NPASS Compound

Structure

NPC229991 OpenBabel06302215372D 28 31 0 0 1 0 0 0 0 0999 V2000 -2.5301 -0.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6812 0.0243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8452 -0.4732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8580 -1.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0256 -1.9371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8196 -1.4639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6508 -1.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5063 -1.4862 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5191 -0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3690 -0.0331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1997 -0.5398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1869 -1.5083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3433 -1.9817 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3305 -2.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3633 -2.9363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8031 -3.7931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3084 -4.6244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3819 0.9413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5333 1.4312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6894 0.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6765 -0.0107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8324 -0.4953 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 0.0128 0.9728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8603 1.4570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5197 2.3597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5460 2.3959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 2.8893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 23 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 22 2 0 0 0 0 6 7 1 0 0 0 0 8 7 1 6 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 21 2 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 25 26 1 0 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	141.07
Volume:	167.199
LogP:	3.368
LogD:	2.997
LogS:	-4.054
# Rotatable Bonds:	0
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.521
Synthetic Accessibility Score:	3.14
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.578
MDCK Permeability:	2.340555511182174e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668
Plasma Protein Binding (PPB):	94.56983184814453%
Volume Distribution (VD):	1.205
Pgp-substrate:	5.4434404373168945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.673
CYP2C19-substrate:	0.29
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.399
CYP2D6-inhibitor:	0.171
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	8.501
Half-life (T1/2):	0.502

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.384
Drug-inuced Liver Injury (DILI):	0.772
AMES Toxicity:	0.762
Rat Oral Acute Toxicity:	0.864
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.928
Carcinogencity:	0.832
Eye Corrosion:	0.361
Eye Irritation:	0.977
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC229991

Natural Product ID:	NPC229991
*Common Name:**	JWSAYTXQWHOMHU-CYBMUJFWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JWSAYTXQWHOMHU-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C21H23NO6/c1-25-14-6-5-11-9-13-16-12(7-8-22(13)21(24)28-4)10-15(26-2)20(27-3)18(16)17(11)19(14)23/h5-6,10,13,23H,7-9H2,1-4H3/t13-/m1/s1
SMILES:	COc1ccc2C[C@@H]3c4c(CCN3C(=O)OC)cc(c(c4-c2c1O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	5320994
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50053a043]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[10075775]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479331]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11325235]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[14575439]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15387664]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26238319]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277309]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[9428162]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19709	Pseudocyphellaria australiensis	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26361	Annona cherimolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8172	Emericellopsis minima	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18533	Delisea elegans	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17630	Helenium integrifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17499	Bursera kerberi	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16325	Sideritis dasygnaphala	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19170	Lasianthaea podocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15127	Senecio congestus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12223	Stellaria media	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	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 NPC229991 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	276
0.1-0.2	1440
0.2-0.3	6373
0.3-0.4	11649
0.4-0.5	5168
0.5-0.6	11301
0.6-0.7	5337
0.7-0.8	792
0.8-0.85	217
0.85-0.9	99
0.9-0.95	36
0.95-1	9

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 NPC229991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	720
0.2-0.3	1050
0.3-0.4	1984
0.4-0.5	2609
0.5-0.6	1774
0.6-0.7	655
0.7-0.8	152
0.8-0.85	20
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