NPASS Compound

Structure

CID267539 OpenBabel06191716072D 28 28 0 0 1 0 0 0 0 0999 V2000 -8.6603 -13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -13.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 20 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 16 1 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 28 1 0 0 0 0 20 2 1 1 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.29
Volume:	439.719
LogP:	8.377
LogD:	4.384
LogS:	-4.314
# Rotatable Bonds:	17
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	2.659
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.877
MDCK Permeability:	1.558440999360755e-05
Pgp-inhibitor:	0.461
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	99.82032012939453%
Volume Distribution (VD):	4.773
Pgp-substrate:	1.0601155757904053%

ADMET: Metabolism

CYP1A2-inhibitor:	0.342
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.63
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.664
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.246
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	7.797
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.006
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.962
Carcinogencity:	0.126
Eye Corrosion:	0.542
Eye Irritation:	0.95
Respiratory Toxicity:	0.616

Download Data

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

Natural Product: NPC267539

Natural Product ID:	NPC267539
*Common Name:**	Gentiside C
IUPAC Name:	[(14S)-14-methylhexadecyl] 2,3-dihydroxybenzoate
Synonyms:	Gentiside C
Standard InCHIKey:	XGXUFBAHOWHDNU-FQEVSTJZSA-N
Standard InCHI:	InChI=1S/C24H40O4/c1-3-20(2)16-13-11-9-7-5-4-6-8-10-12-14-19-28-24(27)21-17-15-18-22(25)23(21)26/h15,17-18,20,25-26H,3-14,16,19H2,1-2H3/t20-/m0/s1
SMILES:	CC[C@@H](CCCCCCCCCCCCCOC(=O)c1cccc(c1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1254184
PubChem CID:	46899083
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004699] m-Hydroxybenzoic acid esters

*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
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	roots	n.a.	n.a.	PMID[17375953]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20813533]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21043460]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21043460]
NPO27624	Swartzia simplex	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26654828]
NPO12009	Abies pinsapo	Species	Pinaceae	Eukaryota	Wood	n.a.	n.a.	PMID[7931362]
NPO16073	Sarcomelicope megistophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19120	Strychnos aculeata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15856	Podocarpus hallii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17368	Erythrina senegalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18843	Antirrhinum majus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16073	Sarcomelicope megistophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18843	Antirrhinum majus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19120	Strychnos aculeata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15856	Podocarpus hallii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16817	Aglaia argentea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17368	Erythrina senegalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15856	Podocarpus hallii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18843	Antirrhinum majus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18234	Gentiana rigescens	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18372	Lobophytum crassospiculatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15518	Streptomyces netropsis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18843	Antirrhinum majus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16817	Aglaia argentea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13251	Iris nertchinskia	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12009	Abies pinsapo	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19120	Strychnos aculeata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15856	Podocarpus hallii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17368	Erythrina senegalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18511	Latimeria chalumnae	Species	Coelacanthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27624	Swartzia simplex	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14721	Dentitheca habereri	Species	Plumulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17711	Sphenoclea zeylanica	Species	Sphenocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16073	Sarcomelicope megistophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17493	Alstonia spatulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16646	Artemisia campestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17699	Solanum glaucophyllum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3046	Schisandra bicolor	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16958	Jurinea albicaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17054	Streptomyces gardneri	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18234	Gentiana rigescens	Species	Gentianaceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	67.0	%	PMID[521176]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	91.0	%	PMID[521176]

