NPASS Compound

Structure

NPC18950 OpenBabel06302215522D 45 48 0 0 1 0 0 0 0 0999 V2000 2.2321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3660 -4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3660 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2321 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0981 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.6962 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.5622 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.4282 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.4282 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.2942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.0263 -4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.8923 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.8923 -6.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.0263 -6.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.1603 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0263 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -8.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.1603 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5670 -8.9135 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 8.8238 -9.5827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.9578 -9.0827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.0443 -9.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2353 -8.9016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1657 -8.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9284 -10.5772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5451 -9.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7583 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7583 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0263 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 45 1 0 0 0 0 2 41 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 3 44 1 0 0 0 0 4 5 1 0 0 0 0 4 43 1 0 0 0 0 5 6 1 0 0 0 0 5 42 1 0 0 0 0 6 7 1 0 0 0 0 6 41 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 37 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 10 40 1 0 0 0 0 11 12 1 0 0 0 0 11 39 1 0 0 0 0 12 13 1 0 0 0 0 12 38 1 0 0 0 0 13 14 1 0 0 0 0 13 37 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 21 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 17 36 1 0 0 0 0 18 19 1 0 0 0 0 18 35 1 0 0 0 0 19 20 1 0 0 0 0 19 34 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 22 23 1 0 0 0 0 23 31 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 24 25 1 0 0 0 0 26 27 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 32 1 0 0 0 0 28 29 1 0 0 0 0 28 31 1 0 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	666.22
Volume:	574.029
LogP:	-5.023
LogD:	-3.221
LogS:	0.756
# Rotatable Bonds:	11
TPSA:	347.83
# H-Bond Aceptor:	21
# H-Bond Donor:	14
# Rings:	4
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.097
Synthetic Accessibility Score:	5.362
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.407
MDCK Permeability:	0.001074104686267674
Pgp-inhibitor:	0.001
Pgp-substrate:	0.902
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.401
Plasma Protein Binding (PPB):	4.027926921844482%
Volume Distribution (VD):	-0.055
Pgp-substrate:	58.81406021118164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.001
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	0.407
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.136
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.006
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.002

Download Data

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

Natural Product: NPC18950

Natural Product ID:	NPC18950
*Common Name:**	KUVZQLSUXDNGAW-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KUVZQLSUXDNGAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H42O21.4H2O/c25-1-6-10(28)14(32)17(35)21(41-6)39-3-8-11(29)15(33)18(36)22(42-8)40-4-9-12(30)16(34)19(37)23(43-9)45-24(5-27)20(38)13(31)7(2-26)44-24;;;;/h6-23,25-38H,1-5H2;4*1H2
SMILES:	C(C1C(C(C(C(OCC2C(C(C(C(OCC3C(C(C(C(O3)OC3(CO)C(C(C(CO)O3)O)O)O)O)O)O2)O)O)O)O1)O)O)O)O.O.O.O.O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	19706252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12232319]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30707	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724855]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21375312]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22208890]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	aerial parts and buds	Cagliari, Sardinia	2012-FEB	PMID[22769561]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27653	Lablab niger	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30707	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16066	Urtica cannabina	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14715	Trollius chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3106	Sabia schumanniana	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27653	Lablab niger	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14715	Trollius chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16066	Urtica cannabina	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3106	Sabia schumanniana	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1099	Capparis spinosa	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16066	Urtica cannabina	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30707	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3106	Sabia schumanniana	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27653	Lablab niger	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3106	Sabia schumanniana	Species	Sabiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21824	Lycopus lucidus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14715	Trollius chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16066	Urtica cannabina	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25909	Leonurus sibiricus	Species	Lamiaceae	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 NPC18950 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	928
0.1-0.2	9411
0.2-0.3	15941
0.3-0.4	9673
0.4-0.5	4379
0.5-0.6	1889
0.6-0.7	390
0.7-0.8	65
0.8-0.85	18
0.85-0.9	0
0.9-0.95	3
0.95-1	0

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 NPC18950 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	949
0.1-0.2	5554
0.2-0.3	1800
0.3-0.4	500
0.4-0.5	223
0.5-0.6	74
0.6-0.7	29
0.7-0.8	10
0.8-0.85	10
0.85-0.9	1
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