NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	254.401
LogP:	3.921
LogD:	3.573
LogS:	-3.69
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.668
Synthetic Accessibility Score:	4.398
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.577
MDCK Permeability:	1.829317261581309e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.323
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.754
30% Bioavailability (F30%):	0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.783
Plasma Protein Binding (PPB):	75.77870178222656%
Volume Distribution (VD):	1.662
Pgp-substrate:	27.824665069580078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.574
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.375
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.563
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	10.408
Half-life (T1/2):	0.257

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.747
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.385
Carcinogencity:	0.937
Eye Corrosion:	0.78
Eye Irritation:	0.954
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC96484

Natural Product ID:	NPC96484
*Common Name:**	(1S,4R,4As,6R)-4,4A-Dimethyl-6-Prop-1-En-2-Yl-2,3,4,5,6,7-Hexahydro-1H-Naphthalen-1-Ol
IUPAC Name:	(1S,4R,4aS,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalen-1-ol
Synonyms:
Standard InCHIKey:	NJWPLFBOSCSZFA-UXOAXIEHSA-N
Standard InCHI:	InChI=1S/C15H24O/c1-10(2)12-6-7-13-14(16)8-5-11(3)15(13,4)9-12/h7,11-12,14,16H,1,5-6,8-9H2,2-4H3/t11-,12-,14+,15+/m1/s1
SMILES:	CC(=C)[C@@H]1CC=C2[C@](C1)(C)[C@H](C)CC[C@@H]2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489541
PubChem CID:	44576208
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(81)85171-0]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[11141121]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11514174]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	fruit	Hainan Island, China	1998	PMID[12398545]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18057725]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22277277]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23583435]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	PMID[24669201]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25757283]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9157192]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24874	Croton geayi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23657	Ophiocordyceps heteropoda	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27093	Kniphofia foliosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23837	Rubus laciniatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19716	Uvaria lucida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18875	Aconitum contortum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25226	Kalanchoe spathulata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21483	0nomuraea dietziae	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24969	Ageratum mexicanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24268	Pteryxia terebinthina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24589	Grindelia discoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24118	Buxus hildebrandtii	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21799	Bacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22924	Bombus terrestris	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25031	Petunia nyctaginiflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24021	Eucryphia cordifolia	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO25068	Zebrina pendula	Species	Enidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17445	