☑ 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 NPC267539 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	286
0.1-0.2	1210
0.2-0.3	3182
0.3-0.4	7548
0.4-0.5	11060
0.5-0.6	4249
0.6-0.7	8404
0.7-0.8	6471
0.8-0.85	255
0.85-0.9	21
0.9-0.95	0
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC29317
1.0	High Similarity	NPC254832
1.0	High Similarity	NPC204257
1.0	High Similarity	NPC229638
1.0	High Similarity	NPC71108
1.0	High Similarity	NPC176102
0.9844	High Similarity	NPC295406
0.9844	High Similarity	NPC289572
0.9844	High Similarity	NPC200422
0.9844	High Similarity	NPC157478
0.8815	High Similarity	NPC472591
0.8806	High Similarity	NPC7012
0.875	High Similarity	NPC260837
0.875	High Similarity	NPC72977
0.8681	High Similarity	NPC55327
0.8672	High Similarity	NPC328459
0.8672	High Similarity	NPC90522
0.8623	High Similarity	NPC156892
0.8594	High Similarity	NPC94637
0.8561	High Similarity	NPC62907
0.8551	High Similarity	NPC18646
0.854	High Similarity	NPC239855
0.854	High Similarity	NPC43627
0.8519	High Similarity	NPC226855
0.8507	High Similarity	NPC71525
0.85	High Similarity	NPC112135
0.8496	Intermediate Similarity	NPC167055
0.8496	Intermediate Similarity	NPC240744
0.8489	Intermediate Similarity	NPC475111
0.8485	Intermediate Similarity	NPC477153
0.8478	Intermediate Similarity	NPC106406
0.8478	Intermediate Similarity	NPC474097
0.8467	Intermediate Similarity	NPC470160
0.8451	Intermediate Similarity	NPC130485
0.844	Intermediate Similarity	NPC471819
0.8438	Intermediate Similarity	NPC128825
0.8421	Intermediate Similarity	NPC117794
0.8414	Intermediate Similarity	NPC32058
0.8414	Intermediate Similarity	NPC85734
0.8406	Intermediate Similarity	NPC304929
0.8406	Intermediate Similarity	NPC1321
0.8406	Intermediate Similarity	NPC156124
0.8397	Intermediate Similarity	NPC301987
0.8397	Intermediate Similarity	NPC159760
0.8397	Intermediate Similarity	NPC115188
0.8397	Intermediate Similarity	NPC35856
0.8397	Intermediate Similarity	NPC26433
0.8397	Intermediate Similarity	NPC292665
0.8397	Intermediate Similarity	NPC244994
0.8397	Intermediate Similarity	NPC222876
0.8397	Intermediate Similarity	NPC178395
0.8397	Intermediate Similarity	NPC179092
0.8397	Intermediate Similarity	NPC272454
0.8389	Intermediate Similarity	NPC472127
0.8389	Intermediate Similarity	NPC472128
0.8382	Intermediate Similarity	NPC261759
0.837	Intermediate Similarity	NPC158654
0.8369	Intermediate Similarity	NPC126739
0.8369	Intermediate Similarity	NPC197666
0.8358	Intermediate Similarity	NPC472592
0.8358	Intermediate Similarity	NPC287473
0.8345	Intermediate Similarity	NPC204582
0.8345	Intermediate Similarity	NPC83272
0.8333	Intermediate Similarity	NPC25168
0.8333	Intermediate Similarity	NPC469615
0.8333	Intermediate Similarity	NPC258307
0.8322	Intermediate Similarity	NPC199773
0.8321	Intermediate Similarity	NPC233282
0.831	Intermediate Similarity	NPC134969
0.8308	Intermediate Similarity	NPC203124
0.8298	Intermediate Similarity	NPC279676
0.8298	Intermediate Similarity	NPC67349
0.8298	Intermediate Similarity	NPC71256
0.8288	Intermediate Similarity	NPC229264
0.8286	Intermediate Similarity	NPC27407
0.8286	Intermediate Similarity	NPC142027
0.8284	Intermediate Similarity	NPC469568
0.8284	Intermediate Similarity	NPC91475
0.8284	Intermediate Similarity	NPC265910
0.8281	Intermediate Similarity	NPC81808
0.8276	Intermediate Similarity	NPC469683
0.8276	Intermediate Similarity	NPC103910
0.8273	Intermediate Similarity	NPC475468
0.8271	Intermediate Similarity	NPC132518
0.8271	Intermediate Similarity	NPC327070
0.8271	Intermediate Similarity	NPC477151
0.8271	Intermediate Similarity	NPC325301
0.8264	Intermediate Similarity	NPC314271
0.8261	Intermediate Similarity	NPC264145
0.8258	Intermediate Similarity	NPC165197
0.8252	Intermediate Similarity	NPC327916
0.8252	Intermediate Similarity	NPC42262
0.8252	Intermediate Similarity	NPC147542
0.8252	Intermediate Similarity	NPC37992
0.8252	Intermediate Similarity	NPC158472
0.8252	Intermediate Similarity	NPC241349
0.8252	Intermediate Similarity	NPC220496
0.8252	Intermediate Similarity	NPC32749
0.8244	Intermediate Similarity	NPC233165
