NPASS Compound

Structure

CID131329 OpenBabel06191715492D 29 30 0 0 1 0 0 0 0 0999 V2000 -1.7424 -5.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 -2.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -4.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 -3.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5176 -3.9319 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -1.4836 -3.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 24 1 6 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 26 2 0 0 0 0 17 29 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 1 0 0 0 21 29 1 1 0 0 0 23 27 1 0 0 0 0 24 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.27
Volume:	439.952
LogP:	3.965
LogD:	3.029
LogS:	-4.393
# Rotatable Bonds:	8
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.51
Synthetic Accessibility Score:	4.795
Fsp3:	0.75
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:	-4.692
MDCK Permeability:	1.952372258529067e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.639
Plasma Protein Binding (PPB):	85.20824432373047%
Volume Distribution (VD):	1.879
Pgp-substrate:	14.159104347229004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.208
CYP2C19-substrate:	0.746
CYP2C9-inhibitor:	0.289
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.3
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.475

ADMET: Excretion

Clearance (CL):	2.236
Half-life (T1/2):	0.091

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.394
Drug-inuced Liver Injury (DILI):	0.824
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.084
Carcinogencity:	0.452
Eye Corrosion:	0.162
Eye Irritation:	0.134
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC131329

Natural Product ID:	NPC131329
*Common Name:**	Vitetrifolin D
IUPAC Name:	[(1S,2R,3S,4R)-1-acetyloxy-4-(3-hydroxy-3-methylpent-4-enyl)-3,4,8,8-tetramethyl-1,2,3,5,6,7-hexahydronaphthalen-2-yl] acetate
Synonyms:
Standard InCHIKey:	JSGVRMXIAILPPO-FWPWNEHFSA-N
Standard InCHI:	InChI=1S/C24H38O5/c1-9-23(7,27)13-14-24(8)15(2)20(28-16(3)25)21(29-17(4)26)19-18(24)11-10-12-22(19,5)6/h9,15,20-21,27H,1,10-14H2,2-8H3/t15-,20-,21+,23?,24-/m1/s1
SMILES:	C=CC(CC[C@]1(C)[C@H](C)[C@@H](OC(=O)C)[C@H](C2=C1CCCC2(C)C)OC(=O)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436600
PubChem CID:	11015016
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids and derivatives

*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
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15577254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15621610]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23327905]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28453270]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21373	Vitex trifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

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	Activity	>	90.0	%	PMID[543619]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	24500.0	nM	PMID[543619]

