NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	2.554
LogD:	2.47
LogS:	-2.742
# Rotatable Bonds:	0
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	4.194
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.639
MDCK Permeability:	1.994190097320825e-05
Pgp-inhibitor:	0.786
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.072

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.486
Plasma Protein Binding (PPB):	85.82432556152344%
Volume Distribution (VD):	0.772
Pgp-substrate:	20.999740600585938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.154
CYP1A2-substrate:	0.686
CYP2C19-inhibitor:	0.216
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.123
CYP2D6-inhibitor:	0.186
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.471

ADMET: Excretion

Clearance (CL):	13.115
Half-life (T1/2):	0.749

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.24
Drug-inuced Liver Injury (DILI):	0.232
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.691
Maximum Recommended Daily Dose:	0.496
Skin Sensitization:	0.184
Carcinogencity:	0.613
Eye Corrosion:	0.014
Eye Irritation:	0.059
Respiratory Toxicity:	0.694

Download Data

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

Natural Product: NPC281138

Natural Product ID:	NPC281138
*Common Name:**	(4As,7S,8R)-8-Hydroxy-1,4A-Dimethyl-7-Prop-1-En-2-Yl-3,4,5,6,7,8-Hexahydronaphthalen-2-One
IUPAC Name:	(4aS,7S,8R)-8-hydroxy-1,4a-dimethyl-7-prop-1-en-2-yl-3,4,5,6,7,8-hexahydronaphthalen-2-one
Synonyms:
Standard InCHIKey:	OACKHCQOHPYTKY-GLQYFDAESA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9(2)11-5-7-15(4)8-6-12(16)10(3)13(15)14(11)17/h11,14,17H,1,5-8H2,2-4H3/t11-,14+,15-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(C)CCC(=O)C(=C2[C@@H]1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1949802
PubChem CID:	57393410
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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	n.a.	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[9157192]
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]
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]
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]
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[TCM_Taiwan]
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[TM-MC]
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]
NPO23375	Hypericum reptans	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24813	Agardhiella tenera	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21242	Neolitsea villosa	Species	Lauraceae	Eukaryota	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]
NPO24493	Echinacea simulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24406	Rhizophora tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24191	Drypetes tessmanniana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23478	Uncaria africana	Species	Rubiaceae	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]
NPO18045	Holothuria atra	Species	Holothuriidae	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]
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]
NPO19716	Uvaria lucida	Species	Annonaceae	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]
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]
NPO23149	Callistemon coccineus	Species	Myrtaceae	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]
NPO24874	Croton geayi	Species	Euphorbiaceae	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]
NPO1674	Dalbergia nitidula	Species	Fabaceae	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]
NPO23837	Rubus laciniatus	Species	Rosaceae	Eukaryota	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]
NPO24456	Salvia lavandulifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21483	0nomuraea dietziae	Species	Streptosporangiaceae	Bacteria	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]
NPO24589	Grindelia discoidea	Species	Asteraceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	12.52	ug.mL-1	PMID[520156]