Streptomyces corchorusii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28259	Viguiera pinnatilobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23660	Alpinia zerumbet	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23375	Hypericum reptans	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24456	Salvia lavandulifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21242	Neolitsea villosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24493	Echinacea simulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24191	Drypetes tessmanniana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18045	Holothuria atra	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27277	Stenocarpella maydis	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24937	Callicarpa acuminata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24754	Tsitsikamma favus	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25130	Hylotrupes bajulus	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24813	Agardhiella tenera	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23750	Escontria chiotilla	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24406	Rhizophora tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24688	Streptomyces ramocissimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24659	Eremurus chinensis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23149	Callistemon coccineus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13455	Hemiselmis virescens	Species	Hemiselmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	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

Activity Type	# Activity
IC50	1
Others	7

Activity Type	# Activity
Cell Line	3
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-9.2	%	PMID[512942]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-8.0	%	PMID[512942]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	-5.0	%	PMID[512942]
NPT2	Others	Unspecified		Inhibition	=	65.3	%	PMID[512942]
NPT2	Others	Unspecified		Inhibition	=	5.8	%	PMID[512942]
NPT2	Others	Unspecified		Inhibition	=	1.8	%	PMID[512942]
NPT2	Others	Unspecified		Inhibition	=	31.0	%	PMID[512942]
NPT2	Others	Unspecified		IC50	=	48000.0	nM	PMID[512942]

☑ 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 NPC96484 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	163
0.1-0.2	1390
0.2-0.3	6535
0.3-0.4	16454
0.4-0.5	9117
0.5-0.6	5724
0.6-0.7	2531
0.7-0.8	652
0.8-0.85	99
0.85-0.9	29
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9242	High Similarity	NPC474248
0.9104	High Similarity	NPC34834
0.9077	High Similarity	NPC202017
0.9062	High Similarity	NPC96793
0.9062	High Similarity	NPC323424
0.8971	High Similarity	NPC23954
0.8939	High Similarity	NPC171225
0.8841	High Similarity	NPC220939
0.8841	High Similarity	NPC265485
0.8824	High Similarity	NPC92801
0.8806	High Similarity	NPC208999
0.8806	High Similarity	NPC471238
0.8769	High Similarity	NPC68656
0.8732	High Similarity	NPC265588
0.8732	High Similarity	NPC253190
0.8714	High Similarity	NPC201048
0.8714	High Similarity	NPC476366
0.8714	High Similarity	NPC306727
0.8696	High Similarity	NPC477792
0.8696	High Similarity	NPC164022
0.8676	High Similarity	NPC471560
0.8657	High Similarity	NPC114651
0.863	High Similarity	NPC209430
0.863	High Similarity	NPC30986
0.8615	High Similarity	NPC81615
0.8611	High Similarity	NPC470711
0.8611	High Similarity	NPC91594
0.8611	High Similarity	NPC470758
0.8571	High Similarity	NPC182717
0.8514	High Similarity	NPC295131
0.8507	High Similarity	NPC475897
0.8493	Intermediate Similarity	NPC83351
0.8493	Intermediate Similarity	NPC167891
0.8493	Intermediate Similarity	NPC476314
0.8485	Intermediate Similarity	NPC107540
