NPASS Compound

Structure

CID192 OpenBabel06191715322D 22 22 0 0 0 0 0 0 0 0999 V2000 0.8660 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 0.8660 -2.5000 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 0.8660 0.5000 0.0000 C 0 0 0 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 -1.5000 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 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 16 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 20 1 0 0 0 0 18 21 2 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.23
Volume:	356.187
LogP:	5.112
LogD:	4.395
LogS:	-3.218
# Rotatable Bonds:	12
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	2.527
Fsp3:	0.429
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:	-4.923
MDCK Permeability:	3.6622892366722226e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.412
Plasma Protein Binding (PPB):	100.15998077392578%
Volume Distribution (VD):	1.934
Pgp-substrate:	0.3888793885707855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.829
CYP1A2-substrate:	0.468
CYP2C19-inhibitor:	0.868
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.958
CYP2D6-substrate:	0.935
CYP3A4-inhibitor:	0.858
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	5.662
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.16
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.97
Carcinogencity:	0.302
Eye Corrosion:	0.636
Eye Irritation:	0.973
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC192

Natural Product ID:	NPC192
*Common Name:**	Cardanol
IUPAC Name:	3-[(8Z,11Z)-pentadeca-8,11,14-trienyl]phenol
Synonyms:	5-{8(Z),11(Z),14-Pentadecatrienyl}Phenol; Cardanol
Standard InCHIKey:	JOLVYUIAMRUBRK-UTOQUPLUSA-N
Standard InCHI:	InChI=1S/C21H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-20-17-15-18-21(22)19-20/h2,4-5,7-8,15,17-19,22H,1,3,6,9-14,16H2/b5-4-,8-7-
SMILES:	C=CC/C=CC/C=CCCCCCCCc1cccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470680
PubChem CID:	11266523
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654416]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[14577694]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20014777]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	seeds	n.a.	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	seed	n.a.	PMID[21942765]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22459211]
NPO29940	Schinus terebinthifolius	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2723668]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29940	Schinus terebinthifolius	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22456	Schinus terebinthifolia	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29940	Schinus terebinthifolius	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1744	Discaria serratifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10494	Alpinia katsumadai	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9180	Pyrostegia venusta	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12510	Aronia arbutifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO998	Justicia hayatai	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13070	Clibadium mexiae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13016	Viscaria viscosa	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11636	Ideopsis similis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22456	Schinus terebinthifolia	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3469	Pteris dactylina	Species	Pteridaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT89	Individual Protein	Seed lipoxygenase-1	Glycine max	IC50	=	100000.0	nM	PMID[489862]

