NPASS Compound

Structure

NPC296985 OpenBabel06302216222D 41 45 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7026 -0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -1.1636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9898 -1.7514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -0.7569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9033 -1.3446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5116 -1.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7195 -2.8849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 2 1 1 0 0 0 3 4 1 0 0 0 0 3 40 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 1 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 7 13 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 18 1 0 0 0 0 9 10 2 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 19 26 1 0 0 0 0 19 20 2 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 25 26 2 0 0 0 0 27 28 1 6 0 0 0 27 38 1 0 0 0 0 29 28 1 1 0 0 0 29 30 1 0 0 0 0 29 36 1 0 0 0 0 30 31 1 0 0 0 0 31 32 1 0 0 0 0 32 33 1 6 0 0 0 32 34 1 0 0 0 0 32 36 1 0 0 0 0 34 35 1 0 0 0 0 36 37 1 6 0 0 0 38 39 1 1 0 0 0 38 40 1 0 0 0 0 40 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.14
Volume:	526.232
LogP:	0.189
LogD:	-0.213
LogS:	-3.835
# Rotatable Bonds:	7
TPSA:	249.2
# H-Bond Aceptor:	15
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	4.724
Fsp3:	0.423
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.471
MDCK Permeability:	1.1659680239972658e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.942
20% Bioavailability (F20%):	0.627
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	86.71915435791016%
Volume Distribution (VD):	0.578
Pgp-substrate:	12.453356742858887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.021

ADMET: Excretion

Clearance (CL):	1.569
Half-life (T1/2):	0.798

ADMET: Toxicity

hERG Blockers:	0.41
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.752
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.924
Carcinogencity:	0.235
Eye Corrosion:	0.003
Eye Irritation:	0.127
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC296985

Natural Product ID:	NPC296985
*Common Name:**	YSXNEFJASLJGTK-YRCFQSNFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YSXNEFJASLJGTK-YRCFQSNFSA-N
Standard InCHI:	InChI=1S/C26H28O15/c27-7-18-20(33)21(34)22(41-25-23(35)26(36,8-28)9-37-25)24(40-18)38-11-4-14(31)19-15(32)6-16(39-17(19)5-11)10-1-2-12(29)13(30)3-10/h1-6,18,20-25,27-31,33-36H,7-9H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1
SMILES:	c1cc(c(cc1c1cc(=O)c2c(cc(cc2o1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@](CO)(CO1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101248035
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	callus	n.a.	PMID[10552648]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350171]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	Green Island, Taiwan	2002-MAY	PMID[16180809]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17268112]
NPO6365	Pachychalina alcaloidifera	Species	Niphatidae	Eukaryota	n.a.	Brazilian	n.a.	PMID[17346073]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18214349]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19778086]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	leaves	n.a.	n.a.	PMID[20634065]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24895781]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	flower buds	n.a.	n.a.	PMID[25987378]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[6893493]
NPO157	Convallaria majalis	Species	Asparagaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[6893493]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf Wax	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25123	Scutellaria sieberi	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26387	Linum crispum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5227	Lawsonia inermis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6365	Pachychalina alcaloidifera	Species	Niphatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12078	Teclea nobilis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25071	Aspergillus albus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26919	Sanguisorba officinalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8710	Licaria brasiliensis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25444	Christisonia bicolor	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8830	Crotalaria orixensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6749	Bergenia crassifolia	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1763	Rabdosia angustifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1068	Platytaenia lasiocarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26501	Palafoxia texana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21533	Smilax bracteata	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1420	Tenebrio obscurus	Species	Tenebrionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO832	Pseudocinchona pachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26056	Atroxima liberica	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2352	Tynanthus panurensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25198	Octopus vulgaris	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO157	Convallaria majalis	Species	Asparagaceae	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
NPO26721	NPC296985	Other	n.a.	632	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO26721	NPC296985	Raw	n.a.	6.300000509	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

☑ 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 NPC296985 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	454
0.1-0.2	1751
0.2-0.3	3689
0.3-0.4	9082
0.4-0.5	9472
0.5-0.6	4510
0.6-0.7	5472
0.7-0.8	5565
0.8-0.85	1824
0.85-0.9	556
0.9-0.95	316
0.95-1	6

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 NPC296985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	884
0.2-0.3	1881
0.3-0.4	2729
0.4-0.5	1922
0.5-0.6	929
0.6-0.7	279
0.7-0.8	116
0.8-0.85	19
0.85-0.9	5
0.9-0.95	7
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