NPASS Compound

Structure

NPC4942 OpenBabel06302216162D 32 36 0 0 1 0 0 0 0 0999 V2000 1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6852 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2131 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2131 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3705 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2131 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0557 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8983 2.4324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8983 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8713 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3848 0.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0557 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0557 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2131 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3705 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7410 2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 2 29 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 28 1 0 0 0 0 5 6 1 0 0 0 0 5 31 1 1 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 25 1 0 0 0 0 8 9 1 6 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 13 12 1 1 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 22 1 0 0 0 0 14 15 1 1 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 22 23 1 1 0 0 0 23 24 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 1 0 0 0 28 10 1 1 0 0 0 28 29 1 0 0 0 0 29 30 1 1 0 0 0 31 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	499.598
LogP:	6.648
LogD:	5.299
LogS:	-5.774
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	4.823
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.117
MDCK Permeability:	9.453789971303195e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	97.18340301513672%
Volume Distribution (VD):	1.043
Pgp-substrate:	1.4375337362289429%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.205
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.893
CYP3A4-substrate:	0.692

ADMET: Excretion

Clearance (CL):	7.197
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.146
Carcinogencity:	0.025
Eye Corrosion:	0.104
Eye Irritation:	0.161
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC4942

Natural Product ID:	NPC4942
*Common Name:**	XUARCIYIVXVTAE-PAZHQPHASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUARCIYIVXVTAE-PAZHQPHASA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3/t19-,20+,22+,23-,24+,25-,27+,28-,29-,30-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@H]2[C@H]1C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO22761	Gentiana cruciata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)88887-1]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO14117	Diplodia sapinea	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075753]
NPO24512	Xestospongia testudinaria	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543913]
NPO25046	Aplidium meridianum	Species	Polyclinidae	Eukaryota	n.a.	South Georgia Islands, South Atlantic	n.a.	PMID[15026054]
NPO15432	Sarcodon aspratus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15665489]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17311456]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25391	Vitex glabrata	Species	Lamiaceae	Eukaryota	leaves	Chantaburi Province, Thailand	2007-Nov	PMID[19943620]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO28887	Eupomatia laurina	Species	Eupomatiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504145]
NPO14752	Sinopodophyllum emodi	Species	Berberidaceae	Eukaryota	roots and rhizomes	n.a.	n.a.	PMID[21570846]
NPO24745	Salvia cavaleriei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24256484]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128898]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28841316]
NPO22780	Sphaeranthus africanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30074787]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO25046	Aplidium meridianum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748381]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3860	Allium victorialis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13767	Woodfordia fruticosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24077	Astragalus pterocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13767	Woodfordia fruticosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3860	Allium victorialis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5517	Rhododendron tomentosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24077	Astragalus pterocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24601	Rumex dentatus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3860	Allium victorialis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22293	Bryobium hyacinthoides	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11880	Latua pubiflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO238	Lobelia st	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25145	Cydonia oblonga	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4485	Lamellodysidea herbacea	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24512	Xestospongia testudinaria	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14661	Blepharis sindica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13588	Sanguinaria canadensis	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23568	Guatteria pogonopus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25391	Vitex glabrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12622	Rudbeckia hirta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15240	Saracha viscosa	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25416	Uncaria cordata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15150	Phebalium gracile	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9283	Trichia favoginea	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13289	Frullania brittoniae	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18842	Gnaphalium gaudichaudianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14035	Cladosporium tenuissimum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14156	Fragaria indica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25046	Aplidium meridianum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25364	Didemnum candidum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3200	Arthrophytum leptocladum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5517	Rhododendron tomentosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15432	Sarcodon aspratus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3860	Allium victorialis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24077	Astragalus pterocarpus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6239	Corbicula fluminea	Species	Corbiculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13767	Woodfordia fruticosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5027	Peniophora polygonia	Species	Peniophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25625	Hymenophyllum recurvum	Species	Hymenophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22780	Sphaeranthus africanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25091	Samadera bidwillii	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14271	Spongia australis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15616	Solanum toxicarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO890	Remijia pedunculata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11098	Stelletta inconspicua	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14117	Diplodia sapinea	Species	Botryosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25700	Psiadia punctulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14752	Sinopodophyllum emodi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24745	Salvia cavaleriei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27957.1	Pinus densiflora var. densiflora	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28887	Eupomatia laurina	Species	Eupomatiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22761	Gentiana cruciata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8834	Cellulomonas biazotea	Species	Cellulomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24601	Rumex dentatus	Species	Polygonaceae	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 NPC4942 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	202
0.1-0.2	1777
0.2-0.3	7632
0.3-0.4	16546
0.4-0.5	6645
0.5-0.6	4819
0.6-0.7	3455
0.7-0.8	1198
0.8-0.85	254
0.85-0.9	125
0.9-0.95	16
0.95-1	28

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 NPC4942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	2037
0.2-0.3	4224
0.3-0.4	1935
0.4-0.5	399
0.5-0.6	188
0.6-0.7	158
0.7-0.8	16
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

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