☑ 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 NPC281138 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	162
0.1-0.2	1127
0.2-0.3	4895
0.3-0.4	12179
0.4-0.5	12077
0.5-0.6	6944
0.6-0.7	4223
0.7-0.8	1000
0.8-0.85	69
0.85-0.9	16
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9342	High Similarity	NPC172013
0.9211	High Similarity	NPC308038
0.92	High Similarity	NPC197659
0.9079	High Similarity	NPC178852
0.8861	High Similarity	NPC93590
0.8846	High Similarity	NPC104120
0.8846	High Similarity	NPC148685
0.8846	High Similarity	NPC157895
0.8816	High Similarity	NPC263582
0.875	High Similarity	NPC169941
0.875	High Similarity	NPC251475
0.8701	High Similarity	NPC74995
0.869	High Similarity	NPC473099
0.8659	High Similarity	NPC472974
0.8659	High Similarity	NPC472985
0.8659	High Similarity	NPC472986
0.8642	High Similarity	NPC40687
0.859	High Similarity	NPC475994
0.859	High Similarity	NPC62336
0.8588	High Similarity	NPC116726
0.8571	High Similarity	NPC473100
0.8571	High Similarity	NPC472983
0.8537	High Similarity	NPC15807
0.8533	High Similarity	NPC84790
0.8519	High Similarity	NPC64600
0.85	High Similarity	NPC470298
0.8481	Intermediate Similarity	NPC152061
0.8471	Intermediate Similarity	NPC134321
0.8471	Intermediate Similarity	NPC48010
0.8462	Intermediate Similarity	NPC203403
0.8462	Intermediate Similarity	NPC266193
0.8462	Intermediate Similarity	NPC34110
0.8462	Intermediate Similarity	NPC257666
0.8434	Intermediate Similarity	NPC82979
0.8434	Intermediate Similarity	NPC473226
0.8434	Intermediate Similarity	NPC194417
0.8434	Intermediate Similarity	NPC470955
0.8421	Intermediate Similarity	NPC247586
0.8391	Intermediate Similarity	NPC196227
0.8375	Intermediate Similarity	NPC471514
0.8375	Intermediate Similarity	NPC2482
0.8375	Intermediate Similarity	NPC472301
0.8372	Intermediate Similarity	NPC233116
0.8372	Intermediate Similarity	NPC63748
0.8353	Intermediate Similarity	NPC473999
0.8353	Intermediate Similarity	NPC309603
0.8353	Intermediate Similarity	NPC472973
0.8333	Intermediate Similarity	NPC272039
0.8333	Intermediate Similarity	NPC220930
0.8333	Intermediate Similarity	NPC472305
0.8333	Intermediate Similarity	NPC470525
0.8333	Intermediate Similarity	NPC250621
0.8313	Intermediate Similarity	NPC179006
0.8313	Intermediate Similarity	NPC474853
0.8313	Intermediate Similarity	NPC476426
0.8312	Intermediate Similarity	NPC470299
0.8293	Intermediate Similarity	NPC66764
0.8293	Intermediate Similarity	NPC105173
0.8293	Intermediate Similarity	NPC110150
0.8276	Intermediate Similarity	NPC109305
0.8276	Intermediate Similarity	NPC69454
0.8272	Intermediate Similarity	NPC473420
0.8272	Intermediate Similarity	NPC226068
0.8272	Intermediate Similarity	NPC121984
0.8256	Intermediate Similarity	NPC128672
0.825	Intermediate Similarity	NPC19900
0.825	Intermediate Similarity	NPC229204
0.8235	Intermediate Similarity	NPC471722
0.8214	Intermediate Similarity	NPC158393
0.8214	Intermediate Similarity	NPC198761
0.8214	Intermediate Similarity	NPC72133
0.8214	Intermediate Similarity	NPC322159
0.8205	Intermediate Similarity	NPC114236
0.8202	Intermediate Similarity	NPC117133
0.8193	Intermediate Similarity	NPC227132
0.8193	Intermediate Similarity	NPC476412
0.8193	Intermediate Similarity	NPC470812
0.8193	Intermediate Similarity	NPC472326
0.8182	Intermediate Similarity	NPC474690
0.8182	Intermediate Similarity	NPC472976
0.8182	Intermediate Similarity	NPC186042
0.8182	Intermediate Similarity	NPC472977
0.8171	Intermediate Similarity	NPC38796
0.8171	Intermediate Similarity	NPC158411
0.8161	Intermediate Similarity	NPC473998
0.8161	Intermediate Similarity	NPC472978
0.8161	Intermediate Similarity	NPC73457
0.8161	Intermediate Similarity	NPC475806
0.8158	Intermediate Similarity	NPC173321
0.8148	Intermediate Similarity	NPC271104
0.814	Intermediate Similarity	NPC214387
0.814	Intermediate Similarity	NPC119416
0.814	Intermediate Similarity	NPC472970
0.814	Intermediate Similarity	NPC472971
0.8125	Intermediate Similarity	NPC275494
0.8125	Intermediate Similarity	NPC297996
0.8125	Intermediate Similarity	NPC471409
0.8118	Intermediate Similarity	NPC475740
0.8111	Intermediate Similarity	NPC320306