0.8485	Intermediate Similarity	NPC225415
0.8472	Intermediate Similarity	NPC470749
0.8472	Intermediate Similarity	NPC244488
0.8472	Intermediate Similarity	NPC247325
0.8451	Intermediate Similarity	NPC469534
0.8451	Intermediate Similarity	NPC100334
0.8451	Intermediate Similarity	NPC469593
0.8451	Intermediate Similarity	NPC469533
0.8429	Intermediate Similarity	NPC471271
0.8429	Intermediate Similarity	NPC167706
0.8429	Intermediate Similarity	NPC471272
0.8429	Intermediate Similarity	NPC110799
0.8429	Intermediate Similarity	NPC471268
0.84	Intermediate Similarity	NPC476646
0.8382	Intermediate Similarity	NPC68703
0.8382	Intermediate Similarity	NPC69649
0.8378	Intermediate Similarity	NPC47982
0.8378	Intermediate Similarity	NPC143182
0.8378	Intermediate Similarity	NPC109546
0.8378	Intermediate Similarity	NPC28862
0.8378	Intermediate Similarity	NPC84694
0.8378	Intermediate Similarity	NPC81306
0.8356	Intermediate Similarity	NPC203403
0.8333	Intermediate Similarity	NPC83200
0.8333	Intermediate Similarity	NPC32832
0.8333	Intermediate Similarity	NPC257347
0.8333	Intermediate Similarity	NPC141071
0.8333	Intermediate Similarity	NPC174956
0.8333	Intermediate Similarity	NPC471723
0.831	Intermediate Similarity	NPC471799
0.8308	Intermediate Similarity	NPC66020
0.8308	Intermediate Similarity	NPC240506
0.8289	Intermediate Similarity	NPC87489
0.8289	Intermediate Similarity	NPC202389
0.8286	Intermediate Similarity	NPC145498
0.8267	Intermediate Similarity	NPC96362
0.8267	Intermediate Similarity	NPC234193
0.8261	Intermediate Similarity	NPC245795
0.8261	Intermediate Similarity	NPC276616
0.8243	Intermediate Similarity	NPC474216
0.8243	Intermediate Similarity	NPC11908
0.8235	Intermediate Similarity	NPC279434
0.8235	Intermediate Similarity	NPC326310
0.8219	Intermediate Similarity	NPC290598
0.8219	Intermediate Similarity	NPC470362
0.8219	Intermediate Similarity	NPC27765
0.8219	Intermediate Similarity	NPC30590
0.8219	Intermediate Similarity	NPC265328
0.8219	Intermediate Similarity	NPC129165
0.8219	Intermediate Similarity	NPC202642
0.8219	Intermediate Similarity	NPC122418
0.8219	Intermediate Similarity	NPC134330
0.8219	Intermediate Similarity	NPC46160
0.8219	Intermediate Similarity	NPC189883
0.8219	Intermediate Similarity	NPC120098
0.8209	Intermediate Similarity	NPC290367
0.8194	Intermediate Similarity	NPC471797
0.8194	Intermediate Similarity	NPC477138
0.8194	Intermediate Similarity	NPC243342
0.8194	Intermediate Similarity	NPC91858
0.8182	Intermediate Similarity	NPC317458
0.8182	Intermediate Similarity	NPC194208
0.8182	Intermediate Similarity	NPC282694
0.8182	Intermediate Similarity	NPC79576
0.8169	Intermediate Similarity	NPC242001
0.8169	Intermediate Similarity	NPC242992
0.8158	Intermediate Similarity	NPC264245
0.8158	Intermediate Similarity	NPC23852
0.8158	Intermediate Similarity	NPC249423
0.8158	Intermediate Similarity	NPC209620
0.8143	Intermediate Similarity	NPC9942
0.8143	Intermediate Similarity	NPC473893
0.8133	Intermediate Similarity	NPC308038
0.8116	Intermediate Similarity	NPC197805
0.8108	Intermediate Similarity	NPC157996
0.8108	Intermediate Similarity	NPC90979
0.8108	Intermediate Similarity	NPC472805
0.8108	Intermediate Similarity	NPC214570
0.8108	Intermediate Similarity	NPC101475
0.8108	Intermediate Similarity	NPC34177
0.8108	Intermediate Similarity	NPC471798
0.8108	Intermediate Similarity	NPC40394
0.8108	Intermediate Similarity	NPC74995
0.8095	Intermediate Similarity	NPC130209
0.8095	Intermediate Similarity	NPC148216
0.8095	Intermediate Similarity	NPC148163
0.8088	Intermediate Similarity	NPC287339
0.8088	Intermediate Similarity	NPC258595
0.8082	Intermediate Similarity	NPC136188
0.8082	Intermediate Similarity	NPC35397
