NPASS Compound

Structure

CID237549 OpenBabel06191716042D 49 53 0 0 1 0 0 0 0 0999 V2000 -2.4920 -1.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0999 2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0592 2.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0407 2.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7219 -2.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7980 -1.2182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 -4.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7999 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 -3.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9499 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7999 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 -4.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0999 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9499 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 2.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2499 2.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 -3.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0999 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 -1.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7000 0.9815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8500 -0.4907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4000 0.9815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5500 -0.4907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7000 -2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 -0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 -1.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7000 2.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 2.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2499 -0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 -3.4352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -2.9444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 1.4722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2499 1.4722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -1.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 -1.4722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 35 1 0 0 0 0 5 35 1 0 0 0 0 8 36 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 23 2 0 0 0 0 16 23 1 0 0 0 0 17 24 2 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 36 1 0 0 0 0 21 39 2 0 0 0 0 21 46 1 0 0 0 0 22 40 2 0 0 0 0 22 47 1 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 25 29 1 0 0 0 0 25 48 1 6 0 0 0 26 35 1 0 0 0 0 26 37 1 1 0 0 0 27 38 1 6 0 0 0 27 46 1 0 0 0 0 28 30 1 0 0 0 0 28 31 1 0 0 0 0 28 41 1 6 0 0 0 29 37 1 1 0 0 0 29 38 1 0 0 0 0 30 35 1 0 0 0 0 30 47 1 6 0 0 0 31 37 1 6 0 0 0 31 49 1 0 0 0 0 32 42 2 0 0 0 0 32 48 1 0 0 0 0 33 43 2 0 0 0 0 33 49 1 0 0 0 0 34 36 1 0 0 0 0 34 38 1 0 0 0 0 34 44 2 0 0 0 0 36 6 1 1 0 0 0 37 7 1 1 0 0 0 38 45 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	676.29
Volume:	688.077
LogP:	4.583
LogD:	2.701
LogS:	-4.606
# Rotatable Bonds:	11
TPSA:	162.73
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	5.172
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.157
MDCK Permeability:	2.4495604520780034e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.548

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.42
Plasma Protein Binding (PPB):	96.41350555419922%
Volume Distribution (VD):	1.687
Pgp-substrate:	7.066704273223877%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.054
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.745
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	3.312
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.349
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.159
Carcinogencity:	0.079
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC237549

Natural Product ID:	NPC237549
*Common Name:**	Orthosiphol B
IUPAC Name:	[(2R,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-7,10-diacetyloxy-5-benzoyloxy-2-ethenyl-6,10a-dihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
Synonyms:
Standard InCHIKey:	BXKNTIMTKVZYDP-OFUWLHILSA-N
