NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.2
Volume:	257.037
LogP:	4.259
LogD:	3.573
LogS:	-2.658
# 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:	0.667
Synthetic Accessibility Score:	4.574
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.447
MDCK Permeability:	1.420393255102681e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.351

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	94.90094757080078%
Volume Distribution (VD):	1.127
Pgp-substrate:	4.5183186531066895%

ADMET: Metabolism

CYP1A2-inhibitor:	0.194
CYP1A2-substrate:	0.348
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.901
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.47
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.273
CYP3A4-inhibitor:	0.32
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	10.72
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.432
Skin Sensitization:	0.907
Carcinogencity:	0.294
Eye Corrosion:	0.945
Eye Irritation:	0.951
Respiratory Toxicity:	0.883

Download Data

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

Natural Product: NPC135648

Natural Product ID:	NPC135648
*Common Name:**	Hinesol
IUPAC Name:	2-[(3R,5S,6S)-6,10-dimethylspiro[4.5]dec-9-en-3-yl]propan-2-ol
Synonyms:	Hinesol
Standard InCHIKey:	ICWHTQRTTHCUHW-GZBFAFLISA-N
Standard InCHI:	InChI=1S/C15H26O/c1-11-6-5-7-12(2)15(11)9-8-13(10-15)14(3,4)16/h6,12-13,16H,5,7-10H2,1-4H3/t12-,13+,15+/m0/s1
SMILES:	C[C@H]1CCC=C([C@@]21CC[C@H](C2)C(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505813
PubChem CID:	10878761
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] 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
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15467238]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787437]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378364]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17432574]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27128895]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	Resinous Wood	n.a.	n.a.	PMID[29227647]
NPO40789	Atractylodes rhizomes	Species	Asteraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[6418860]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3083	Ferula assafoetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[p25172756]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3083	Ferula assafoetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3083	Ferula assafoetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3412	Ferula sinkiangensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19649	Akebia quinata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12265	Aquilaria agallochum	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11170	Akebia trifoliata	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20902	Atractylodes macrocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14558	Aquilaria sinensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12584	Atractylodes chinensis	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
LD50	1
Others	7

Activity Type	# Activity
Cell Line	6
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	73.0	%	PMID[502436]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	99.0	%	PMID[502436]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	101.0	%	PMID[502436]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	31.0	%	PMID[502436]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	62.0	%	PMID[502436]
NPT1135	Cell Line	Hepatocyte	Rattus norvegicus	Activity	=	79.0	%	PMID[502436]
NPT2967	Individual Protein	Alanine aminotransferase	Rattus norvegicus	Activity	=	105.0	%	PMID[502436]
NPT1077	Organism	Drosophila melanogaster	Drosophila melanogaster	LD50	=	0.71	ug	PMID[502437]