0.8244	Intermediate Similarity	NPC184579
0.8231	Intermediate Similarity	NPC113428
0.8231	Intermediate Similarity	NPC61284
0.8231	Intermediate Similarity	NPC160199
0.8231	Intermediate Similarity	NPC28169
0.8231	Intermediate Similarity	NPC476463
0.8227	Intermediate Similarity	NPC90431
0.8222	Intermediate Similarity	NPC4164
0.8219	Intermediate Similarity	NPC258856
0.8219	Intermediate Similarity	NPC75295
0.8214	Intermediate Similarity	NPC471110
0.8212	Intermediate Similarity	NPC79998
0.8212	Intermediate Similarity	NPC82592
0.8212	Intermediate Similarity	NPC16082
0.8207	Intermediate Similarity	NPC183824
0.82	Intermediate Similarity	NPC295646
0.8194	Intermediate Similarity	NPC257003
0.8194	Intermediate Similarity	NPC471444
0.8188	Intermediate Similarity	NPC31132
0.8188	Intermediate Similarity	NPC56204
0.8182	Intermediate Similarity	NPC476477
0.8182	Intermediate Similarity	NPC306835
0.8182	Intermediate Similarity	NPC256463
0.8182	Intermediate Similarity	NPC179505
0.8182	Intermediate Similarity	NPC471602
0.8182	Intermediate Similarity	NPC216312
0.8182	Intermediate Similarity	NPC295339
0.8182	Intermediate Similarity	NPC111422
0.8182	Intermediate Similarity	NPC299405
0.8182	Intermediate Similarity	NPC156709
0.8182	Intermediate Similarity	NPC29771
0.8169	Intermediate Similarity	NPC70380
0.8169	Intermediate Similarity	NPC308976
0.8168	Intermediate Similarity	NPC309434
0.8163	Intermediate Similarity	NPC308799
0.8158	Intermediate Similarity	NPC150227
0.8158	Intermediate Similarity	NPC317383
0.8158	Intermediate Similarity	NPC472453
0.8156	Intermediate Similarity	NPC470990
0.8156	Intermediate Similarity	NPC72918
0.8154	Intermediate Similarity	NPC312800
0.8151	Intermediate Similarity	NPC53884
0.8151	Intermediate Similarity	NPC258671
0.8148	Intermediate Similarity	NPC288945
0.8148	Intermediate Similarity	NPC470163
0.8148	Intermediate Similarity	NPC470162
0.8146	Intermediate Similarity	NPC281477
0.8146	Intermediate Similarity	NPC281703
0.8146	Intermediate Similarity	NPC298802
0.8146	Intermediate Similarity	NPC125487
0.8138	Intermediate Similarity	NPC285550
0.8134	Intermediate Similarity	NPC297193
0.8134	Intermediate Similarity	NPC244351
0.8134	Intermediate Similarity	NPC46634
0.8133	Intermediate Similarity	NPC221249
0.8133	Intermediate Similarity	NPC227485
0.8133	Intermediate Similarity	NPC475076
0.8129	Intermediate Similarity	NPC470831
0.8129	Intermediate Similarity	NPC214702
0.8129	Intermediate Similarity	NPC318799
0.8117	Intermediate Similarity	NPC292415
0.8116	Intermediate Similarity	NPC94810
0.8112	Intermediate Similarity	NPC61590
0.8112	Intermediate Similarity	NPC191835
0.8112	Intermediate Similarity	NPC94248
0.8112	Intermediate Similarity	NPC33144
0.8112	Intermediate Similarity	NPC212693
0.8112	Intermediate Similarity	NPC478200
0.8108	Intermediate Similarity	NPC81835
0.8105	Intermediate Similarity	NPC77679
0.8105	Intermediate Similarity	NPC84935
0.8105	Intermediate Similarity	NPC129684
0.8105	Intermediate Similarity	NPC35598
0.8105	Intermediate Similarity	NPC190020
0.8105	Intermediate Similarity	NPC299520
0.8105	Intermediate Similarity	NPC222689
0.8102	Intermediate Similarity	NPC181715
0.8102	Intermediate Similarity	NPC214620
0.8099	Intermediate Similarity	NPC324929
0.8092	Intermediate Similarity	NPC286052
0.8092	Intermediate Similarity	NPC125252
0.8092	Intermediate Similarity	NPC269414
0.8092	Intermediate Similarity	NPC199926
0.8088	Intermediate Similarity	NPC280767
0.8082	Intermediate Similarity	NPC474692
0.8082	Intermediate Similarity	NPC21873
0.8082	Intermediate Similarity	NPC287722
0.8082	Intermediate Similarity	NPC476473
0.8082	Intermediate Similarity	NPC471417
0.8082	Intermediate Similarity	NPC304956
0.8079	Intermediate Similarity	NPC180388
0.8077	Intermediate Similarity	NPC474967
0.8074	Intermediate Similarity	NPC477152
0.8071	Intermediate Similarity	NPC111888
0.8071	Intermediate Similarity	NPC302844
0.8071	Intermediate Similarity	NPC50763
0.8069	Intermediate Similarity	NPC472904
0.8069	Intermediate Similarity	NPC478201
0.8069	Intermediate Similarity	NPC313123
0.8069	Intermediate Similarity	NPC478217
0.8069	Intermediate Similarity	NPC472035