Standard InCHI:	InChI=1S/C38H44O11/c1-8-36(6)20-25(48-32(42)23-15-11-9-12-16-23)29-37(7)26(19-27(46-21(2)39)38(29,45)34(36)44)35(4,5)30(47-22(3)40)28(41)31(37)49-33(43)24-17-13-10-14-18-24/h8-18,25-31,41,45H,1,19-20H2,2-7H3/t25-,26+,27-,28+,29-,30-,31+,36+,37+,38+/m1/s1
SMILES:	C=C[C@@]1(C)C[C@@H](OC(=O)c2ccccc2)[C@H]2[C@@](C1=O)(O)[C@H](OC(=O)C)C[C@@H]1[C@]2(C)[C@@H](OC(=O)c2ccccc2)[C@@H](O)[C@H](C1(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509129
PubChem CID:	15385859
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654417]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374950]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[12467611]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	aerial parts	Bangdung, Indonesia	2000-Aug	PMID[12608860]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15104497]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19691312]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26473275]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28898076]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1638	Ulmus laciniata	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2499	Celmisia petriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8981	Senecio integerrimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2257	Oceanapia phillipensis	Species	Phloeodictyidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5890	Astragalus inopinatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14797	Orthosiphon aristatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1408	Cirsium helenioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO592	Chroogomphus rutilus	Species	Gomphidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5511	Populus tremula	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14887	Handroanthus guayacan	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23141	Angelica ursina	Species	Apiaceae	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
ED50	2
IC50	1

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	57.9	ug ml-1	PMID[554066]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	28.1	ug ml-1	PMID[554066]
NPT20763	CELL-LINE	J774.1	Mus musculus	IC50	=	20500.0	nM	PMID[554067]

☑ 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 NPC237549 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	348
0.1-0.2	1156
0.2-0.3	2531
0.3-0.4	4838
0.4-0.5	9196
0.5-0.6	10390
0.6-0.7	10412
0.7-0.8	3338
0.8-0.85	256
0.85-0.9	178
0.9-0.95	25
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC257213
1.0	High Similarity	NPC249471
1.0	High Similarity	NPC265395
1.0	High Similarity	NPC1173
1.0	High Similarity	NPC256142
1.0	High Similarity	NPC472005
1.0	High Similarity	NPC472030
1.0	High Similarity	NPC473414
1.0	High Similarity	NPC304876
1.0	High Similarity	NPC242262
1.0	High Similarity	NPC158333
1.0	High Similarity	NPC472022
0.9931	High Similarity	NPC114410
0.9931	High Similarity	NPC112523
0.9931	High Similarity	NPC26033
0.9931	High Similarity	NPC228204
0.9861	High Similarity	NPC77719
0.9795	High Similarity	NPC469771
0.979	High Similarity	NPC7095
0.972	High Similarity	NPC60509
0.972	High Similarity	NPC81698
0.972	High Similarity	NPC250046
0.9653	High Similarity	NPC198455
0.9653	High Similarity	NPC161239
0.9653	High Similarity	NPC112216
0.9653	High Similarity	NPC165260
0.9595	High Similarity	NPC471102
0.9592	High Similarity	NPC106895
0.9524	High Similarity	NPC472549
0.9524	High Similarity	NPC282239
0.9521	High Similarity	NPC477905
0.951	High Similarity	NPC127857
0.9459	High Similarity	NPC217091
0.9396	High Similarity	NPC472393
0.9388	High Similarity	NPC472548
0.932	High Similarity	NPC51602
0.932	High Similarity	NPC470153
0.932	High Similarity	NPC306799
0.932	High Similarity	NPC471103
0.932	High Similarity	NPC101043
0.9262	High Similarity	NPC473670
0.9262	High Similarity	NPC21410
0.9252	High Similarity	NPC473214
0.9252	High Similarity	NPC254558
0.9252	High Similarity	NPC470245
0.9184	High Similarity	NPC270590
0.9184	High Similarity	NPC301556
0.9184	High Similarity	NPC92293
0.9184	High Similarity	NPC266265
0.9184	High Similarity	NPC473215
0.9184	High Similarity	NPC471101
0.9184	High Similarity	NPC476975
0.9167	High Similarity	NPC182869
0.9116	High Similarity	NPC281717
0.911	High Similarity	NPC174982