☑ 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 NPC135648 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	134
0.1-0.2	2004
0.2-0.3	14904
0.3-0.4	12186
0.4-0.5	7727
0.5-0.6	4485
0.6-0.7	1087
0.7-0.8	151
0.8-0.85	14
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8814	High Similarity	NPC5698
0.8667	High Similarity	NPC323153
0.8615	High Similarity	NPC475728
0.8475	Intermediate Similarity	NPC278550
0.8387	Intermediate Similarity	NPC81615
0.8361	Intermediate Similarity	NPC252809
0.8305	Intermediate Similarity	NPC179024
0.8305	Intermediate Similarity	NPC39068
0.8281	Intermediate Similarity	NPC279434
0.8246	Intermediate Similarity	NPC181255
0.8246	Intermediate Similarity	NPC35519
0.8246	Intermediate Similarity	NPC306195
0.8246	Intermediate Similarity	NPC157781
0.8246	Intermediate Similarity	NPC179169
0.8226	Intermediate Similarity	NPC79576
0.8226	Intermediate Similarity	NPC194208
0.8226	Intermediate Similarity	NPC282694
0.8095	Intermediate Similarity	NPC174956
0.8095	Intermediate Similarity	NPC474480
0.8088	Intermediate Similarity	NPC474140
0.807	Intermediate Similarity	NPC214584
0.807	Intermediate Similarity	NPC26906
0.803	Intermediate Similarity	NPC160209
0.8	Intermediate Similarity	NPC264779
0.7969	Intermediate Similarity	NPC290367
0.7969	Intermediate Similarity	NPC309300
0.7937	Intermediate Similarity	NPC63111
0.7937	Intermediate Similarity	NPC210346
0.7903	Intermediate Similarity	NPC469321
0.7887	Intermediate Similarity	NPC155986
0.7887	Intermediate Similarity	NPC318495
0.7887	Intermediate Similarity	NPC198968
0.7879	Intermediate Similarity	NPC136813
0.7857	Intermediate Similarity	NPC288035
0.7857	Intermediate Similarity	NPC471723
0.7857	Intermediate Similarity	NPC136188
0.7857	Intermediate Similarity	NPC162742
0.7857	Intermediate Similarity	NPC141071
0.7857	Intermediate Similarity	NPC257347
0.7857	Intermediate Similarity	NPC304309
0.7857	Intermediate Similarity	NPC22105
0.7857	Intermediate Similarity	NPC230301
0.7857	Intermediate Similarity	NPC285893
0.7857	Intermediate Similarity	NPC28657
0.7857	Intermediate Similarity	NPC134847
0.7846	Intermediate Similarity	NPC238352
0.7846	Intermediate Similarity	NPC477009
0.7833	Intermediate Similarity	NPC218525
0.7761	Intermediate Similarity	NPC208999
0.7761	Intermediate Similarity	NPC94192
0.7746	Intermediate Similarity	NPC107059
0.7746	Intermediate Similarity	NPC129165
0.7746	Intermediate Similarity	NPC134330
0.7746	Intermediate Similarity	NPC244488
0.7746	Intermediate Similarity	NPC321016
0.7746	Intermediate Similarity	NPC46160
0.7746	Intermediate Similarity	NPC470362
0.7746	Intermediate Similarity	NPC202642
0.7746	Intermediate Similarity	NPC189883
0.7746	Intermediate Similarity	NPC113733
0.7746	Intermediate Similarity	NPC300324
0.7746	Intermediate Similarity	NPC321381
0.7746	Intermediate Similarity	NPC240604
0.7746	Intermediate Similarity	NPC247325
0.7742	Intermediate Similarity	NPC474769
0.7742	Intermediate Similarity	NPC189290
0.7714	Intermediate Similarity	NPC329090
0.7714	Intermediate Similarity	NPC309178
0.7714	Intermediate Similarity	NPC27395
0.7705	Intermediate Similarity	NPC274396
0.7692	Intermediate Similarity	NPC225415
0.7692	Intermediate Similarity	NPC219940
0.7692	Intermediate Similarity	NPC107540
0.7681	Intermediate Similarity	NPC164022
0.7671	Intermediate Similarity	NPC328714
0.7656	Intermediate Similarity	NPC41160
0.7656	Intermediate Similarity	NPC147524
0.7656	Intermediate Similarity	NPC475251
0.7647	Intermediate Similarity	NPC474248
0.7647	Intermediate Similarity	NPC476431
0.7647	Intermediate Similarity	NPC473893
0.7639	Intermediate Similarity	NPC214570
0.7639	Intermediate Similarity	NPC34019
0.7627	Intermediate Similarity	NPC71506
0.7627	Intermediate Similarity	NPC177112
0.7619	Intermediate Similarity	NPC99480
0.7619	Intermediate Similarity	NPC184049
0.7612	Intermediate Similarity	NPC197805
0.7612	Intermediate Similarity	NPC114651
0.7612	Intermediate Similarity	NPC171225
0.7606	Intermediate Similarity	NPC322353
0.7606	Intermediate Similarity	NPC118508
0.7606	Intermediate Similarity	NPC319090
0.7606	Intermediate Similarity	NPC121744
0.7606	Intermediate Similarity	NPC328104
0.7606	Intermediate Similarity	NPC471468