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 NPC267539 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	831
0.2-0.3	1631
0.3-0.4	2564
0.4-0.5	2025
0.5-0.6	1195
0.6-0.7	516
0.7-0.8	122
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.854	High Similarity	NPD447	Suspended
0.8438	Intermediate Similarity	NPD9493	Approved
0.8406	Intermediate Similarity	NPD230	Phase 1
0.8298	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD9717	Approved
0.7943	Intermediate Similarity	NPD943	Approved
0.7914	Intermediate Similarity	NPD6832	Phase 2
0.7908	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1934	Approved
0.7826	Intermediate Similarity	NPD1203	Approved
0.7823	Intermediate Similarity	NPD8166	Discontinued
0.7812	Intermediate Similarity	NPD74	Approved
0.7812	Intermediate Similarity	NPD9266	Approved
0.7806	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3882	Suspended
0.7801	Intermediate Similarity	NPD411	Approved
0.7792	Intermediate Similarity	NPD2801	Approved
0.7762	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD9269	Phase 2
0.7734	Intermediate Similarity	NPD9263	Approved
0.7734	Intermediate Similarity	NPD9264	Approved
0.7734	Intermediate Similarity	NPD9267	Approved
0.7724	Intermediate Similarity	NPD2799	Discontinued
0.7724	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD9494	Approved
0.7703	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2313	Discontinued
0.7667	Intermediate Similarity	NPD1511	Approved
0.7643	Intermediate Similarity	NPD1019	Discontinued
0.764	Intermediate Similarity	NPD7473	Discontinued
0.7639	Intermediate Similarity	NPD1933	Approved
0.763	Intermediate Similarity	NPD9545	Approved
0.7628	Intermediate Similarity	NPD3817	Phase 2
0.7619	Intermediate Similarity	NPD2346	Discontinued
0.7616	Intermediate Similarity	NPD2534	Approved
0.7616	Intermediate Similarity	NPD2532	Approved
0.7616	Intermediate Similarity	NPD2533	Approved
0.7593	Intermediate Similarity	NPD3818	Discontinued
0.7566	Intermediate Similarity	NPD1512	Approved
0.7562	Intermediate Similarity	NPD6232	Discontinued
0.7551	Intermediate Similarity	NPD1551	Phase 2
0.7533	Intermediate Similarity	NPD6190	Approved
0.7532	Intermediate Similarity	NPD3455	Phase 2
0.7532	Intermediate Similarity	NPD7075	Discontinued
0.7518	Intermediate Similarity	NPD2798	Approved
0.7516	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7481	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6166	Phase 2
0.7469	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD9281	Approved
0.7452	Intermediate Similarity	NPD7819	Suspended
0.7452	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1164	Approved
0.7447	Intermediate Similarity	NPD2797	Approved
0.7445	Intermediate Similarity	NPD9268	Approved
0.7439	Intermediate Similarity	NPD7054	Approved
0.7434	Intermediate Similarity	NPD6799	Approved
0.7422	Intermediate Similarity	NPD9261	Approved
0.7396	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD7472	Approved
0.7383	Intermediate Similarity	NPD7266	Discontinued
0.7379	Intermediate Similarity	NPD520	Approved
0.7372	Intermediate Similarity	NPD4380	Phase 2
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7365	Intermediate Similarity	NPD4308	Phase 3
0.7365	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7768	Phase 2
0.7351	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3496	Discontinued
0.7329	Intermediate Similarity	NPD825	Approved
0.7329	Intermediate Similarity	NPD1240	Approved
0.7329	Intermediate Similarity	NPD826	Approved
0.7324	Intermediate Similarity	NPD1470	Approved
0.7315	Intermediate Similarity	NPD5404	Approved
0.7315	Intermediate Similarity	NPD5406	Approved
0.7315	Intermediate Similarity	NPD5405	Approved
0.7315	Intermediate Similarity	NPD5408	Approved
0.731	Intermediate Similarity	NPD3268	Approved
0.731	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD3226	Approved
0.7308	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7251	Discontinued
0.729	Intermediate Similarity	NPD5403	Approved
0.7279	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD2182	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6599	Discontinued
0.7246	Intermediate Similarity	NPD6797	Phase 2
