NPASS Compound

Structure

CID264005 OpenBabel06191716062D 34 38 0 0 1 0 0 0 0 0999 V2000 -5.7237 -0.3466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1878 -0.9357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0245 -1.9152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4530 -1.4238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8719 1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6458 -0.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8227 -1.4258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1145 1.4238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6450 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6463 -2.8496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8234 -2.3752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8223 0.4754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2928 1.8992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8235 1.4247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6467 1.8996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9601 -0.5712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7857 -0.1978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1143 0.4740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6461 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6452 -0.9499 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4687 -2.3742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4693 0.4745 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4699 2.3740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8229 -1.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4681 -1.4243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8232 0.4749 0.0000 C 0 0 1 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 -2.4696 1.4242 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9449 -0.5706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3219 -2.8662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5667 2.6678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1759 3.0093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 20 1 0 0 0 0 8 22 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 27 1 0 0 0 0 17 31 1 0 0 0 0 19 18 1 6 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 20 28 1 6 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 26 1 1 0 0 0 22 29 1 0 0 0 0 23 27 1 1 0 0 0 23 32 1 0 0 0 0 24 30 1 1 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	4.415
LogD:	4.3
LogS:	-4.009
# Rotatable Bonds:	3
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	4.839
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.402
MDCK Permeability:	2.8285374355618842e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.866
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	88.29267883300781%
Volume Distribution (VD):	0.572
Pgp-substrate:	3.4601330757141113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.341
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.123
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.4
CYP3A4-inhibitor:	0.295
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	2.515
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.268
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.793
Carcinogencity:	0.016
Eye Corrosion:	0.129
Eye Irritation:	0.407
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC264005

Natural Product ID:	NPC264005
*Common Name:**	23-Hydroxy Betulic Acid
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-hydroxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms:	23-Hydroxy Betulic Acid; 23-Hydroxybetulinic Acid; 23-Hydroxybetulinicacid
Standard InCHIKey:	HXWLKAXCQLXHML-WGOZWDAUSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18(2)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-26(3)12-11-23(32)27(4,17-31)21(26)10-13-29(22,28)6/h19-24,31-32H,1,7-17H2,2-6H3,(H,33,34)/t19-,20+,21+,22+,23-,24+,26-,27-,28+,29+,30-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O)[C@@H]12)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251308