0.7586	Intermediate Similarity	NPC329773
0.7576	Intermediate Similarity	NPC261782
0.7576	Intermediate Similarity	NPC469326
0.7576	Intermediate Similarity	NPC205618
0.7568	Intermediate Similarity	NPC209944
0.7568	Intermediate Similarity	NPC241290
0.7568	Intermediate Similarity	NPC164840
0.7536	Intermediate Similarity	NPC145498
0.7536	Intermediate Similarity	NPC92801
0.7536	Intermediate Similarity	NPC34834
0.7534	Intermediate Similarity	NPC18603
0.7534	Intermediate Similarity	NPC307965
0.7534	Intermediate Similarity	NPC477514
0.7534	Intermediate Similarity	NPC474216
0.7534	Intermediate Similarity	NPC473943
0.7534	Intermediate Similarity	NPC76931
0.7534	Intermediate Similarity	NPC477522
0.7534	Intermediate Similarity	NPC205455
0.7534	Intermediate Similarity	NPC87604
0.7534	Intermediate Similarity	NPC275910
0.7534	Intermediate Similarity	NPC285761
0.7534	Intermediate Similarity	NPC186191
0.75	Intermediate Similarity	NPC73875
0.75	Intermediate Similarity	NPC66020
0.75	Intermediate Similarity	NPC216460
0.75	Intermediate Similarity	NPC192962
0.75	Intermediate Similarity	NPC96319
0.75	Intermediate Similarity	NPC167527
0.75	Intermediate Similarity	NPC237460
0.75	Intermediate Similarity	NPC315261
0.75	Intermediate Similarity	NPC96484
0.7467	Intermediate Similarity	NPC264245
0.7467	Intermediate Similarity	NPC47761
0.7465	Intermediate Similarity	NPC469534
0.7465	Intermediate Similarity	NPC469533
0.7465	Intermediate Similarity	NPC469593
0.7463	Intermediate Similarity	NPC162309
0.7463	Intermediate Similarity	NPC149680
0.7463	Intermediate Similarity	NPC286669
0.7463	Intermediate Similarity	NPC222366
0.7463	Intermediate Similarity	NPC202017
0.7463	Intermediate Similarity	NPC327815
0.7463	Intermediate Similarity	NPC476039
0.746	Intermediate Similarity	NPC10017
0.7432	Intermediate Similarity	NPC143182
0.7432	Intermediate Similarity	NPC81306
0.7432	Intermediate Similarity	NPC215843
0.7432	Intermediate Similarity	NPC84694
0.7432	Intermediate Similarity	NPC30986
0.7432	Intermediate Similarity	NPC80530
0.7432	Intermediate Similarity	NPC209430
0.7432	Intermediate Similarity	NPC109546
0.7432	Intermediate Similarity	NPC28862
0.7432	Intermediate Similarity	NPC1319
0.7432	Intermediate Similarity	NPC47982
0.7432	Intermediate Similarity	NPC273410
0.7432	Intermediate Similarity	NPC477371
0.7429	Intermediate Similarity	NPC167706
0.7429	Intermediate Similarity	NPC242001
0.7429	Intermediate Similarity	NPC471660
0.7429	Intermediate Similarity	NPC469343
0.7424	Intermediate Similarity	NPC287744
0.7424	Intermediate Similarity	NPC140233
0.7391	Intermediate Similarity	NPC167272
0.7391	Intermediate Similarity	NPC269877
0.7391	Intermediate Similarity	NPC471560
0.7385	Intermediate Similarity	NPC15152
0.7368	Intermediate Similarity	NPC30166
0.7368	Intermediate Similarity	NPC193347
0.7368	Intermediate Similarity	NPC87489
0.7368	Intermediate Similarity	NPC49964
0.7361	Intermediate Similarity	NPC313185
0.7353	Intermediate Similarity	NPC477791
0.7353	Intermediate Similarity	NPC68703
0.7353	Intermediate Similarity	NPC69649
0.7353	Intermediate Similarity	NPC74885
0.7353	Intermediate Similarity	NPC308522
0.7344	Intermediate Similarity	NPC309825
0.7333	Intermediate Similarity	NPC13554
0.7333	Intermediate Similarity	NPC234193
0.7333	Intermediate Similarity	NPC236237
0.7333	Intermediate Similarity	NPC26117
0.7333	Intermediate Similarity	NPC102253
0.7333	Intermediate Similarity	NPC322313
0.7333	Intermediate Similarity	NPC236112
0.7324	Intermediate Similarity	NPC201373
0.7324	Intermediate Similarity	NPC182717
0.7324	Intermediate Similarity	NPC471799
0.7313	Intermediate Similarity	NPC27243
0.7313	Intermediate Similarity	NPC300442
0.7313	Intermediate Similarity	NPC476737
0.7313	Intermediate Similarity	NPC64123
0.7313	Intermediate Similarity	NPC19569
0.7313	Intermediate Similarity	NPC471200
0.7313	Intermediate Similarity	NPC163678
0.7297	Intermediate Similarity	NPC138621
0.7297	Intermediate Similarity	NPC244385
0.7297	Intermediate Similarity	NPC167037
0.7297	Intermediate Similarity	NPC65897
0.7297	Intermediate Similarity	NPC302041
0.7297	Intermediate Similarity	NPC6978
0.7297	Intermediate Similarity	NPC318136
0.7297	Intermediate Similarity	NPC85346
0.7286	Intermediate Similarity	NPC9161

