NPASS Compound

Structure

NPC184045 OpenBabel06302215342D 49 53 0 0 1 0 0 0 0 0999 V2000 -9.2262 -1.0966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3194 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3194 -2.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6254 -3.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6439 -3.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2683 -4.0545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9499 -2.4537 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0999 -2.9444 0.0000 C 0 0 2 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 -4.2499 -1.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4000 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4185 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9092 -1.8315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2499 0.4907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0999 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0999 -0.9815 0.0000 C 0 0 2 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 -5.9499 -1.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6439 -0.7782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2683 0.1286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6254 -0.7782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7999 0.9815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7999 1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9499 2.4537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6499 2.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4999 1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3499 2.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3499 3.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4999 3.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6499 3.4352 0.0000 C 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 -3.4000 1.9630 0.0000 C 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 -3.4000 2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5500 0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 -0.9815 0.0000 O 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 -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 1.4722 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0999 -3.9259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2499 -4.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4000 -3.9259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2499 -5.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5474 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 22 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 7 19 1 0 0 0 0 7 8 1 0 0 0 0 7 49 1 1 0 0 0 8 9 1 0 0 0 0 8 45 1 6 0 0 0 10 9 1 1 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 14 15 1 0 0 0 0 14 36 1 6 0 0 0 15 16 1 0 0 0 0 15 32 1 6 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 1 0 0 0 17 19 1 0 0 0 0 19 20 1 1 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 23 24 1 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 26 31 2 0 0 0 0 26 27 1 0 0 0 0 27 28 2 0 0 0 0 28 29 1 0 0 0 0 29 30 2 0 0 0 0 30 31 1 0 0 0 0 32 33 1 0 0 0 0 33 34 2 0 0 0 0 33 35 1 0 0 0 0 36 37 1 0 0 0 0 37 38 2 0 0 0 0 37 39 1 0 0 0 0 39 44 2 0 0 0 0 39 40 1 0 0 0 0 40 41 2 0 0 0 0 41 42 1 0 0 0 0 42 43 2 0 0 0 0 43 44 1 0 0 0 0 45 46 1 0 0 0 0 46 47 2 0 0 0 0 46 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.23
Volume:	387.753
LogP:	-0.009
LogD:	-0.358
LogS:	-1.654
# Rotatable Bonds:	6
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	4.718
Fsp3:	0.895
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.404
MDCK Permeability:	4.9437283450970426e-05
Pgp-inhibitor:	0.095
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.444
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.715

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	79.23705291748047%
Volume Distribution (VD):	0.859
Pgp-substrate:	17.567882537841797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.476
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.405
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	1.49
Half-life (T1/2):	0.711

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.214
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.107
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.088
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC184045

Natural Product ID:	NPC184045
*Common Name:**	MFPAGFFHWQHANG-XVOGWUIDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MFPAGFFHWQHANG-XVOGWUIDSA-N
Standard InCHI:	InChI=1S/C38H42O11/c1-21-17-18-28(42)38(45)29(46-22(2)39)20-27-36(4,5)32(48-34(43)24-13-9-7-10-14-24)30(47-23(3)40)33(37(27,6)31(38)26(41)19-21)49-35(44)25-15-11-8-12-16-25/h7-17,27,29-33,45H,18-20H2,1-6H3/b21-17-/t27-,29+,30-,31+,32+,33-,37-,38-/m1/s1
SMILES:	CC1=CCC(=O)[C@]2([C@H](C[C@@H]3C(C)(C)[C@H]([C@H]([C@H]([C@@]3(C)[C@@H]2C(=O)C1)OC(=O)c1ccccc1)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids 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
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]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26473275]
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]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19451	Salvia prionitis	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]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
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]
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]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	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]
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]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21680	Saussurea triangulata	Species	Asteraceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC184045 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	1181
0.2-0.3	2482
0.3-0.4	4967
0.4-0.5	9518
0.5-0.6	10542
0.6-0.7	10292
0.7-0.8	2968
0.8-0.85	182
0.85-0.9	172
0.9-0.95	32
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID

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 NPC184045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	784
0.2-0.3	1525
0.3-0.4	2829
0.4-0.5	2238
0.5-0.6	1084
0.6-0.7	331
0.7-0.8	67
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

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