PubChem CID:	21672692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[10514313]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[11575962]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	roots	Whitessence Srl, Viterbo, Italy	2005-OCT	PMID[21954959]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21954959]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	DingXi, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	LanZhou, GanSu, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	10 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	20 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	30 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	40 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	50 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	60 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Seeds	Yangling, Shaanxi, China	Maturation	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	70 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	80 days after pollination	PMID[33131958]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	Fruits	Yangling, Shaanxi, China	90 days after pollination	PMID[33131958]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18782.1	Pulsatilla cernua var. koreana	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18782.1	Pulsatilla cernua var. koreana	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15265	Paeonia rockii	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1373	Pulsatilla chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	41
MIC	6
Others	18

Activity Type	# Activity
Cell Line	35
CELL-LINE	1
Individual Protein	6
NON-MOLECULAR	10
Organism	10
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	87600.0	nM	PMID[476708]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	97320.0	nM	PMID[476708]
NPT319	Cell Line	B16	Mus musculus	IC50	=	83040.0	nM	PMID[476708]
NPT76	Cell Line	C6	Rattus norvegicus	IC50	=	99480.0	nM	PMID[476708]
NPT1357	Cell Line	H22	Mus musculus	Activity	=	1.42	g	PMID[476708]
NPT1357	Cell Line	H22	Mus musculus	Inhibition	=	10.1	%	PMID[476708]
NPT319	Cell Line	B16	Mus musculus	Activity	=	1.76	g	PMID[476708]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	13.3	%	PMID[476708]
NPT2681	Individual Protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	16000.0	nM	PMID[476709]
NPT2681	Individual Protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	103000.0	nM	PMID[476710]
NPT319	Cell Line	B16	Mus musculus	IC50	=	18680.0	nM	PMID[476711]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	41410.0	nM	PMID[476711]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	41990.0	nM	PMID[476711]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	46220.0	nM	PMID[476711]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	46610.0	nM	PMID[476711]
NPT2681	Individual Protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	16000.0	nM	PMID[476712]
NPT2681	Individual Protein	Glycogen phosphorylase, muscle form	Oryctolagus cuniculus	IC50	=	15848.93	nM	PMID[476712]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	50000.0	nM	PMID[476713]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	52390.0	nM	PMID[476715]
NPT319	Cell Line	B16	Mus musculus	IC50	=	29870.0	nM	PMID[476715]
NPT1357	Cell Line	H22	Mus musculus	Inhibition	=	27.8	%	PMID[476715]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	32.4	%	PMID[476715]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	52390.0	nM	PMID[476716]
NPT319	Cell Line	B16	Mus musculus	IC50	=	29870.0	nM	PMID[476716]
NPT1357	Cell Line	H22	Mus musculus	Inhibition	=	27.8	%	PMID[476716]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	32.4	%	PMID[476716]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	52390.0	nM	PMID[476717]
NPT319	Cell Line	B16	Mus musculus	IC50	=	29870.0	nM	PMID[476717]
NPT1357	Cell Line	H22	Mus musculus	Inhibition	=	27.8	%	PMID[476717]
NPT319	Cell Line	B16	Mus musculus	Inhibition	=	32.4	%	PMID[476717]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	=	24460.0	nM	PMID[476718]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	20830.0	nM	PMID[476718]
NPT169	Cell Line	B16-F10	Mus musculus	Activity	=	10.57	%	PMID[476718]
NPT169	Cell Line	B16-F10	Mus musculus	Activity	=	22.85	%	PMID[476718]
NPT169	Cell Line	B16-F10	Mus musculus	Activity	=	42.87	%	PMID[476718]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	71840.0	nM	PMID[476719]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	74980.0	nM	PMID[476719]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	76300.0	nM	PMID[476719]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	79120.0	nM	PMID[476719]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	1900.0	nM	PMID[476720]