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4628	Phase 3
0.7233	Intermediate Similarity	NPD1465	Phase 2
0.723	Intermediate Similarity	NPD1607	Approved
0.723	Intermediate Similarity	NPD6653	Approved
0.7222	Intermediate Similarity	NPD5494	Approved
0.7219	Intermediate Similarity	NPD8312	Approved
0.7219	Intermediate Similarity	NPD1549	Phase 2
0.7219	Intermediate Similarity	NPD8313	Approved
0.7215	Intermediate Similarity	NPD7411	Suspended
0.7205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6801	Discontinued
0.7164	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1201	Approved
0.7161	Intermediate Similarity	NPD5401	Approved
0.716	Intermediate Similarity	NPD6234	Discontinued
0.716	Intermediate Similarity	NPD7808	Phase 3
0.7153	Intermediate Similarity	NPD5647	Approved
0.7152	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5844	Phase 1
0.7124	Intermediate Similarity	NPD3750	Approved
0.7107	Intermediate Similarity	NPD2672	Discontinued
0.7101	Intermediate Similarity	NPD6559	Discontinued
0.7101	Intermediate Similarity	NPD7685	Pre-registration
0.7097	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4307	Phase 2
0.7095	Intermediate Similarity	NPD4060	Phase 1
0.709	Intermediate Similarity	NPD3021	Approved
0.709	Intermediate Similarity	NPD3022	Approved
0.7089	Intermediate Similarity	NPD7458	Discontinued
0.7086	Intermediate Similarity	NPD2796	Approved
0.7081	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6798	Discontinued
0.7075	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6844	Discontinued
0.7055	Intermediate Similarity	NPD919	Approved
0.7047	Intermediate Similarity	NPD555	Phase 2
0.7035	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD258	Approved
0.7034	Intermediate Similarity	NPD257	Approved
0.7032	Intermediate Similarity	NPD3300	Phase 2
0.7029	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4626	Approved
0.7021	Intermediate Similarity	NPD1778	Approved
0.702	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7003	Approved
0.7013	Intermediate Similarity	NPD4110	Phase 3
0.7007	Intermediate Similarity	NPD3027	Phase 3
0.7	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD6386	Approved
0.6993	Remote Similarity	NPD1608	Approved
0.6985	Remote Similarity	NPD228	Approved
0.6975	Remote Similarity	NPD5353	Approved
0.6974	Remote Similarity	NPD9570	Approved
0.697	Remote Similarity	NPD164	Approved
0.6968	Remote Similarity	NPD2309	Approved
0.6966	Remote Similarity	NPD3266	Approved
0.6966	Remote Similarity	NPD3267	Approved
0.6964	Remote Similarity	NPD7228	Approved
0.6962	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD920	Approved
0.6957	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2629	Approved
0.6957	Remote Similarity	NPD37	Approved
0.695	Remote Similarity	NPD5691	Approved
0.6946	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.694	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4967	Phase 2
0.6933	Remote Similarity	NPD4966	Approved
0.6933	Remote Similarity	NPD4965	Approved
0.6928	Remote Similarity	NPD6005	Phase 3
0.6928	Remote Similarity	NPD6002	Phase 3
0.6928	Remote Similarity	NPD5711	Approved
0.6928	Remote Similarity	NPD6004	Phase 3
0.6928	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5710	Approved
0.6923	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7286	Phase 2
0.6918	Remote Similarity	NPD1653	Approved
0.6913	Remote Similarity	NPD259	Phase 1
0.6913	Remote Similarity	NPD6663	Approved
0.6913	Remote Similarity	NPD6233	Phase 2
0.6908	Remote Similarity	NPD7033	Discontinued
0.6906	Remote Similarity	NPD6671	Approved
0.6899	Remote Similarity	NPD6273	Approved
0.6897	Remote Similarity	NPD1283	Approved
0.6892	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3749	Approved
0.6889	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6651	Approved
0.6871	Remote Similarity	NPD5736	Approved
0.6867	Remote Similarity	NPD8127	Discontinued
0.6867	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2979	Phase 3
0.6867	Remote Similarity	NPD1613	Approved
0.6867	Remote Similarity	NPD1247	Approved
0.6866	Remote Similarity	NPD3134	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