0.8101	Intermediate Similarity	NPC7629
0.8101	Intermediate Similarity	NPC151622
0.8095	Intermediate Similarity	NPC471224
0.8095	Intermediate Similarity	NPC474083
0.8095	Intermediate Similarity	NPC470574
0.8095	Intermediate Similarity	NPC52628
0.8095	Intermediate Similarity	NPC274724
0.809	Intermediate Similarity	NPC271195
0.809	Intermediate Similarity	NPC476245
0.809	Intermediate Similarity	NPC173875
0.809	Intermediate Similarity	NPC259286
0.809	Intermediate Similarity	NPC174948
0.809	Intermediate Similarity	NPC318282
0.809	Intermediate Similarity	NPC469995
0.8082	Intermediate Similarity	NPC323424
0.8082	Intermediate Similarity	NPC96793
0.8077	Intermediate Similarity	NPC215050
0.8072	Intermediate Similarity	NPC297398
0.8068	Intermediate Similarity	NPC474736
0.8068	Intermediate Similarity	NPC472930
0.8049	Intermediate Similarity	NPC6663
0.8046	Intermediate Similarity	NPC477149
0.8046	Intermediate Similarity	NPC477147
0.8046	Intermediate Similarity	NPC230332
0.8023	Intermediate Similarity	NPC277771
0.8023	Intermediate Similarity	NPC472802
0.8023	Intermediate Similarity	NPC471791
0.8023	Intermediate Similarity	NPC471793
0.8023	Intermediate Similarity	NPC131470
0.8023	Intermediate Similarity	NPC473229
0.8023	Intermediate Similarity	NPC104560
0.8023	Intermediate Similarity	NPC143767
0.8023	Intermediate Similarity	NPC206060
0.8023	Intermediate Similarity	NPC328539
0.8022	Intermediate Similarity	NPC478056
0.8	Intermediate Similarity	NPC179591
0.8	Intermediate Similarity	NPC474732
0.8	Intermediate Similarity	NPC328371
0.8	Intermediate Similarity	NPC94666
0.8	Intermediate Similarity	NPC474778
0.8	Intermediate Similarity	NPC476043
0.8	Intermediate Similarity	NPC471061
0.8	Intermediate Similarity	NPC31564
0.8	Intermediate Similarity	NPC249954
0.8	Intermediate Similarity	NPC474733
0.8	Intermediate Similarity	NPC97377
0.8	Intermediate Similarity	NPC145879
0.7978	Intermediate Similarity	NPC299100
0.7978	Intermediate Similarity	NPC8993
0.7976	Intermediate Similarity	NPC85774
0.7976	Intermediate Similarity	NPC161423
0.7976	Intermediate Similarity	NPC329043
0.7976	Intermediate Similarity	NPC227064
0.7976	Intermediate Similarity	NPC58841
0.7976	Intermediate Similarity	NPC473246
0.7976	Intermediate Similarity	NPC321187
0.7976	Intermediate Similarity	NPC214043
0.7955	Intermediate Similarity	NPC472975
0.7955	Intermediate Similarity	NPC99380
0.7952	Intermediate Similarity	NPC48362
0.7952	Intermediate Similarity	NPC151519
0.7935	Intermediate Similarity	NPC327431
0.7931	Intermediate Similarity	NPC86319
0.7931	Intermediate Similarity	NPC229871
0.7931	Intermediate Similarity	NPC31985
0.7931	Intermediate Similarity	NPC275740
0.7931	Intermediate Similarity	NPC1015
0.7931	Intermediate Similarity	NPC469319
0.7931	Intermediate Similarity	NPC118011
0.7931	Intermediate Similarity	NPC36668
0.7927	Intermediate Similarity	NPC306095
0.7927	Intermediate Similarity	NPC45495
0.7912	Intermediate Similarity	NPC471916
0.7912	Intermediate Similarity	NPC474785
0.7912	Intermediate Similarity	NPC474938
0.7907	Intermediate Similarity	NPC73064
0.7907	Intermediate Similarity	NPC312561
0.7907	Intermediate Similarity	NPC141292
0.7907	Intermediate Similarity	NPC58063
0.7907	Intermediate Similarity	NPC287079
0.7901	Intermediate Similarity	NPC80088
0.7901	Intermediate Similarity	NPC207772
0.7901	Intermediate Similarity	NPC253561
0.7895	Intermediate Similarity	NPC45264
0.7895	Intermediate Similarity	NPC96484
0.7889	Intermediate Similarity	NPC472932
0.7889	Intermediate Similarity	NPC316215
0.7889	Intermediate Similarity	NPC183012
0.7889	Intermediate Similarity	NPC180950
0.7882	Intermediate Similarity	NPC197823
0.7882	Intermediate Similarity	NPC79573
0.7882	Intermediate Similarity	NPC70685
0.7882	Intermediate Similarity	NPC133954
0.7882	Intermediate Similarity	NPC476678
0.7882	Intermediate Similarity	NPC469948
0.7875	Intermediate Similarity	NPC76966
0.7875	Intermediate Similarity	NPC186554
0.7865	Intermediate Similarity	NPC134826
0.7857	Intermediate Similarity	NPC278648
0.7857	Intermediate Similarity	NPC476082
0.7849	Intermediate Similarity	NPC302537