0.911	High Similarity	NPC472556
0.911	High Similarity	NPC473088
0.911	High Similarity	NPC472571
0.911	High Similarity	NPC29704
0.911	High Similarity	NPC472575
0.911	High Similarity	NPC470157
0.911	High Similarity	NPC476973
0.911	High Similarity	NPC158663
0.911	High Similarity	NPC177940
0.911	High Similarity	NPC171525
0.911	High Similarity	NPC184817
0.911	High Similarity	NPC469349
0.911	High Similarity	NPC200471
0.911	High Similarity	NPC472572
0.911	High Similarity	NPC472568
0.911	High Similarity	NPC96903
0.911	High Similarity	NPC471104
0.911	High Similarity	NPC470159
0.911	High Similarity	NPC70403
0.9085	High Similarity	NPC476077
0.9067	High Similarity	NPC134685
0.9067	High Similarity	NPC219419
0.9067	High Similarity	NPC248265
0.9067	High Similarity	NPC11588
0.9067	High Similarity	NPC229545
0.9041	High Similarity	NPC11685
0.9041	High Similarity	NPC476974
0.9041	High Similarity	NPC470152
0.9041	High Similarity	NPC472569
0.9041	High Similarity	NPC475759
0.9041	High Similarity	NPC95265
0.9041	High Similarity	NPC472573
0.9041	High Similarity	NPC70716
0.9041	High Similarity	NPC25768
0.9041	High Similarity	NPC472570
0.9041	High Similarity	NPC188865
0.9041	High Similarity	NPC125106
0.9041	High Similarity	NPC241951
0.9041	High Similarity	NPC95810
0.9041	High Similarity	NPC163719
0.9041	High Similarity	NPC57628
0.9041	High Similarity	NPC475122
0.9007	High Similarity	NPC259144
0.9007	High Similarity	NPC114357
0.9007	High Similarity	NPC155329
0.8993	High Similarity	NPC91730
0.898	High Similarity	NPC471107
0.898	High Similarity	NPC471100
0.8973	High Similarity	NPC163087
0.8973	High Similarity	NPC477894
0.8973	High Similarity	NPC477468
0.8968	High Similarity	NPC295408
0.8968	High Similarity	NPC150893
0.8968	High Similarity	NPC329960
0.8966	High Similarity	NPC213567
0.8933	High Similarity	NPC197037
0.8924	High Similarity	NPC477466
0.8924	High Similarity	NPC477473
0.8924	High Similarity	NPC477469
0.8924	High Similarity	NPC477471
0.8912	High Similarity	NPC470231
0.8889	High Similarity	NPC469417
0.8882	High Similarity	NPC132599
0.8882	High Similarity	NPC473611
0.8882	High Similarity	NPC473632
0.8882	High Similarity	NPC469730
0.8861	High Similarity	NPC102465
0.8859	High Similarity	NPC217918
0.8851	High Similarity	NPC301946
0.8851	High Similarity	NPC277053
0.8846	High Similarity	NPC66193
0.8844	High Similarity	NPC270498
0.8844	High Similarity	NPC473673
0.8844	High Similarity	NPC147217
0.8844	High Similarity	NPC177340
0.8844	High Similarity	NPC246480
0.8844	High Similarity	NPC475429
0.8844	High Similarity	NPC139067
0.8844	High Similarity	NPC191082
0.8836	High Similarity	NPC472576
0.8836	High Similarity	NPC224491
0.8836	High Similarity	NPC87448
0.8836	High Similarity	NPC27377
0.8836	High Similarity	NPC118080
0.8836	High Similarity	NPC291599
0.8836	High Similarity	NPC41481
0.8836	High Similarity	NPC97947
0.8836	High Similarity	NPC16912
0.8831	High Similarity	NPC469399
0.8824	High Similarity	NPC11410
0.8792	High Similarity	NPC473602
0.8792	High Similarity	NPC474935
0.879	High Similarity	NPC471134
0.879	High Similarity	NPC471493
0.8784	High Similarity	NPC471912
0.8784	High Similarity	NPC80895
0.8784	High Similarity	NPC51314
0.8784	High Similarity	NPC67777
0.8776	High Similarity	NPC34012
0.8776	High Similarity	NPC472546
0.8767	High Similarity	NPC184747
0.8767	High Similarity	NPC43241
0.8767	High Similarity	NPC473758
0.8767	High Similarity	NPC147880
0.8767	High Similarity	NPC171207
0.8767	High Similarity	NPC473085
0.8767	High Similarity	NPC97667
0.8767	High Similarity	NPC473109
0.8767	High Similarity	NPC473112
0.8767	High Similarity	NPC100913
0.8767	High Similarity	NPC200592
0.8767	High Similarity	NPC472547
0.8767	High Similarity	NPC48017
0.8767	High Similarity	NPC4341
0.8767	High Similarity	NPC476094
0.8767	High Similarity	NPC90614
0.8767	High Similarity	NPC275592
0.8767	High Similarity	NPC473081
0.8767	High Similarity	NPC211137
0.8767	High Similarity	NPC473613
0.8767	High Similarity	NPC473060
0.8758	High Similarity	NPC251139
0.875	High Similarity	NPC477896
0.875	High Similarity	NPC477893
0.8742	High Similarity	NPC469420
0.8734	High Similarity	NPC61891
0.8716	High Similarity	NPC91703
0.871	High Similarity	NPC472807