NPT166	Individual Protein	Acyl coenzyme A:cholesterol acyltransferase	Homo sapiens	IC50	=	100.0	nM	PMID[476720]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	104540.0	nM	PMID[476708]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	MIC	>	128.0	ug.mL-1	PMID[476714]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128.0	ug.mL-1	PMID[476714]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[476714]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	MIC	=	8.0	ug.mL-1	PMID[476714]
NPT1101	Organism	Staphylococcus aureus subsp. aureus RN4220	Staphylococcus aureus subsp. aureus RN4220	MIC	=	16.0	ug.mL-1	PMID[476714]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[476714]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	43400.0	nM	PMID[476715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39670.0	nM	PMID[476715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45150.0	nM	PMID[476715]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45150.0	nM	PMID[476716]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39670.0	nM	PMID[476716]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	43400.0	nM	PMID[476716]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	26.1	g	PMID[476716]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	26.7	g	PMID[476716]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	45150.0	nM	PMID[476717]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39670.0	nM	PMID[476717]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	43400.0	nM	PMID[476717]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	26.1	g	PMID[476717]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	26.7	g	PMID[476717]
NPT2	Others	Unspecified		IC50	=	31490.0	nM	PMID[476718]
NPT21742	CELL-LINE	L02	Homo sapiens	IC50	=	79150.0	nM	PMID[476719]
NPT2	Others	Unspecified		IC50	=	70330.0	nM	PMID[476719]
NPT2	Others	Unspecified		Ratio IC50	=	30.0	n.a.	PMID[476720]

☑ 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 NPC264005 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	194
0.1-0.2	1620
0.2-0.3	6458
0.3-0.4	15766
0.4-0.5	6265
0.5-0.6	4781
0.6-0.7	4546
0.7-0.8	2534
0.8-0.85	393
0.85-0.9	91
0.9-0.95	29
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC269360
0.9877	High Similarity	NPC2783
0.9759	High Similarity	NPC213832
0.9759	High Similarity	NPC57954
0.9756	High Similarity	NPC33768
0.9753	High Similarity	NPC264317
0.9753	High Similarity	NPC294438
0.9639	High Similarity	NPC471900
0.9639	High Similarity	NPC474719
0.9639	High Similarity	NPC16377
0.9634	High Similarity	NPC12774
0.9524	High Similarity	NPC220498
0.9419	High Similarity	NPC473690
0.9419	High Similarity	NPC287118
0.9419	High Similarity	NPC471902
0.9412	High Similarity	NPC169933
0.9405	High Similarity	NPC4309
0.931	High Similarity	NPC277399
0.9302	High Similarity	NPC471901
0.9302	High Similarity	NPC475416
0.9294	High Similarity	NPC247312
0.9294	High Similarity	NPC271974
0.9268	High Similarity	NPC472743
0.9268	High Similarity	NPC475726
0.9195	High Similarity	NPC224060
0.9195	High Similarity	NPC244356
0.9195	High Similarity	NPC291373
0.9176	High Similarity	NPC146937
0.9157	High Similarity	NPC474482
0.9157	High Similarity	NPC74595
0.9157	High Similarity	NPC475745
0.9157	High Similarity	NPC264665
0.908	High Similarity	NPC160506
0.907	High Similarity	NPC475921
0.907	High Similarity	NPC474704
0.9048	High Similarity	NPC292553
0.9048	High Similarity	NPC201655
0.9048	High Similarity	NPC98270
0.9036	High Similarity	NPC471037
0.8941	High Similarity	NPC472738
0.8941	High Similarity	NPC187545
0.8941	High Similarity	NPC98236
0.8941	High Similarity	NPC80590
0.8941	High Similarity	NPC269396
0.8929	High Similarity	NPC475509
0.8929	High Similarity	NPC474233
0.8876	High Similarity	NPC303863
0.8851	High Similarity	NPC61543
0.8851	High Similarity	NPC59263
0.8851	High Similarity	NPC234346
0.8851	High Similarity	NPC127689
0.8851	High Similarity	NPC225585
0.8851	High Similarity	NPC263393
0.8851	High Similarity	NPC130520
0.8851	High Similarity	NPC270768
0.8851	High Similarity	NPC121798
0.8851	High Similarity	NPC293048
0.8837	High Similarity	NPC142361
0.8837	High Similarity	NPC4643
0.8837	High Similarity	NPC57469
0.8837	High Similarity	NPC134197
0.8837	High Similarity	NPC474684
0.881	High Similarity	NPC245866
0.881	High Similarity	NPC5280
0.878	High Similarity	NPC201459
0.878	High Similarity	NPC192744
0.8778	High Similarity	NPC288906
0.8778	High Similarity	NPC205173
0.8778	High Similarity	NPC266431