☑ 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 NPC131329 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	183
0.1-0.2	1227
0.2-0.3	4563
0.3-0.4	13272
0.4-0.5	11696
0.5-0.6	7292
0.6-0.7	4014
0.7-0.8	428
0.8-0.85	17
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC20946
0.9518	High Similarity	NPC245004
0.9048	High Similarity	NPC35933
0.8916	High Similarity	NPC471408
0.8851	High Similarity	NPC246028
0.881	High Similarity	NPC49208
0.8795	High Similarity	NPC25554
0.8652	High Similarity	NPC477574
0.8588	High Similarity	NPC23748
0.8478	Intermediate Similarity	NPC57664
0.8471	Intermediate Similarity	NPC256112
0.8462	Intermediate Similarity	NPC472416
0.8462	Intermediate Similarity	NPC472360
0.8452	Intermediate Similarity	NPC233332
0.8444	Intermediate Similarity	NPC177641
0.8427	Intermediate Similarity	NPC82876
0.8409	Intermediate Similarity	NPC166857
0.8387	Intermediate Similarity	NPC473244
0.8372	Intermediate Similarity	NPC476927
0.8352	Intermediate Similarity	NPC53555
0.8333	Intermediate Similarity	NPC78973
0.8333	Intermediate Similarity	NPC242767
0.828	Intermediate Similarity	NPC284194
0.828	Intermediate Similarity	NPC221801
0.828	Intermediate Similarity	NPC471765
0.828	Intermediate Similarity	NPC211810
0.8229	Intermediate Similarity	NPC11956
0.8222	Intermediate Similarity	NPC16265
0.8211	Intermediate Similarity	NPC473510
0.8211	Intermediate Similarity	NPC38855
0.8191	Intermediate Similarity	NPC210337
0.8152	Intermediate Similarity	NPC27918
0.8144	Intermediate Similarity	NPC23584
0.814	Intermediate Similarity	NPC142163
0.814	Intermediate Similarity	NPC170303
0.8132	Intermediate Similarity	NPC220216
0.8125	Intermediate Similarity	NPC472554
0.8118	Intermediate Similarity	NPC233295
0.8105	Intermediate Similarity	NPC247233
0.8095	Intermediate Similarity	NPC283619
0.8095	Intermediate Similarity	NPC40049
0.809	Intermediate Similarity	NPC475069
0.809	Intermediate Similarity	NPC175145
0.8085	Intermediate Similarity	NPC88009
0.8085	Intermediate Similarity	NPC129569
0.8068	Intermediate Similarity	NPC306951
0.8065	Intermediate Similarity	NPC474922
0.8065	Intermediate Similarity	NPC182826
0.8065	Intermediate Similarity	NPC105375
0.8061	Intermediate Similarity	NPC473543
0.8046	Intermediate Similarity	NPC2524
0.8046	Intermediate Similarity	NPC471218
0.8043	Intermediate Similarity	NPC124374
0.8043	Intermediate Similarity	NPC41239
0.8043	Intermediate Similarity	NPC329842
0.8041	Intermediate Similarity	NPC472552
0.8022	Intermediate Similarity	NPC261320
0.8021	Intermediate Similarity	NPC230546
0.8	Intermediate Similarity	NPC471779
0.8	Intermediate Similarity	NPC254496
0.7979	Intermediate Similarity	NPC276110
0.7978	Intermediate Similarity	NPC109528
0.7976	Intermediate Similarity	NPC265588
0.7959	Intermediate Similarity	NPC473523
0.7957	Intermediate Similarity	NPC99653
0.7957	Intermediate Similarity	NPC7349
0.7955	Intermediate Similarity	NPC474789
0.7955	Intermediate Similarity	NPC52108
0.7955	Intermediate Similarity	NPC474809
0.7938	Intermediate Similarity	NPC475617
0.7931	Intermediate Similarity	NPC159148
0.7912	Intermediate Similarity	NPC473879
0.7912	Intermediate Similarity	NPC24816
0.7907	Intermediate Similarity	NPC100906
0.79	Intermediate Similarity	NPC301666
0.7895	Intermediate Similarity	NPC190713
0.7895	Intermediate Similarity	NPC473153
0.7889	Intermediate Similarity	NPC329692
0.7889	Intermediate Similarity	NPC473226
0.7889	Intermediate Similarity	NPC131813
0.7889	Intermediate Similarity	NPC474970
0.7889	Intermediate Similarity	NPC471219
0.7889	Intermediate Similarity	NPC281316
0.7872	Intermediate Similarity	NPC469491
0.7872	Intermediate Similarity	NPC105490
0.7865	Intermediate Similarity	NPC102048
0.7865	Intermediate Similarity	NPC302360
0.7857	Intermediate Similarity	NPC476471
0.7857	Intermediate Similarity	NPC475344
0.7849	Intermediate Similarity	NPC303697
0.7849	Intermediate Similarity	NPC234335
0.7849	Intermediate Similarity	NPC472811
0.7841	Intermediate Similarity	NPC155521
0.7841	Intermediate Similarity	NPC474979
0.7835	Intermediate Similarity	NPC188968
0.7835	Intermediate Similarity	NPC79303
0.7835	Intermediate Similarity	NPC474190
0.7835	Intermediate Similarity	NPC271295