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 NPC281138 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1573
0.2-0.3	3826
0.3-0.4	2427
0.4-0.5	738
0.5-0.6	234
0.6-0.7	183
0.7-0.8	16
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
0.8214	Intermediate Similarity	NPD3618	Phase 1
0.7976	Intermediate Similarity	NPD3666	Approved
0.7976	Intermediate Similarity	NPD3665	Phase 1
0.7976	Intermediate Similarity	NPD3133	Approved
0.7952	Intermediate Similarity	NPD3667	Approved
0.7931	Intermediate Similarity	NPD5328	Approved
0.7765	Intermediate Similarity	NPD4786	Approved
0.7753	Intermediate Similarity	NPD6079	Approved
0.7753	Intermediate Similarity	NPD7515	Phase 2
0.7667	Intermediate Similarity	NPD4202	Approved
0.7586	Intermediate Similarity	NPD5279	Phase 3
0.7586	Intermediate Similarity	NPD4623	Approved
0.7586	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD4695	Discontinued
0.7471	Intermediate Similarity	NPD1694	Approved
0.7419	Intermediate Similarity	NPD5222	Approved
0.7419	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4697	Phase 3
0.7396	Intermediate Similarity	NPD5211	Phase 2
0.7391	Intermediate Similarity	NPD7748	Approved
0.734	Intermediate Similarity	NPD5173	Approved
0.734	Intermediate Similarity	NPD4755	Approved
0.7333	Intermediate Similarity	NPD4753	Phase 2
0.7326	Intermediate Similarity	NPD4223	Phase 3
0.7326	Intermediate Similarity	NPD4221	Approved
0.7294	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1696	Phase 3
0.7262	Intermediate Similarity	NPD3617	Approved
0.7245	Intermediate Similarity	NPD5141	Approved
0.7191	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5286	Approved
0.7188	Intermediate Similarity	NPD5285	Approved
0.7188	Intermediate Similarity	NPD4700	Approved
0.7188	Intermediate Similarity	NPD4696	Approved
0.7159	Intermediate Similarity	NPD4197	Approved
0.7159	Intermediate Similarity	NPD3668	Phase 3
0.7158	Intermediate Similarity	NPD7902	Approved
0.7113	Intermediate Similarity	NPD5223	Approved
0.7079	Intermediate Similarity	NPD5329	Approved
0.7051	Intermediate Similarity	NPD7341	Phase 2
0.7041	Intermediate Similarity	NPD5224	Approved
0.7041	Intermediate Similarity	NPD4633	Approved
0.7041	Intermediate Similarity	NPD5225	Approved
0.7041	Intermediate Similarity	NPD5226	Approved
0.701	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD7640	Approved
0.7	Intermediate Similarity	NPD4138	Approved
0.7	Intermediate Similarity	NPD5205	Approved
0.7	Intermediate Similarity	NPD4688	Approved
0.7	Intermediate Similarity	NPD5690	Phase 2
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD5280	Approved
0.7	Intermediate Similarity	NPD4694	Approved
0.7	Intermediate Similarity	NPD4693	Phase 3
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD4690	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD4689	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.697	Remote Similarity	NPD5175	Approved
0.697	Remote Similarity	NPD5174	Approved
0.697	Remote Similarity	NPD4754	Approved
0.6962	Remote Similarity	NPD7331	Phase 2
0.6947	Remote Similarity	NPD5210	Approved
0.6947	Remote Similarity	NPD4629	Approved
0.6915	Remote Similarity	NPD5778	Approved
0.6915	Remote Similarity	NPD6399	Phase 3
0.6915	Remote Similarity	NPD5779	Approved
0.6907	Remote Similarity	NPD7638	Approved
0.6907	Remote Similarity	NPD4225	Approved
0.6905	Remote Similarity	NPD8264	Approved
0.6889	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD368	Approved
0.686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4788	Approved
0.6848	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6903	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7900	Approved
0.6832	Remote Similarity	NPD4768	Approved
0.6832	Remote Similarity	NPD5739	Approved
0.6832	Remote Similarity	NPD6675	Approved
0.6832	Remote Similarity	NPD4767	Approved
0.6832	Remote Similarity	NPD6402	Approved
0.6832	Remote Similarity	NPD7128	Approved
0.6824	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7115	Discovery
0.6809	Remote Similarity	NPD6411	Approved
0.6804	Remote Similarity	NPD6084	Phase 2
0.6804	Remote Similarity	NPD6083	Phase 2