0.8082	Intermediate Similarity	NPC285893
0.8082	Intermediate Similarity	NPC69383
0.8082	Intermediate Similarity	NPC66566
0.8082	Intermediate Similarity	NPC322353
0.8082	Intermediate Similarity	NPC162742
0.8082	Intermediate Similarity	NPC138374
0.8082	Intermediate Similarity	NPC474946
0.8082	Intermediate Similarity	NPC230301
0.8082	Intermediate Similarity	NPC288035
0.8082	Intermediate Similarity	NPC133580
0.8082	Intermediate Similarity	NPC121744
0.8082	Intermediate Similarity	NPC34700
0.8082	Intermediate Similarity	NPC304309
0.8082	Intermediate Similarity	NPC118508
0.8082	Intermediate Similarity	NPC134847
0.8082	Intermediate Similarity	NPC22105
0.8082	Intermediate Similarity	NPC291503
0.8082	Intermediate Similarity	NPC28657
0.8082	Intermediate Similarity	NPC313179
0.8082	Intermediate Similarity	NPC477923
0.8082	Intermediate Similarity	NPC171148
0.8077	Intermediate Similarity	NPC474047
0.8077	Intermediate Similarity	NPC231310
0.8077	Intermediate Similarity	NPC238485
0.806	Intermediate Similarity	NPC473759
0.806	Intermediate Similarity	NPC474155
0.8056	Intermediate Similarity	NPC68443
0.8056	Intermediate Similarity	NPC474743
0.8056	Intermediate Similarity	NPC130665
0.8056	Intermediate Similarity	NPC474140
0.8052	Intermediate Similarity	NPC470049
0.8052	Intermediate Similarity	NPC189972
0.8052	Intermediate Similarity	NPC101462
0.8052	Intermediate Similarity	NPC49964
0.8052	Intermediate Similarity	NPC304285
0.8052	Intermediate Similarity	NPC218616
0.8052	Intermediate Similarity	NPC296701
0.8052	Intermediate Similarity	NPC50964
0.8052	Intermediate Similarity	NPC93590
0.8052	Intermediate Similarity	NPC155521
0.8026	Intermediate Similarity	NPC157895
0.8026	Intermediate Similarity	NPC209944
0.8026	Intermediate Similarity	NPC172013
0.8026	Intermediate Similarity	NPC104120
0.8026	Intermediate Similarity	NPC164840
0.8026	Intermediate Similarity	NPC471514
0.8026	Intermediate Similarity	NPC241290
0.8026	Intermediate Similarity	NPC148685
0.8026	Intermediate Similarity	NPC206062
0.8026	Intermediate Similarity	NPC113024
0.8026	Intermediate Similarity	NPC281880
0.8	Intermediate Similarity	NPC158662
0.8	Intermediate Similarity	NPC99168
0.8	Intermediate Similarity	NPC216460
0.8	Intermediate Similarity	NPC98386
0.8	Intermediate Similarity	NPC253807
0.8	Intermediate Similarity	NPC318136
0.8	Intermediate Similarity	NPC474989
0.8	Intermediate Similarity	NPC230295
0.8	Intermediate Similarity	NPC473943
0.8	Intermediate Similarity	NPC186191
0.8	Intermediate Similarity	NPC275910
0.8	Intermediate Similarity	NPC22955
0.8	Intermediate Similarity	NPC300499
0.8	Intermediate Similarity	NPC470396
0.8	Intermediate Similarity	NPC196753
0.8	Intermediate Similarity	NPC205455
0.7975	Intermediate Similarity	NPC109528
0.7973	Intermediate Similarity	NPC113733
0.7973	Intermediate Similarity	NPC300324
0.7973	Intermediate Similarity	NPC477925
0.7973	Intermediate Similarity	NPC106432
0.7973	Intermediate Similarity	NPC73875
0.7973	Intermediate Similarity	NPC321381
0.7973	Intermediate Similarity	NPC107059

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 NPC96484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1889
0.2-0.3	4063
0.3-0.4	2147
0.4-0.5	564
0.5-0.6	243
0.6-0.7	62
0.7-0.8	24
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8095	Intermediate Similarity	NPD342	Phase 1
0.8082	Intermediate Similarity	NPD6942	Approved
0.8082	Intermediate Similarity	NPD7339	Approved
0.8082	Intermediate Similarity	NPD8264	Approved
0.7973	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD368	Approved
0.7895	Intermediate Similarity	NPD7645	Phase 2
0.7564	Intermediate Similarity	NPD7525	Registered
0.7561	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6924	Approved