0.8699	High Similarity	NPC214550
0.8699	High Similarity	NPC210591
0.8699	High Similarity	NPC475652
0.8667	High Similarity	NPC477737
0.8667	High Similarity	NPC475552
0.8662	High Similarity	NPC55744
0.8645	High Similarity	NPC477735
0.8642	High Similarity	NPC469421
0.8639	High Similarity	NPC477904
0.8639	High Similarity	NPC183270
0.863	High Similarity	NPC283375
0.863	High Similarity	NPC39549
0.863	High Similarity	NPC183122
0.8627	High Similarity	NPC138641
0.8627	High Similarity	NPC283875
0.8627	High Similarity	NPC469647
0.8627	High Similarity	NPC22571

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 NPC237549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	788
0.2-0.3	1541
0.3-0.4	2858
0.4-0.5	2221
0.5-0.6	1071
0.6-0.7	305
0.7-0.8	77
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD7236	Approved
0.8204	Intermediate Similarity	NPD8368	Discontinued
0.8187	Intermediate Similarity	NPD8360	Approved
0.8187	Intermediate Similarity	NPD8361	Approved
0.8187	Intermediate Similarity	NPD8435	Approved
0.8182	Intermediate Similarity	NPD7799	Discontinued
0.8114	Intermediate Similarity	NPD8485	Approved
0.8089	Intermediate Similarity	NPD7239	Suspended
0.807	Intermediate Similarity	NPD8434	Phase 2
0.8059	Intermediate Similarity	NPD8407	Phase 2
0.7978	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD8150	Discontinued
0.7886	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7057	Phase 3
0.7636	Intermediate Similarity	NPD7058	Phase 2
0.7632	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8312	Approved
0.7586	Intermediate Similarity	NPD8313	Approved
0.7532	Intermediate Similarity	NPD8166	Discontinued
0.7515	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8319	Approved
0.7514	Intermediate Similarity	NPD8320	Phase 1
0.7485	Intermediate Similarity	NPD7458	Discontinued
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7484	Intermediate Similarity	NPD6190	Approved
0.7473	Intermediate Similarity	NPD7700	Phase 2
0.7473	Intermediate Similarity	NPD7699	Phase 2
0.7472	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7961	Discontinued
0.7439	Intermediate Similarity	NPD6599	Discontinued
0.7434	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4628	Phase 3
0.7414	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7819	Suspended
0.7403	Intermediate Similarity	NPD6535	Approved
0.7403	Intermediate Similarity	NPD6534	Approved
0.7384	Intermediate Similarity	NPD7473	Discontinued
0.7366	Intermediate Similarity	NPD7435	Discontinued
0.7349	Intermediate Similarity	NPD6801	Discontinued
0.7333	Intermediate Similarity	NPD4380	Phase 2
0.7326	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6166	Phase 2
0.7326	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7008	Discontinued
0.7299	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2629	Approved
0.7262	Intermediate Similarity	NPD5402	Approved
0.7262	Intermediate Similarity	NPD3817	Phase 2
0.7251	Intermediate Similarity	NPD8127	Discontinued
0.7241	Intermediate Similarity	NPD4198	Discontinued
0.7234	Intermediate Similarity	NPD7871	Phase 2
0.7234	Intermediate Similarity	NPD7870	Phase 2
0.7225	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7874	Approved
0.7219	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6232	Discontinued
0.7209	Intermediate Similarity	NPD3787	Discontinued
0.7204	Intermediate Similarity	NPD6781	Approved
0.7204	Intermediate Similarity	NPD6782	Approved
0.7204	Intermediate Similarity	NPD6776	Approved
0.7204	Intermediate Similarity	NPD6778	Approved
0.7204	Intermediate Similarity	NPD6777	Approved
0.7204	Intermediate Similarity	NPD6780	Approved
0.7204	Intermediate Similarity	NPD6779	Approved
0.72	Intermediate Similarity	NPD5844	Phase 1
0.7181	Intermediate Similarity	NPD7698	Approved
0.7181	Intermediate Similarity	NPD7697	Approved
0.7181	Intermediate Similarity	NPD7696	Phase 3
0.7178	Intermediate Similarity	NPD6799	Approved
0.716	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5403	Approved
0.715	Intermediate Similarity	NPD8462	Phase 1
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7135	Intermediate Similarity	NPD7808	Phase 3
0.7134	Intermediate Similarity	NPD5401	Approved
0.7126	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7701	Phase 2