0.6782	Remote Similarity	NPD7645	Phase 2
0.6774	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5695	Phase 3
0.6765	Remote Similarity	NPD5701	Approved
0.6765	Remote Similarity	NPD5697	Approved
0.6757	Remote Similarity	NPD342	Phase 1
0.6742	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3573	Approved
0.6707	Remote Similarity	NPD4137	Phase 3
0.6706	Remote Similarity	NPD7339	Approved
0.6706	Remote Similarity	NPD6942	Approved
0.6703	Remote Similarity	NPD5363	Approved
0.6702	Remote Similarity	NPD5785	Approved
0.6699	Remote Similarity	NPD7320	Approved
0.6699	Remote Similarity	NPD5168	Approved
0.6699	Remote Similarity	NPD6881	Approved
0.6699	Remote Similarity	NPD4730	Approved
0.6699	Remote Similarity	NPD6899	Approved
0.6699	Remote Similarity	NPD6011	Approved
0.6699	Remote Similarity	NPD4729	Approved
0.6699	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6635	Remote Similarity	NPD6013	Approved
0.6635	Remote Similarity	NPD6012	Approved
0.6635	Remote Similarity	NPD6014	Approved
0.6635	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD6372	Approved
0.6632	Remote Similarity	NPD5284	Approved
0.6632	Remote Similarity	NPD5281	Approved
0.6629	Remote Similarity	NPD4139	Approved
0.6629	Remote Similarity	NPD4692	Approved
0.6627	Remote Similarity	NPD4747	Approved
0.6627	Remote Similarity	NPD4691	Approved
0.6596	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6101	Approved
0.6591	Remote Similarity	NPD6929	Approved
0.6591	Remote Similarity	NPD4195	Approved
0.6588	Remote Similarity	NPD6926	Approved
0.6588	Remote Similarity	NPD6924	Approved
0.6571	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD5250	Approved
0.6571	Remote Similarity	NPD5169	Approved
0.6571	Remote Similarity	NPD7290	Approved
0.6571	Remote Similarity	NPD7102	Approved
0.6571	Remote Similarity	NPD5248	Approved
0.6571	Remote Similarity	NPD5251	Approved
0.6571	Remote Similarity	NPD5247	Approved
0.6571	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5249	Phase 3
0.6571	Remote Similarity	NPD5135	Approved
0.6571	Remote Similarity	NPD6883	Approved
0.6566	Remote Similarity	NPD5696	Approved
0.6559	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4270	Approved
0.6556	Remote Similarity	NPD4269	Approved
0.6543	Remote Similarity	NPD3704	Approved
0.6535	Remote Similarity	NPD7632	Discontinued
0.6526	Remote Similarity	NPD4096	Approved
0.6517	Remote Similarity	NPD6931	Approved
0.6517	Remote Similarity	NPD6930	Phase 2
0.6517	Remote Similarity	NPD7525	Registered
0.6509	Remote Similarity	NPD6617	Approved
0.6509	Remote Similarity	NPD6649	Approved
0.6509	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD6650	Approved
0.6509	Remote Similarity	NPD8130	Phase 1
0.6509	Remote Similarity	NPD6869	Approved
0.6509	Remote Similarity	NPD5127	Approved
0.6509	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5216	Approved
0.6509	Remote Similarity	NPD5215	Approved
0.6509	Remote Similarity	NPD5217	Approved
0.6506	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5362	Discontinued
0.6484	Remote Similarity	NPD7154	Phase 3
0.6477	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6882	Approved
0.6449	Remote Similarity	NPD8297	Approved
0.6442	Remote Similarity	NPD6412	Phase 2
0.6437	Remote Similarity	NPD6933	Approved
0.6429	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5290	Discontinued
0.6395	Remote Similarity	NPD4687	Approved
0.6395	Remote Similarity	NPD4058	Approved
0.6395	Remote Similarity	NPD5733	Approved
0.6392	Remote Similarity	NPD5133	Approved
0.6389	Remote Similarity	NPD4632	Approved
0.6375	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4756	Discovery
0.6364	Remote Similarity	NPD6925	Approved
0.6364	Remote Similarity	NPD5776	Phase 2
0.6354	Remote Similarity	NPD46	Approved
0.6354	Remote Similarity	NPD6698	Approved
0.6353	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5276	Approved
0.6353	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6008	Approved
0.6337	Remote Similarity	NPD6404	Discontinued
0.6333	Remote Similarity	NPD4252	Approved
0.6333	Remote Similarity	NPD7509	Discontinued

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