0.7826	Intermediate Similarity	NPC49783
0.7826	Intermediate Similarity	NPC473647
0.7826	Intermediate Similarity	NPC314727
0.7826	Intermediate Similarity	NPC115607
0.7822	Intermediate Similarity	NPC50124
0.7816	Intermediate Similarity	NPC281880
0.7816	Intermediate Similarity	NPC474592
0.7816	Intermediate Similarity	NPC469802
0.7816	Intermediate Similarity	NPC269791
0.7812	Intermediate Similarity	NPC73911
0.7812	Intermediate Similarity	NPC141401
0.7812	Intermediate Similarity	NPC205143
0.7812	Intermediate Similarity	NPC285513
0.7802	Intermediate Similarity	NPC149224
0.7802	Intermediate Similarity	NPC476948
0.7789	Intermediate Similarity	NPC134067
0.7789	Intermediate Similarity	NPC476720
0.7789	Intermediate Similarity	NPC472441
0.7789	Intermediate Similarity	NPC53565
0.7778	Intermediate Similarity	NPC474124
0.7778	Intermediate Similarity	NPC274448
0.7778	Intermediate Similarity	NPC474013
0.7778	Intermediate Similarity	NPC164424
0.7778	Intermediate Similarity	NPC477578
0.7766	Intermediate Similarity	NPC205034
0.7766	Intermediate Similarity	NPC162615
0.7766	Intermediate Similarity	NPC472812
0.7766	Intermediate Similarity	NPC152778
0.7766	Intermediate Similarity	NPC38232
0.7755	Intermediate Similarity	NPC280991
0.7755	Intermediate Similarity	NPC473160
0.7755	Intermediate Similarity	NPC303559
0.7753	Intermediate Similarity	NPC57370
0.7753	Intermediate Similarity	NPC79945
0.7745	Intermediate Similarity	NPC5475
0.7745	Intermediate Similarity	NPC472216
0.7745	Intermediate Similarity	NPC475586
0.7745	Intermediate Similarity	NPC284828
0.7745	Intermediate Similarity	NPC173905
0.7742	Intermediate Similarity	NPC473269
0.7742	Intermediate Similarity	NPC48732
0.7742	Intermediate Similarity	NPC182136
0.7742	Intermediate Similarity	NPC310479
0.7742	Intermediate Similarity	NPC221111
0.7742	Intermediate Similarity	NPC295668
0.7742	Intermediate Similarity	NPC472307
0.7742	Intermediate Similarity	NPC280149
0.7738	Intermediate Similarity	NPC71152
0.7738	Intermediate Similarity	NPC104644
0.7732	Intermediate Similarity	NPC218107
0.7732	Intermediate Similarity	NPC478056
0.7732	Intermediate Similarity	NPC278386
0.7732	Intermediate Similarity	NPC92275
0.7732	Intermediate Similarity	NPC124512
0.7732	Intermediate Similarity	NPC316598
0.7732	Intermediate Similarity	NPC159763
0.7727	Intermediate Similarity	NPC475944
0.7723	Intermediate Similarity	NPC475176
0.7723	Intermediate Similarity	NPC67321
0.7723	Intermediate Similarity	NPC187435
0.7717	Intermediate Similarity	NPC93411
0.7717	Intermediate Similarity	NPC7280
0.7717	Intermediate Similarity	NPC477128
0.7717	Intermediate Similarity	NPC229612
0.7708	Intermediate Similarity	NPC276103
0.7708	Intermediate Similarity	NPC288970
0.7708	Intermediate Similarity	NPC54248
0.7708	Intermediate Similarity	NPC16967
0.7701	Intermediate Similarity	NPC471537
0.77	Intermediate Similarity	NPC118911
0.7692	Intermediate Similarity	NPC73038
0.7692	Intermediate Similarity	NPC82979
0.7692	Intermediate Similarity	NPC255143
0.7692	Intermediate Similarity	NPC286153
0.7692	Intermediate Similarity	NPC102996
0.7684	Intermediate Similarity	NPC57117
0.7684	Intermediate Similarity	NPC215700
0.7684	Intermediate Similarity	NPC470255
0.7684	Intermediate Similarity	NPC298973
0.7684	Intermediate Similarity	NPC38830
0.7684	Intermediate Similarity	NPC279410
0.7684	Intermediate Similarity	NPC119562
0.7684	Intermediate Similarity	NPC91010
0.7684	Intermediate Similarity	NPC201725
0.7684	Intermediate Similarity	NPC104925
0.7677	Intermediate Similarity	NPC137430
0.7677	Intermediate Similarity	NPC472815
0.7677	Intermediate Similarity	NPC273668
0.7677	Intermediate Similarity	NPC471363
0.7677	Intermediate Similarity	NPC258547
0.7677	Intermediate Similarity	NPC80781
0.7677	Intermediate Similarity	NPC283343
0.7677	Intermediate Similarity	NPC238397
0.7677	Intermediate Similarity	NPC470571
0.7674	Intermediate Similarity	NPC132542
0.7674	Intermediate Similarity	NPC91594
0.7667	Intermediate Similarity	NPC83702
0.7667	Intermediate Similarity	NPC96055
0.7667	Intermediate Similarity	NPC46320
0.7667	Intermediate Similarity	NPC470077
0.766	Intermediate Similarity	NPC72845
0.766	Intermediate Similarity	NPC26888

