	NPD6372	Approved
0.6707	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6051	Approved
0.6702	Remote Similarity	NPD5210	Approved
0.6702	Remote Similarity	NPD5695	Phase 3
0.6702	Remote Similarity	NPD4629	Approved
0.67	Remote Similarity	NPD5701	Approved
0.67	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6634	Remote Similarity	NPD5128	Approved
0.6634	Remote Similarity	NPD4729	Approved
0.6634	Remote Similarity	NPD4730	Approved
0.6634	Remote Similarity	NPD6011	Approved
0.6634	Remote Similarity	NPD5168	Approved
0.6625	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6847	Approved
0.6602	Remote Similarity	NPD6650	Approved
0.6602	Remote Similarity	NPD6617	Approved
0.6602	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6869	Approved
0.6602	Remote Similarity	NPD8130	Phase 1
0.6602	Remote Similarity	NPD6649	Approved
0.6593	Remote Similarity	NPD6672	Approved
0.6593	Remote Similarity	NPD4722	Approved
0.6593	Remote Similarity	NPD6903	Approved
0.6593	Remote Similarity	NPD5737	Approved
0.6593	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4723	Approved
0.6588	Remote Similarity	NPD6697	Approved
0.6588	Remote Similarity	NPD6115	Approved
0.6588	Remote Similarity	NPD6114	Approved
0.6588	Remote Similarity	NPD6118	Approved
0.6579	Remote Similarity	NPD368	Approved
0.6569	Remote Similarity	NPD6012	Approved
0.6569	Remote Similarity	NPD6014	Approved
0.6569	Remote Similarity	NPD6013	Approved
0.6562	Remote Similarity	NPD7902	Approved
0.6559	Remote Similarity	NPD5284	Approved
0.6559	Remote Similarity	NPD5281	Approved
0.6559	Remote Similarity	NPD7087	Discontinued
0.6538	Remote Similarity	NPD8297	Approved
0.6538	Remote Similarity	NPD6882	Approved
0.6531	Remote Similarity	NPD4159	Approved
0.6506	Remote Similarity	NPD5733	Approved
0.6505	Remote Similarity	NPD5249	Phase 3
0.6505	Remote Similarity	NPD5169	Approved
0.6505	Remote Similarity	NPD5248	Approved
0.6505	Remote Similarity	NPD5247	Approved
0.6505	Remote Similarity	NPD5250	Approved
0.6505	Remote Similarity	NPD5251	Approved
0.6505	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4634	Approved
0.6505	Remote Similarity	NPD5135	Approved
0.6465	Remote Similarity	NPD7632	Discontinued
0.6452	Remote Similarity	NPD4096	Approved
0.6442	Remote Similarity	NPD5127	Approved
0.6442	Remote Similarity	NPD5215	Approved
0.6442	Remote Similarity	NPD5216	Approved
0.6442	Remote Similarity	NPD5217	Approved
0.6438	Remote Similarity	NPD342	Phase 1
0.6429	Remote Similarity	NPD3703	Phase 2
0.6383	Remote Similarity	NPD6411	Approved
0.6374	Remote Similarity	NPD6098	Approved
0.6355	Remote Similarity	NPD6868	Approved
0.6354	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4747	Approved
0.6341	Remote Similarity	NPD4789	Approved
0.6341	Remote Similarity	NPD4244	Approved
0.6341	Remote Similarity	NPD4245	Approved
0.6329	Remote Similarity	NPD3171	Clinical (unspecified phase)

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