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 NPC135648 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	2608
0.2-0.3	4329
0.3-0.4	1474
0.4-0.5	321
0.5-0.6	201
0.6-0.7	67
0.7-0.8	13
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
0.8485	Intermediate Similarity	NPD4243	Approved
0.8235	Intermediate Similarity	NPD4784	Approved
0.8235	Intermediate Similarity	NPD4785	Approved
0.8116	Intermediate Similarity	NPD4190	Phase 3
0.8116	Intermediate Similarity	NPD5275	Approved
0.7857	Intermediate Similarity	NPD6942	Approved
0.7857	Intermediate Similarity	NPD7339	Approved
0.7714	Intermediate Similarity	NPD6926	Approved
0.7714	Intermediate Similarity	NPD6924	Approved
0.7671	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6933	Approved
0.7391	Intermediate Similarity	NPD6923	Approved
0.7391	Intermediate Similarity	NPD6922	Approved
0.7368	Intermediate Similarity	NPD4223	Phase 3
0.7368	Intermediate Similarity	NPD4221	Approved
0.7333	Intermediate Similarity	NPD7525	Registered
0.7286	Intermediate Similarity	NPD7143	Approved
0.7286	Intermediate Similarity	NPD7144	Approved
0.7183	Intermediate Similarity	NPD7151	Approved
0.7183	Intermediate Similarity	NPD7150	Approved
0.7183	Intermediate Similarity	NPD7152	Approved
0.7179	Intermediate Similarity	NPD4197	Approved
0.7105	Intermediate Similarity	NPD6931	Approved
0.7105	Intermediate Similarity	NPD6930	Phase 2
0.7089	Intermediate Similarity	NPD5329	Approved
0.7027	Intermediate Similarity	NPD1346	Approved
0.7	Intermediate Similarity	NPD4138	Approved
0.7	Intermediate Similarity	NPD4694	Approved
0.7	Intermediate Similarity	NPD5205	Approved
0.7	Intermediate Similarity	NPD5280	Approved
0.7	Intermediate Similarity	NPD4688	Approved
0.7	Intermediate Similarity	NPD4693	Phase 3
0.7	Intermediate Similarity	NPD4690	Approved
0.7	Intermediate Similarity	NPD5690	Phase 2
0.7	Intermediate Similarity	NPD4689	Approved
0.6984	Remote Similarity	NPD342	Phase 1
0.6974	Remote Similarity	NPD6929	Approved
0.6962	Remote Similarity	NPD4786	Approved
0.6933	Remote Similarity	NPD6932	Approved
0.6923	Remote Similarity	NPD3667	Approved
0.6914	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4748	Discontinued
0.6883	Remote Similarity	NPD7509	Discontinued
0.6866	Remote Similarity	NPD368	Approved
0.6835	Remote Similarity	NPD6695	Phase 3
0.6829	Remote Similarity	NPD4722	Approved
0.6829	Remote Similarity	NPD4723	Approved
0.6795	Remote Similarity	NPD4139	Approved
0.6795	Remote Similarity	NPD4692	Approved
0.679	Remote Similarity	NPD5279	Phase 3
0.6753	Remote Similarity	NPD7645	Phase 2
0.6753	Remote Similarity	NPD6683	Phase 2
0.675	Remote Similarity	NPD3133	Approved
0.675	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3665	Phase 1
0.675	Remote Similarity	NPD3666	Approved
0.6747	Remote Similarity	NPD4753	Phase 2
0.6711	Remote Similarity	NPD5776	Phase 2
0.6711	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD4096	Approved
0.6627	Remote Similarity	NPD4518	Approved
0.6623	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7145	Approved
0.6623	Remote Similarity	NPD3617	Approved
0.6588	Remote Similarity	NPD5281	Approved
0.6588	Remote Similarity	NPD5284	Approved
0.6585	Remote Similarity	NPD3618	Phase 1
0.6585	Remote Similarity	NPD4519	Discontinued
0.6585	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4623	Approved
0.6548	Remote Similarity	NPD5328	Approved
0.6512	Remote Similarity	NPD4202	Approved
0.6506	Remote Similarity	NPD7524	Approved
0.6506	Remote Similarity	NPD7750	Discontinued
0.6479	Remote Similarity	NPD7331	Phase 2
0.6471	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD7332	Phase 2
0.6395	Remote Similarity	NPD6079	Approved
0.6386	Remote Similarity	NPD6098	Approved
0.6375	Remote Similarity	NPD6902	Approved
0.6375	Remote Similarity	NPD6898	Phase 1
0.6364	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD4629	Approved
0.6364	Remote Similarity	NPD4219	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6351	Remote Similarity	NPD4747	Approved
0.6341	Remote Similarity	NPD3668	Phase 3
0.6338	Remote Similarity	NPD7341	Phase 2