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 NPC131329 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1678
0.2-0.3	3721
0.3-0.4	2406
0.4-0.5	812
0.5-0.6	310
0.6-0.7	64
0.7-0.8	5
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
0.7732	Intermediate Similarity	NPD4225	Approved
0.7475	Intermediate Similarity	NPD7640	Approved
0.7475	Intermediate Similarity	NPD7639	Approved
0.7442	Intermediate Similarity	NPD8264	Approved
0.7407	Intermediate Similarity	NPD7115	Discovery
0.74	Intermediate Similarity	NPD5344	Discontinued
0.7374	Intermediate Similarity	NPD7638	Approved
0.73	Intermediate Similarity	NPD6648	Approved
0.7263	Intermediate Similarity	NPD6051	Approved
0.7216	Intermediate Similarity	NPD5779	Approved
0.7216	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7113	Intermediate Similarity	NPD6411	Approved
0.7097	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6399	Phase 3
0.7021	Intermediate Similarity	NPD1694	Approved
0.699	Remote Similarity	NPD7632	Discontinued
0.6939	Remote Similarity	NPD7515	Phase 2
0.6931	Remote Similarity	NPD7902	Approved
0.6923	Remote Similarity	NPD7645	Phase 2
0.6916	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6101	Approved
0.6852	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7525	Registered
0.6768	Remote Similarity	NPD7637	Suspended
0.6727	Remote Similarity	NPD8297	Approved
0.6726	Remote Similarity	NPD7328	Approved
0.6726	Remote Similarity	NPD7327	Approved
0.6702	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7524	Approved
0.6699	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7503	Approved
0.6696	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.6636	Remote Similarity	NPD6675	Approved
0.6636	Remote Similarity	NPD6402	Approved
0.6636	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD5739	Approved
0.6634	Remote Similarity	NPD7900	Approved
0.6634	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6695	Phase 3
0.6609	Remote Similarity	NPD8377	Approved
0.6609	Remote Similarity	NPD8294	Approved
0.6593	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5697	Approved
0.6571	Remote Similarity	NPD4159	Approved
0.6569	Remote Similarity	NPD5695	Phase 3
0.6562	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4786	Approved
0.6552	Remote Similarity	NPD8335	Approved
0.6552	Remote Similarity	NPD8380	Approved
0.6552	Remote Similarity	NPD8379	Approved
0.6552	Remote Similarity	NPD8378	Approved
0.6552	Remote Similarity	NPD8296	Approved
0.6545	Remote Similarity	NPD7102	Approved
0.6545	Remote Similarity	NPD6883	Approved
0.6545	Remote Similarity	NPD7290	Approved
0.6531	Remote Similarity	NPD3573	Approved
0.6531	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3667	Approved
0.6514	Remote Similarity	NPD7320	Approved
0.6514	Remote Similarity	NPD6686	Approved
0.6514	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6698	Approved
0.65	Remote Similarity	NPD46	Approved
0.65	Remote Similarity	NPD5785	Approved
0.6489	Remote Similarity	NPD4821	Approved
0.6489	Remote Similarity	NPD4822	Approved
0.6489	Remote Similarity	NPD4820	Approved
0.6489	Remote Similarity	NPD4748	Discontinued
0.6489	Remote Similarity	NPD4819	Approved
0.6489	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6869	Approved
0.6486	Remote Similarity	NPD6649	Approved
0.6486	Remote Similarity	NPD6617	Approved
0.6486	Remote Similarity	NPD8130	Phase 1
0.6486	Remote Similarity	NPD6847	Approved
0.6486	Remote Similarity	NPD6650	Approved
0.6458	Remote Similarity	NPD5362	Discontinued
0.6458	Remote Similarity	NPD7154	Phase 3
0.6455	Remote Similarity	NPD6372	Approved
0.6455	Remote Similarity	NPD6012	Approved
0.6455	Remote Similarity	NPD6013	Approved
0.6455	Remote Similarity	NPD6373	Approved
0.6455	Remote Similarity	NPD6014	Approved
0.6455	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6084	Phase 2
0.6442	Remote Similarity	NPD6083	Phase 2
0.6436	Remote Similarity	NPD8034	Phase 2