0.7467	Intermediate Similarity	NPD6926	Approved
0.7436	Intermediate Similarity	NPD6929	Approved
0.7432	Intermediate Similarity	NPD7151	Approved
0.7432	Intermediate Similarity	NPD7152	Approved
0.7432	Intermediate Similarity	NPD7150	Approved
0.7397	Intermediate Similarity	NPD6923	Approved
0.7397	Intermediate Similarity	NPD6922	Approved
0.7375	Intermediate Similarity	NPD3667	Approved
0.7342	Intermediate Similarity	NPD6930	Phase 2
0.7342	Intermediate Similarity	NPD6931	Approved
0.7308	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7144	Approved
0.7297	Intermediate Similarity	NPD7143	Approved
0.7273	Intermediate Similarity	NPD6933	Approved
0.7229	Intermediate Similarity	NPD3618	Phase 1
0.72	Intermediate Similarity	NPD4243	Approved
0.7195	Intermediate Similarity	NPD4786	Approved
0.7179	Intermediate Similarity	NPD5776	Phase 2
0.7179	Intermediate Similarity	NPD6925	Approved
0.7164	Intermediate Similarity	NPD4219	Approved
0.7125	Intermediate Similarity	NPD7509	Discontinued
0.7125	Intermediate Similarity	NPD4748	Discontinued
0.7125	Intermediate Similarity	NPD7332	Phase 2
0.7125	Intermediate Similarity	NPD7514	Phase 3
0.7089	Intermediate Similarity	NPD7145	Approved
0.7073	Intermediate Similarity	NPD6695	Phase 3
0.7037	Intermediate Similarity	NPD6902	Approved
0.7013	Intermediate Similarity	NPD4784	Approved
0.7013	Intermediate Similarity	NPD4785	Approved
0.6988	Remote Similarity	NPD3666	Approved
0.6988	Remote Similarity	NPD3665	Phase 1
0.6988	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3133	Approved
0.6977	Remote Similarity	NPD5328	Approved
0.6923	Remote Similarity	NPD5275	Approved
0.6923	Remote Similarity	NPD4190	Phase 3
0.6905	Remote Similarity	NPD6893	Approved
0.6829	Remote Similarity	NPD6898	Phase 1
0.6818	Remote Similarity	NPD7515	Phase 2
0.6818	Remote Similarity	NPD6079	Approved
0.675	Remote Similarity	NPD6932	Approved
0.6744	Remote Similarity	NPD7524	Approved
0.6744	Remote Similarity	NPD7750	Discontinued
0.6742	Remote Similarity	NPD4202	Approved
0.6706	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6628	Remote Similarity	NPD4519	Discontinued
0.6628	Remote Similarity	NPD5279	Phase 3
0.6628	Remote Similarity	NPD4623	Approved
0.6588	Remote Similarity	NPD3668	Phase 3
0.6585	Remote Similarity	NPD4195	Approved
0.6585	Remote Similarity	NPD6683	Phase 2
0.6562	Remote Similarity	NPD385	Approved
0.6562	Remote Similarity	NPD384	Approved
0.6559	Remote Similarity	NPD7638	Approved
0.6559	Remote Similarity	NPD4225	Approved
0.6526	Remote Similarity	NPD5211	Phase 2
0.6522	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD4697	Phase 3
0.6522	Remote Similarity	NPD5222	Approved
0.6522	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7748	Approved
0.6456	Remote Similarity	NPD4732	Discontinued
0.6452	Remote Similarity	NPD5173	Approved
0.6452	Remote Similarity	NPD4755	Approved
0.6444	Remote Similarity	NPD7087	Discontinued
0.6404	Remote Similarity	NPD4753	Phase 2
0.6392	Remote Similarity	NPD5141	Approved
0.6383	Remote Similarity	NPD5290	Discontinued
0.6374	Remote Similarity	NPD5778	Approved
0.6374	Remote Similarity	NPD6399	Phase 3
0.6374	Remote Similarity	NPD5779	Approved
0.6353	Remote Similarity	NPD4221	Approved
0.6353	Remote Similarity	NPD4223	Phase 3
0.6322	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD4700	Approved
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.631	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.631	Remote Similarity	NPD4695	Discontinued
0.6277	Remote Similarity	NPD7902	Approved
0.6265	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6411	Approved
0.6264	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD5223	Approved
0.6222	Remote Similarity	NPD6051	Approved