0.6322	Remote Similarity	NPD5133	Approved
0.6322	Remote Similarity	NPD6399	Phase 3
0.6301	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD5276	Approved
0.6235	Remote Similarity	NPD5208	Approved
0.6222	Remote Similarity	NPD4755	Approved
0.6222	Remote Similarity	NPD6083	Phase 2
0.6222	Remote Similarity	NPD6084	Phase 2
0.622	Remote Similarity	NPD4788	Approved
0.6216	Remote Similarity	NPD4137	Phase 3
0.6216	Remote Similarity	NPD791	Approved
0.6216	Remote Similarity	NPD15	Approved
0.6207	Remote Similarity	NPD7087	Discontinued
0.6176	Remote Similarity	NPD287	Approved
0.6163	Remote Similarity	NPD6051	Approved
0.6163	Remote Similarity	NPD6904	Approved
0.6163	Remote Similarity	NPD6080	Approved
0.6163	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6133	Remote Similarity	NPD4691	Approved
0.6111	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4697	Phase 3
0.6111	Remote Similarity	NPD5222	Approved
0.6111	Remote Similarity	NPD5221	Approved
0.6104	Remote Similarity	NPD5733	Approved
0.6104	Remote Similarity	NPD4687	Approved
0.6102	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD5207	Approved
0.6092	Remote Similarity	NPD5692	Phase 3
0.6087	Remote Similarity	NPD4696	Approved
0.6087	Remote Similarity	NPD4700	Approved
0.6087	Remote Similarity	NPD5285	Approved
0.6087	Remote Similarity	NPD5286	Approved
0.6071	Remote Similarity	NPD1696	Phase 3
0.6067	Remote Similarity	NPD5707	Approved
0.6047	Remote Similarity	NPD6672	Approved
0.6047	Remote Similarity	NPD5737	Approved
0.6044	Remote Similarity	NPD5173	Approved
0.6023	Remote Similarity	NPD6050	Approved
0.6023	Remote Similarity	NPD5693	Phase 1
0.6023	Remote Similarity	NPD5694	Approved
0.6022	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD1082	Approved
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.5976	Remote Similarity	NPD857	Phase 3
0.5957	Remote Similarity	NPD5091	Approved
0.5957	Remote Similarity	NPD5225	Approved
0.5957	Remote Similarity	NPD5211	Phase 2
0.5957	Remote Similarity	NPD5224	Approved
0.5957	Remote Similarity	NPD5226	Approved
0.5957	Remote Similarity	NPD4633	Approved
0.5921	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD6939	Phase 2
0.5915	Remote Similarity	NPD4194	Approved
0.5915	Remote Similarity	NPD4192	Approved
0.5915	Remote Similarity	NPD4193	Approved
0.5915	Remote Similarity	NPD4191	Approved
0.5897	Remote Similarity	NPD4058	Approved
0.5895	Remote Similarity	NPD5174	Approved
0.5895	Remote Similarity	NPD4754	Approved
0.5895	Remote Similarity	NPD5175	Approved
0.5889	Remote Similarity	NPD6001	Approved
0.5882	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6903	Approved
0.5843	Remote Similarity	NPD7515	Phase 2
0.5833	Remote Similarity	NPD5141	Approved
0.5824	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5290	Discontinued
0.5806	Remote Similarity	NPD388	Approved
0.5806	Remote Similarity	NPD386	Approved
0.5795	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD319	Phase 1
0.5781	Remote Similarity	NPD8262	Approved
0.5775	Remote Similarity	NPD1145	Discontinued
0.5773	Remote Similarity	NPD7128	Approved
0.5773	Remote Similarity	NPD6402	Approved
0.5773	Remote Similarity	NPD6675	Approved
0.5773	Remote Similarity	NPD4767	Approved
0.5773	Remote Similarity	NPD5739	Approved
0.5773	Remote Similarity	NPD4768	Approved
0.5747	Remote Similarity	NPD3573	Approved
0.5745	Remote Similarity	NPD6404	Discontinued
0.5714	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD5701	Approved
0.5676	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7637	Suspended
0.5667	Remote Similarity	NPD6411	Approved
0.5663	Remote Similarity	NPD4819	Approved
0.5663	Remote Similarity	NPD4820	Approved
0.5663	Remote Similarity	NPD4822	Approved
0.5663	Remote Similarity	NPD4821	Approved
0.5658	Remote Similarity	NPD5360	Phase 3
0.5658	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD7320	Approved
0.5657	Remote Similarity	NPD4730	Approved
0.5657	Remote Similarity	NPD6899	Approved
0.5657	Remote Similarity	NPD6011	Approved
0.5657	Remote Similarity	NPD6881	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