0.6436	Remote Similarity	NPD6079	Approved
0.6436	Remote Similarity	NPD8035	Phase 2
0.6429	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6409	Approved
0.6429	Remote Similarity	NPD368	Approved
0.6429	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD7521	Approved
0.6429	Remote Similarity	NPD5330	Approved
0.6429	Remote Similarity	NPD6882	Approved
0.6429	Remote Similarity	NPD7334	Approved
0.6429	Remote Similarity	NPD7146	Approved
0.6422	Remote Similarity	NPD5701	Approved
0.6413	Remote Similarity	NPD6933	Approved
0.641	Remote Similarity	NPD8513	Phase 3
0.641	Remote Similarity	NPD8516	Approved
0.641	Remote Similarity	NPD8515	Approved
0.641	Remote Similarity	NPD8517	Approved
0.64	Remote Similarity	NPD5328	Approved
0.64	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4784	Approved
0.6374	Remote Similarity	NPD6926	Approved
0.6374	Remote Similarity	NPD4785	Approved
0.6374	Remote Similarity	NPD6924	Approved
0.6372	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD7750	Discontinued
0.6355	Remote Similarity	NPD5211	Phase 2
0.6339	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7507	Approved
0.6327	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1696	Phase 3
0.6327	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6931	Approved
0.6316	Remote Similarity	NPD6930	Phase 2
0.6316	Remote Similarity	NPD7332	Phase 2
0.6316	Remote Similarity	NPD7514	Phase 3
0.6316	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6903	Approved
0.63	Remote Similarity	NPD5737	Approved
0.63	Remote Similarity	NPD6672	Approved
0.6289	Remote Similarity	NPD5331	Approved
0.6289	Remote Similarity	NPD5332	Approved
0.6283	Remote Similarity	NPD6053	Discontinued
0.6277	Remote Similarity	NPD4268	Approved
0.6277	Remote Similarity	NPD4271	Approved
0.6275	Remote Similarity	NPD5281	Approved
0.6275	Remote Similarity	NPD5693	Phase 1
0.6275	Remote Similarity	NPD7983	Approved
0.6275	Remote Similarity	NPD5284	Approved
0.6263	Remote Similarity	NPD4623	Approved
0.6263	Remote Similarity	NPD4519	Discontinued
0.625	Remote Similarity	NPD4790	Discontinued
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6371	Approved
0.6239	Remote Similarity	NPD5141	Approved
0.6226	Remote Similarity	NPD5696	Approved
0.6224	Remote Similarity	NPD3668	Phase 3
0.6214	Remote Similarity	NPD4202	Approved
0.6211	Remote Similarity	NPD4195	Approved
0.6211	Remote Similarity	NPD6929	Approved
0.621	Remote Similarity	NPD7260	Phase 2
0.6207	Remote Similarity	NPD6009	Approved
0.6195	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5222	Approved
0.619	Remote Similarity	NPD5221	Approved
0.6186	Remote Similarity	NPD4270	Approved
0.6186	Remote Similarity	NPD6319	Approved
0.6186	Remote Similarity	NPD4269	Approved
0.6182	Remote Similarity	NPD6008	Approved
0.6179	Remote Similarity	NPD7319	Approved
0.6168	Remote Similarity	NPD5286	Approved
0.6168	Remote Similarity	NPD4696	Approved
0.6168	Remote Similarity	NPD5285	Approved
0.6167	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD7152	Approved
0.6154	Remote Similarity	NPD4243	Approved
0.6154	Remote Similarity	NPD7150	Approved
0.6154	Remote Similarity	NPD7151	Approved
0.6154	Remote Similarity	NPD6335	Approved
0.6148	Remote Similarity	NPD8074	Phase 3
0.6146	Remote Similarity	NPD7509	Discontinued
0.6134	Remote Similarity	NPD5983	Phase 2
0.6132	Remote Similarity	NPD4755	Approved
0.6132	Remote Similarity	NPD5173	Approved
0.6121	Remote Similarity	NPD6868	Approved
0.6117	Remote Similarity	NPD6050	Approved
0.6117	Remote Similarity	NPD5694	Approved
0.6117	Remote Similarity	NPD7087	Discontinued
0.6116	Remote Similarity	NPD7492	Approved
0.6111	Remote Similarity	NPD5223	Approved
0.6105	Remote Similarity	NPD7145	Approved
0.6102	Remote Similarity	NPD7101	Approved
0.6102	Remote Similarity	NPD7100	Approved
0.61	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6098	Approved
0.61	Remote Similarity	NPD5786	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