0.8778	High Similarity	NPC263135
0.8765	High Similarity	NPC298168
0.8765	High Similarity	NPC143133
0.8765	High Similarity	NPC474433
0.8765	High Similarity	NPC68828
0.8764	High Similarity	NPC294263
0.8764	High Similarity	NPC475061
0.875	High Similarity	NPC126369
0.875	High Similarity	NPC111110
0.875	High Similarity	NPC130278
0.875	High Similarity	NPC470589
0.8736	High Similarity	NPC211162
0.8736	High Similarity	NPC183374
0.8736	High Similarity	NPC472739
0.8736	High Similarity	NPC52169
0.8736	High Similarity	NPC242864
0.8736	High Similarity	NPC182797
0.8721	High Similarity	NPC168231
0.8721	High Similarity	NPC70661
0.8721	High Similarity	NPC28252
0.8721	High Similarity	NPC55309
0.8681	High Similarity	NPC234564
0.8652	High Similarity	NPC966
0.8652	High Similarity	NPC288833
0.8652	High Similarity	NPC228784
0.8652	High Similarity	NPC189520
0.8652	High Similarity	NPC324341
0.8652	High Similarity	NPC155120
0.8652	High Similarity	NPC282616
0.8642	High Similarity	NPC78067
0.8642	High Similarity	NPC246445
0.8642	High Similarity	NPC278091
0.8642	High Similarity	NPC4209
0.8642	High Similarity	NPC93662
0.8636	High Similarity	NPC274330
0.8636	High Similarity	NPC143232
0.8636	High Similarity	NPC25906
0.8636	High Similarity	NPC198664
0.8636	High Similarity	NPC64872
0.8636	High Similarity	NPC290972
0.8621	High Similarity	NPC293564
0.8621	High Similarity	NPC242468
0.8621	High Similarity	NPC18064
0.8621	High Similarity	NPC307426
0.8621	High Similarity	NPC102683
0.8621	High Similarity	NPC68160
0.8621	High Similarity	NPC88716
0.8621	High Similarity	NPC130577
0.8621	High Similarity	NPC98442
0.8621	High Similarity	NPC51700
0.8621	High Similarity	NPC187376
0.8621	High Similarity	NPC142415
0.8621	High Similarity	NPC159046
0.8621	High Similarity	NPC171203
0.8621	High Similarity	NPC233836
0.8605	High Similarity	NPC76518
0.8587	High Similarity	NPC253586
0.8571	High Similarity	NPC210214
0.8571	High Similarity	NPC474484
0.8571	High Similarity	NPC279974
0.8571	High Similarity	NPC103754
0.8556	High Similarity	NPC470376
0.8556	High Similarity	NPC86368
0.8556	High Similarity	NPC470375
0.8556	High Similarity	NPC229281
0.8539	High Similarity	NPC477872
0.8539	High Similarity	NPC471896
0.8539	High Similarity	NPC227467
0.8539	High Similarity	NPC7260
0.8539	High Similarity	NPC86372
0.8539	High Similarity	NPC120968
0.8539	High Similarity	NPC273621
0.8539	High Similarity	NPC46758
0.8539	High Similarity	NPC18872
0.8539	High Similarity	NPC469400
0.8539	High Similarity	NPC210037
0.8539	High Similarity	NPC172361
0.8539	High Similarity	NPC291028
0.8539	High Similarity	NPC290614
0.8537	High Similarity	NPC66105
0.8537	High Similarity	NPC207010
0.8537	High Similarity	NPC317913
0.8523	High Similarity	NPC470629
0.8523	High Similarity	NPC181225
0.8523	High Similarity	NPC290690
0.8523	High Similarity	NPC473242
0.8523	High Similarity	NPC17733
0.8523	High Similarity	NPC246708
0.8523	High Similarity	NPC474512
0.8523	High Similarity	NPC40552
0.8519	High Similarity	NPC240235
0.8519	High Similarity	NPC212879
0.8519	High Similarity	NPC212733
0.8519	High Similarity	NPC104387
0.8519	High Similarity	NPC231256
0.8519	High Similarity	NPC178383
0.8506	High Similarity	NPC155011
0.8506	High Similarity	NPC72638
0.8495	Intermediate Similarity	NPC119036
0.8488	Intermediate Similarity	NPC299963
0.8488	Intermediate Similarity	NPC263974
0.8478	Intermediate Similarity	NPC327788
0.8471	Intermediate Similarity	NPC289486
0.8471	Intermediate Similarity	NPC30583
0.8471	Intermediate Similarity	NPC61107
0.8471	Intermediate Similarity	NPC170985
0.8462	Intermediate Similarity	NPC299996
0.8462	Intermediate Similarity	NPC20235
0.8462	Intermediate Similarity	NPC88116
0.8462	Intermediate Similarity	NPC231063
0.8462	Intermediate Similarity	NPC145667
0.8462	Intermediate Similarity	NPC282395
0.8462	Intermediate Similarity	NPC114159
0.8462	Intermediate Similarity	NPC32407
0.8462	Intermediate Similarity	NPC47853
0.8462	Intermediate Similarity	NPC191412
0.8462	Intermediate Similarity	NPC159365
0.8462	Intermediate Similarity	NPC222047
0.8462	Intermediate Similarity	NPC263548
0.8462	Intermediate Similarity	NPC6818
0.8452	Intermediate Similarity	NPC261616
0.8452	Intermediate Similarity	NPC164999
0.8452	Intermediate Similarity	NPC206735
0.8452	Intermediate Similarity	NPC304194
0.8444	Intermediate Similarity	NPC212301
0.8444	Intermediate Similarity	NPC211403
0.8444	Intermediate Similarity	NPC6255
0.8444	Intermediate Similarity	NPC84319