☑ 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 NPC192 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	289
0.1-0.2	2047
0.2-0.3	6352
0.3-0.4	12654
0.4-0.5	6862
0.5-0.6	9445
0.6-0.7	3741
0.7-0.8	957
0.8-0.85	174
0.85-0.9	124
0.9-0.95	38
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC3358
0.977	High Similarity	NPC162314
0.977	High Similarity	NPC147284
0.977	High Similarity	NPC306884
0.977	High Similarity	NPC94139
0.977	High Similarity	NPC210497
0.9659	High Similarity	NPC76938
0.9551	High Similarity	NPC32714
0.9535	High Similarity	NPC27974
0.9326	High Similarity	NPC55903
0.9205	High Similarity	NPC280347
0.9205	High Similarity	NPC177420
0.9205	High Similarity	NPC242240
0.9205	High Similarity	NPC318325
0.9205	High Similarity	NPC123273
0.9186	High Similarity	NPC150837
0.914	High Similarity	NPC129373
0.914	High Similarity	NPC248396
0.914	High Similarity	NPC48730
0.914	High Similarity	NPC10588
0.914	High Similarity	NPC294741
0.913	High Similarity	NPC6597
0.913	High Similarity	NPC79241
0.913	High Similarity	NPC152097
0.913	High Similarity	NPC474073
0.9121	High Similarity	NPC274678
0.9121	High Similarity	NPC222146
0.9101	High Similarity	NPC55561
0.9091	High Similarity	NPC25493
0.9091	High Similarity	NPC19680
0.9091	High Similarity	NPC113460
0.908	High Similarity	NPC155393
0.9043	High Similarity	NPC252105
0.9043	High Similarity	NPC72947
0.9043	High Similarity	NPC284011
0.9032	High Similarity	NPC299762
0.9032	High Similarity	NPC260775
0.9032	High Similarity	NPC33675
0.9022	High Similarity	NPC312132
0.9022	High Similarity	NPC259512
0.9011	High Similarity	NPC245187
0.9011	High Similarity	NPC27323
0.9011	High Similarity	NPC316301
0.9011	High Similarity	NPC152415
0.9011	High Similarity	NPC151715
0.9	High Similarity	NPC304541
0.9	High Similarity	NPC231150
0.8989	High Similarity	NPC258219
0.8977	High Similarity	NPC407
0.8977	High Similarity	NPC307235
0.8977	High Similarity	NPC23167
0.8966	High Similarity	NPC175313
0.8947	High Similarity	NPC71002
0.8947	High Similarity	NPC94351
0.8947	High Similarity	NPC249828
0.8947	High Similarity	NPC168303
0.8947	High Similarity	NPC146798
0.8947	High Similarity	NPC24404
0.8947	High Similarity	NPC313030
0.8947	High Similarity	NPC106396
0.8947	High Similarity	NPC302219
0.8947	High Similarity	NPC242342
0.8947	High Similarity	NPC222522
0.8947	High Similarity	NPC85479
0.8947	High Similarity	NPC108497
0.8947	High Similarity	NPC53051
0.8936	High Similarity	NPC12931
0.8936	High Similarity	NPC130756
0.8936	High Similarity	NPC70677
0.8936	High Similarity	NPC166761
0.8936	High Similarity	NPC72729
0.8925	High Similarity	NPC475078
0.8913	High Similarity	NPC26244
0.8889	High Similarity	NPC312304
0.8864	High Similarity	NPC197783
0.8854	High Similarity	NPC323810
0.8854	High Similarity	NPC241891
0.8851	High Similarity	NPC265146
0.8842	High Similarity	NPC166313
0.8842	High Similarity	NPC24407
0.8842	High Similarity	NPC137415
0.8842	High Similarity	NPC147310
0.8842	High Similarity	NPC192032
0.8842	High Similarity	NPC11280
0.8842	High Similarity	NPC477685
0.8842	High Similarity	NPC294186
0.8817	High Similarity	NPC292730
0.8817	High Similarity	NPC82664
0.8817	High Similarity	NPC473388
0.8817	High Similarity	NPC132271
0.8817	High Similarity	NPC202986
0.8817	High Similarity	NPC216520
0.8791	High Similarity	NPC155908
0.8791	High Similarity	NPC45040
0.8791	High Similarity	NPC306074
0.8778	High Similarity	NPC98772
0.8764	High Similarity	NPC184169
0.8763	High Similarity	NPC47284
0.8763	High Similarity	NPC134829
0.875	High Similarity	NPC286904
0.875	High Similarity	NPC196479
0.875	High Similarity	NPC248817
0.875	High Similarity	NPC235762
0.875	High Similarity	NPC471228
0.8737	High Similarity	NPC174911
0.8737	High Similarity	NPC211885
0.8737	High Similarity	NPC225506
0.8723	High Similarity	NPC156313
0.8723	High Similarity	NPC77492
0.8723	High Similarity	NPC32674
0.8723	High Similarity	NPC225464
0.8723	High Similarity	NPC109955
0.8696	High Similarity	NPC29373
0.8696	High Similarity	NPC271440
0.8681	High Similarity	NPC300017
0.8673	High Similarity	NPC155072
0.8673	High Similarity	NPC118286
0.8673	High Similarity	NPC477814
0.8673	High Similarity	NPC109691
0.8673	High Similarity	NPC302681
0.8673	High Similarity	NPC470700
0.8673	High Similarity	NPC39664
0.8673	High Similarity	NPC39097
0.8673	High Similarity	NPC53740
0.866	High Similarity	NPC475225
0.8646	High Similarity	NPC12221
0.8646	High Similarity	NPC143659
0.8646	High Similarity	NPC80800
0.8646	High Similarity	NPC100340
0.8636	High Similarity	NPC124436
0.8632	High Similarity	NPC122005
0.8632	High Similarity	NPC78119
0.8632	High Similarity	NPC252821
0.8632	High Similarity	NPC132078
0.8632	High Similarity	NPC51333
0.8632	High Similarity	NPC92730
0.8632	High Similarity	NPC216468
0.8602	High Similarity	NPC289769
0.8602	High Similarity	NPC128062
0.8587	High Similarity	NPC270547
0.8587	High Similarity	NPC204210
0.8586	High Similarity	NPC232523
0.8586	High Similarity	NPC54844
0.8586	High Similarity	NPC158253
0.8586	High Similarity	NPC305603
0.8586	High Similarity	NPC61033
0.8586	High Similarity	NPC320439
0.8586	High Similarity	NPC204901
0.8571	High Similarity	NPC37802
0.8571	High Similarity	NPC246056
0.8571	High Similarity	NPC117115
0.8557	High Similarity	NPC269212
0.8557	High Similarity	NPC168829
0.8542	High Similarity	NPC213730
0.8542	High Similarity	NPC130103
0.8511	High Similarity	NPC257182
0.8511	High Similarity	NPC8392
0.85	High Similarity	NPC11554
0.8495	Intermediate Similarity	NPC325292
0.8495	Intermediate Similarity	NPC138117
0.8485	Intermediate Similarity	NPC310456
0.8485	Intermediate Similarity	NPC469913
0.8485	Intermediate Similarity	NPC99836
0.8485	Intermediate Similarity	NPC12640
0.8485	Intermediate Similarity	NPC201662
0.8469	Intermediate Similarity	NPC218879
0.8469	Intermediate Similarity	NPC120719
0.8469	Intermediate Similarity	NPC244513
0.8469	Intermediate Similarity	NPC102216
0.8469	Intermediate Similarity	NPC288411
0.8469	Intermediate Similarity	NPC327811
0.8469	Intermediate Similarity	NPC227458
0.8469	Intermediate Similarity	NPC471511
0.8469	Intermediate Similarity	NPC475580
0.8469	Intermediate Similarity	NPC254965
0.8469	Intermediate Similarity	NPC30506
0.8462	Intermediate Similarity	NPC104216
0.8454	Intermediate Similarity	NPC40258
0.8454	Intermediate Similarity	NPC110764
0.8454	Intermediate Similarity	NPC91461
0.8454	Intermediate Similarity	NPC7686
0.8438	Intermediate Similarity	NPC128723
0.8416	Intermediate Similarity	NPC62258
0.8416	Intermediate Similarity	NPC254833
0.8416	Intermediate Similarity	NPC228343
0.8416	Intermediate Similarity	NPC55617
0.8416	Intermediate Similarity	NPC19808
0.8416	Intermediate Similarity	NPC33728
0.84	Intermediate Similarity	NPC66834
0.84	Intermediate Similarity	NPC151477
0.8384	Intermediate Similarity	NPC138942
0.8384	Intermediate Similarity	NPC239291
0.837	Intermediate Similarity	NPC70436
0.8367	Intermediate Similarity	NPC233827
0.8367	Intermediate Similarity	NPC68055
0.8367	Intermediate Similarity	NPC168393
0.8333	Intermediate Similarity	NPC147634
0.8333	Intermediate Similarity	NPC13482
0.8333	Intermediate Similarity	NPC79793
0.8333	Intermediate Similarity	NPC470161