0.7099	Intermediate Similarity	NPD7003	Approved
0.7098	Intermediate Similarity	NPD7801	Approved
0.7091	Intermediate Similarity	NPD6273	Approved
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7083	Intermediate Similarity	NPD7411	Suspended
0.7079	Intermediate Similarity	NPD7251	Discontinued
0.7076	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3226	Approved
0.7062	Intermediate Similarity	NPD7074	Phase 3
0.7052	Intermediate Similarity	NPD6959	Discontinued
0.7039	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6797	Phase 2
0.7019	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD7054	Approved
0.7005	Intermediate Similarity	NPD8404	Phase 2
0.7	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8455	Phase 2
0.7	Intermediate Similarity	NPD5760	Phase 2
0.6994	Remote Similarity	NPD5494	Approved
0.6983	Remote Similarity	NPD7685	Pre-registration
0.698	Remote Similarity	NPD7741	Discontinued
0.697	Remote Similarity	NPD7390	Discontinued
0.6966	Remote Similarity	NPD7472	Approved
0.695	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3818	Discontinued
0.6949	Remote Similarity	NPD7228	Approved
0.6943	Remote Similarity	NPD3764	Approved
0.6941	Remote Similarity	NPD37	Approved
0.6941	Remote Similarity	NPD1934	Approved
0.6939	Remote Similarity	NPD5951	Approved
0.6936	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4966	Approved
0.6919	Remote Similarity	NPD3882	Suspended
0.6919	Remote Similarity	NPD4965	Approved
0.6919	Remote Similarity	NPD4967	Phase 2
0.6914	Remote Similarity	NPD2346	Discontinued
0.6911	Remote Similarity	NPD7497	Discontinued
0.6903	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6764	Approved
0.6889	Remote Similarity	NPD6765	Approved
0.6887	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6213	Phase 3
0.6882	Remote Similarity	NPD6212	Phase 3
0.6882	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6823	Phase 2
0.6852	Remote Similarity	NPD5408	Approved
0.6852	Remote Similarity	NPD5405	Approved
0.6852	Remote Similarity	NPD5406	Approved
0.6852	Remote Similarity	NPD5404	Approved
0.6839	Remote Similarity	NPD6234	Discontinued
0.6839	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2533	Approved
0.6826	Remote Similarity	NPD2534	Approved
0.6826	Remote Similarity	NPD2532	Approved
0.6813	Remote Similarity	NPD230	Phase 1
0.6802	Remote Similarity	NPD2801	Approved
0.6796	Remote Similarity	NPD6559	Discontinued
0.6796	Remote Similarity	NPD7240	Approved
0.679	Remote Similarity	NPD2799	Discontinued
0.6782	Remote Similarity	NPD3749	Approved
0.6781	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5126	Approved
0.6776	Remote Similarity	NPD5125	Phase 3
0.6776	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2182	Approved
0.6748	Remote Similarity	NPD2796	Approved
0.6746	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6784	Approved
0.6739	Remote Similarity	NPD6785	Approved
0.6732	Remote Similarity	NPD8328	Phase 3
0.673	Remote Similarity	NPD2313	Discontinued
0.6728	Remote Similarity	NPD7097	Phase 1
0.6711	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6355	Discontinued
0.6707	Remote Similarity	NPD7266	Discontinued
0.6705	Remote Similarity	NPD1465	Phase 2
0.6702	Remote Similarity	NPD8285	Discontinued
0.669	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7610	Discontinued
0.6688	Remote Similarity	NPD6287	Discontinued
0.6687	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3750	Approved
0.6686	Remote Similarity	NPD1512	Approved
0.6685	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5048	Discontinued
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7199	Phase 2
0.6647	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2935	Discontinued
0.6644	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6010	Discontinued
0.6625	Remote Similarity	NPD6798	Discontinued
0.6624	Remote Similarity	NPD1470	Approved
0.6623	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3300	Phase 2
0.6606	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1237	Approved
0.6585	Remote Similarity	NPD7033	Discontinued
0.6585	Remote Similarity	NPD3748	Approved
0.6585	Remote Similarity	NPD7305	Phase 1

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