0.8444	Intermediate Similarity	NPC145067
0.8444	Intermediate Similarity	NPC187722
0.8444	Intermediate Similarity	NPC105189

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 NPC264005 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	2031
0.2-0.3	4115
0.3-0.4	1911
0.4-0.5	478
0.5-0.6	147
0.6-0.7	180
0.7-0.8	105
0.8-0.85	7
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9753	High Similarity	NPD7520	Clinical (unspecified phase)
0.908	High Similarity	NPD8034	Phase 2
0.908	High Similarity	NPD8035	Phase 2
0.8642	High Similarity	NPD6117	Approved
0.8537	High Similarity	NPD6116	Phase 1
0.8444	Intermediate Similarity	NPD7515	Phase 2
0.8434	Intermediate Similarity	NPD6697	Approved
0.8434	Intermediate Similarity	NPD6118	Approved
0.8434	Intermediate Similarity	NPD6115	Approved
0.8434	Intermediate Similarity	NPD6114	Approved
0.8395	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD4786	Approved
0.8065	Intermediate Similarity	NPD7748	Approved
0.8022	Intermediate Similarity	NPD5328	Approved
0.7957	Intermediate Similarity	NPD6399	Phase 3
0.7955	Intermediate Similarity	NPD4788	Approved
0.7927	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3618	Phase 1
0.7849	Intermediate Similarity	NPD6079	Approved
0.7841	Intermediate Similarity	NPD3667	Approved
0.7816	Intermediate Similarity	NPD7525	Registered
0.7812	Intermediate Similarity	NPD7902	Approved
0.78	Intermediate Similarity	NPD5739	Approved
0.78	Intermediate Similarity	NPD7128	Approved
0.78	Intermediate Similarity	NPD6675	Approved
0.78	Intermediate Similarity	NPD6402	Approved
0.7732	Intermediate Similarity	NPD7638	Approved
0.7683	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD7640	Approved
0.7653	Intermediate Similarity	NPD7639	Approved
0.7647	Intermediate Similarity	NPD7320	Approved
0.7647	Intermediate Similarity	NPD6899	Approved
0.7647	Intermediate Similarity	NPD6881	Approved
0.7629	Intermediate Similarity	NPD6084	Phase 2
0.7629	Intermediate Similarity	NPD6083	Phase 2
0.7629	Intermediate Similarity	NPD4755	Approved
0.7579	Intermediate Similarity	NPD4202	Approved
0.7573	Intermediate Similarity	NPD6373	Approved
0.7573	Intermediate Similarity	NPD6372	Approved
0.7549	Intermediate Similarity	NPD5701	Approved
0.7549	Intermediate Similarity	NPD5697	Approved
0.7527	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD4697	Phase 3
0.7526	Intermediate Similarity	NPD5221	Approved
0.7526	Intermediate Similarity	NPD5222	Approved
0.7526	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6081	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7645	Phase 2
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.7475	Intermediate Similarity	NPD5285	Approved
0.7475	Intermediate Similarity	NPD5286	Approved
0.7475	Intermediate Similarity	NPD4700	Approved
0.7475	Intermediate Similarity	NPD4696	Approved
0.7473	Intermediate Similarity	NPD3666	Approved
0.7473	Intermediate Similarity	NPD3665	Phase 1
0.7473	Intermediate Similarity	NPD3133	Approved
0.7449	Intermediate Similarity	NPD5173	Approved
0.7447	Intermediate Similarity	NPD4753	Phase 2
0.7442	Intermediate Similarity	NPD3703	Phase 2
0.7429	Intermediate Similarity	NPD6869	Approved
0.7429	Intermediate Similarity	NPD6650	Approved
0.7429	Intermediate Similarity	NPD8130	Phase 1
0.7429	Intermediate Similarity	NPD6649	Approved
0.7429	Intermediate Similarity	NPD6617	Approved
0.7429	Intermediate Similarity	NPD6847	Approved
0.7404	Intermediate Similarity	NPD6012	Approved
0.7404	Intermediate Similarity	NPD6013	Approved
0.7404	Intermediate Similarity	NPD6014	Approved
0.7381	Intermediate Similarity	NPD4244	Approved
0.7381	Intermediate Similarity	NPD4245	Approved
0.7381	Intermediate Similarity	NPD4789	Approved
0.7358	Intermediate Similarity	NPD8297	Approved
0.7358	Intermediate Similarity	NPD6882	Approved
0.7349	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5360	Phase 3
0.734	Intermediate Similarity	NPD6672	Approved
0.734	Intermediate Similarity	NPD5737	Approved
0.7327	Intermediate Similarity	NPD5224	Approved
0.7327	Intermediate Similarity	NPD5211	Phase 2
0.7327	Intermediate Similarity	NPD5225	Approved
0.7327	Intermediate Similarity	NPD5226	Approved
0.7327	Intermediate Similarity	NPD4633	Approved
0.7317	Intermediate Similarity	NPD4224	Phase 2
0.7312	Intermediate Similarity	NPD6684	Approved
0.7312	Intermediate Similarity	NPD5330	Approved
0.7312	Intermediate Similarity	NPD7334	Approved
0.7312	Intermediate Similarity	NPD7146	Approved