0.6207	Remote Similarity	NPD4197	Approved
0.6207	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5224	Approved
0.6186	Remote Similarity	NPD5225	Approved
0.6186	Remote Similarity	NPD5226	Approved
0.6186	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD7136	Phase 2
0.6136	Remote Similarity	NPD5329	Approved
0.6122	Remote Similarity	NPD5174	Approved
0.6122	Remote Similarity	NPD5175	Approved
0.6122	Remote Similarity	NPD4754	Approved
0.6082	Remote Similarity	NPD4159	Approved
0.6071	Remote Similarity	NPD3617	Approved
0.6067	Remote Similarity	NPD7146	Approved
0.6067	Remote Similarity	NPD4690	Approved
0.6067	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4689	Approved
0.6067	Remote Similarity	NPD5330	Approved
0.6067	Remote Similarity	NPD5205	Approved
0.6067	Remote Similarity	NPD4688	Approved
0.6067	Remote Similarity	NPD4694	Approved
0.6067	Remote Similarity	NPD7521	Approved
0.6067	Remote Similarity	NPD6409	Approved
0.6067	Remote Similarity	NPD5690	Phase 2
0.6067	Remote Similarity	NPD6684	Approved
0.6067	Remote Similarity	NPD4138	Approved
0.6067	Remote Similarity	NPD4693	Phase 3
0.6067	Remote Similarity	NPD7334	Approved
0.6067	Remote Similarity	NPD5280	Approved
0.6064	Remote Similarity	NPD4629	Approved
0.6064	Remote Similarity	NPD5210	Approved
0.6044	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD6101	Approved
0.602	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD4191	Approved
0.6	Remote Similarity	NPD4767	Approved
0.5977	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7900	Approved
0.5941	Remote Similarity	NPD5701	Approved
0.5941	Remote Similarity	NPD5697	Approved
0.5938	Remote Similarity	NPD6083	Phase 2
0.5938	Remote Similarity	NPD6084	Phase 2
0.5934	Remote Similarity	NPD4722	Approved
0.5934	Remote Similarity	NPD4723	Approved
0.5934	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD6903	Approved
0.593	Remote Similarity	NPD4819	Approved
0.593	Remote Similarity	NPD4820	Approved
0.593	Remote Similarity	NPD4822	Approved
0.593	Remote Similarity	NPD4821	Approved
0.5918	Remote Similarity	NPD5344	Discontinued
0.5909	Remote Similarity	NPD4788	Approved
0.5909	Remote Similarity	NPD5362	Discontinued
0.5909	Remote Similarity	NPD5332	Approved
0.5909	Remote Similarity	NPD5331	Approved
0.5909	Remote Similarity	NPD4265	Approved
0.5895	Remote Similarity	NPD5695	Phase 3
0.5888	Remote Similarity	NPD7115	Discovery
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD5168	Approved
0.5882	Remote Similarity	NPD6011	Approved
0.5882	Remote Similarity	NPD4271	Approved
0.5882	Remote Similarity	NPD5128	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD4729	Approved
0.5882	Remote Similarity	NPD9410	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4268	Approved
0.5875	Remote Similarity	NPD791	Approved
0.5875	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD15	Approved
0.5875	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD1145	Discontinued
0.5862	Remote Similarity	NPD4692	Approved
0.5862	Remote Similarity	NPD4139	Approved
0.5862	Remote Similarity	NPD4790	Discontinued
0.5833	Remote Similarity	NPD1346	Approved
0.5825	Remote Similarity	NPD6013	Approved
0.5825	Remote Similarity	NPD6373	Approved
0.5825	Remote Similarity	NPD6014	Approved
0.5825	Remote Similarity	NPD6012	Approved
0.5825	Remote Similarity	NPD6372	Approved
0.5824	Remote Similarity	NPD3573	Approved
0.5802	Remote Similarity	NPD4787	Phase 1
0.58	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4269	Approved
0.5795	Remote Similarity	NPD4270	Approved
0.5769	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5250	Approved
0.5769	Remote Similarity	NPD4634	Approved

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