0.7312	Intermediate Similarity	NPD7521	Approved
0.7312	Intermediate Similarity	NPD6409	Approved
0.7308	Intermediate Similarity	NPD6011	Approved
0.729	Intermediate Similarity	NPD8133	Approved
0.7283	Intermediate Similarity	NPD3668	Phase 3
0.7264	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3698	Phase 2
0.7262	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5175	Approved
0.7255	Intermediate Similarity	NPD5174	Approved
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7245	Intermediate Similarity	NPD5695	Phase 3
0.7241	Intermediate Similarity	NPD7339	Approved
0.7241	Intermediate Similarity	NPD6942	Approved
0.7228	Intermediate Similarity	NPD5223	Approved
0.72	Intermediate Similarity	NPD5696	Approved
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5141	Approved
0.7158	Intermediate Similarity	NPD6903	Approved
0.7157	Intermediate Similarity	NPD7632	Discontinued
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7115	Intermediate Similarity	NPD4768	Approved
0.7115	Intermediate Similarity	NPD4767	Approved
0.7093	Intermediate Similarity	NPD5777	Approved
0.7087	Intermediate Similarity	NPD4754	Approved
0.7071	Intermediate Similarity	NPD4629	Approved
0.7071	Intermediate Similarity	NPD5210	Approved
0.7071	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4221	Approved
0.7065	Intermediate Similarity	NPD4223	Phase 3
0.7045	Intermediate Similarity	NPD3702	Approved
0.7021	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD3671	Phase 1
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD6868	Approved
0.6981	Remote Similarity	NPD4730	Approved
0.6981	Remote Similarity	NPD4729	Approved
0.6981	Remote Similarity	NPD5128	Approved
0.6972	Remote Similarity	NPD4632	Approved
0.6966	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7101	Approved
0.6964	Remote Similarity	NPD7100	Approved
0.6947	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6098	Approved
0.6939	Remote Similarity	NPD6411	Approved
0.6939	Remote Similarity	NPD5281	Approved
0.6939	Remote Similarity	NPD5284	Approved
0.6915	Remote Similarity	NPD4197	Approved
0.6907	Remote Similarity	NPD6904	Approved
0.6907	Remote Similarity	NPD6673	Approved
0.6907	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6080	Approved
0.6897	Remote Similarity	NPD7507	Approved
0.6897	Remote Similarity	NPD4758	Discontinued
0.6887	Remote Similarity	NPD6412	Phase 2
0.6875	Remote Similarity	NPD6335	Approved
0.6852	Remote Similarity	NPD5247	Approved
0.6852	Remote Similarity	NPD5251	Approved
0.6852	Remote Similarity	NPD5248	Approved
0.6852	Remote Similarity	NPD5249	Phase 3
0.6852	Remote Similarity	NPD5250	Approved
0.6852	Remote Similarity	NPD4634	Approved
0.6842	Remote Similarity	NPD6909	Approved
0.6842	Remote Similarity	NPD6908	Approved
0.6822	Remote Similarity	NPD5168	Approved
0.6813	Remote Similarity	NPD5364	Discontinued
0.6813	Remote Similarity	NPD3617	Approved
0.6796	Remote Similarity	NPD8418	Phase 2
0.6792	Remote Similarity	NPD6008	Approved
0.6789	Remote Similarity	NPD5216	Approved
0.6789	Remote Similarity	NPD5217	Approved
0.6789	Remote Similarity	NPD5215	Approved
0.6786	Remote Similarity	NPD6009	Approved
0.6786	Remote Similarity	NPD6317	Approved
0.678	Remote Similarity	NPD7736	Approved
0.6771	Remote Similarity	NPD4138	Approved
0.6771	Remote Similarity	NPD4688	Approved
0.6771	Remote Similarity	NPD4690	Approved
0.6771	Remote Similarity	NPD5205	Approved
0.6771	Remote Similarity	NPD4693	Phase 3
0.6771	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD7637	Suspended
0.6759	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6319	Approved
0.6742	Remote Similarity	NPD6926	Approved
0.6742	Remote Similarity	NPD6924	Approved
0.6735	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6101	Approved
0.6726	Remote Similarity	NPD6313	Approved
0.6726	Remote Similarity	NPD6314	Approved
0.6723	Remote Similarity	NPD7319	Approved
0.6701	Remote Similarity	NPD3573	Approved
0.6699	Remote Similarity	NPD4225	Approved
0.6697	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5135	Approved
0.6697	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6637	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5127	Approved
0.6634	Remote Similarity	NPD6001	Approved
0.6633	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD5362	Discontinued
0.661	Remote Similarity	NPD6616	Approved
0.6609	Remote Similarity	NPD6059	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