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 NPC192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	1068
0.2-0.3	1337
0.3-0.4	2895
0.4-0.5	1929
0.5-0.6	1105
0.6-0.7	427
0.7-0.8	66
0.8-0.85	10
0.85-0.9	8
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD844	Approved
0.9022	High Similarity	NPD288	Approved
0.9011	High Similarity	NPD1432	Clinical (unspecified phase)
0.8913	High Similarity	NPD2859	Approved
0.8913	High Similarity	NPD2860	Approved
0.883	High Similarity	NPD3020	Approved
0.8804	High Similarity	NPD2934	Approved
0.8804	High Similarity	NPD2933	Approved
0.8737	High Similarity	NPD289	Clinical (unspecified phase)
0.8696	High Similarity	NPD845	Approved
0.8636	High Similarity	NPD111	Approved
0.8485	Intermediate Similarity	NPD1445	Approved
0.8485	Intermediate Similarity	NPD1444	Approved
0.8416	Intermediate Similarity	NPD3022	Approved
0.8416	Intermediate Similarity	NPD3021	Approved
0.8316	Intermediate Similarity	NPD1809	Phase 2
0.8265	Intermediate Similarity	NPD846	Approved
0.8265	Intermediate Similarity	NPD940	Approved
0.8235	Intermediate Similarity	NPD1792	Phase 2
0.8235	Intermediate Similarity	NPD4750	Phase 3
0.8218	Intermediate Similarity	NPD2342	Discontinued
0.8163	Intermediate Similarity	NPD1242	Phase 1
0.8	Intermediate Similarity	NPD9087	Approved
0.8	Intermediate Similarity	NPD9500	Approved
0.8	Intermediate Similarity	NPD7635	Approved
0.7944	Intermediate Similarity	NPD6671	Approved
0.785	Intermediate Similarity	NPD1793	Approved
0.785	Intermediate Similarity	NPD1791	Approved
0.7757	Intermediate Similarity	NPD2229	Approved
0.7757	Intermediate Similarity	NPD2228	Approved
0.7757	Intermediate Similarity	NPD2234	Approved
0.7745	Intermediate Similarity	NPD9610	Approved
0.7745	Intermediate Similarity	NPD9608	Approved
0.7736	Intermediate Similarity	NPD228	Approved
0.7727	Intermediate Similarity	NPD9294	Approved
0.7727	Intermediate Similarity	NPD3091	Approved
0.7664	Intermediate Similarity	NPD9379	Approved
0.7664	Intermediate Similarity	NPD9377	Approved
0.7658	Intermediate Similarity	NPD4093	Discontinued
0.764	Intermediate Similarity	NPD9088	Approved
0.7624	Intermediate Similarity	NPD3028	Approved
0.76	Intermediate Similarity	NPD9273	Approved
0.7589	Intermediate Similarity	NPD2932	Approved
0.7589	Intermediate Similarity	NPD4059	Approved
0.7589	Intermediate Similarity	NPD3019	Approved
0.7568	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD9614	Approved
0.7523	Intermediate Similarity	NPD9618	Approved
0.7456	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3092	Approved
0.7456	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2684	Approved
0.7434	Intermediate Similarity	NPD2286	Discontinued
0.7434	Intermediate Similarity	NPD1751	Approved
0.7429	Intermediate Similarity	NPD968	Approved
0.7407	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD9616	Approved
0.7321	Intermediate Similarity	NPD9615	Approved
0.7321	Intermediate Similarity	NPD9613	Approved
0.7315	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD9089	Approved
0.7281	Intermediate Similarity	NPD3095	Discontinued
0.7281	Intermediate Similarity	NPD4626	Approved
0.7281	Intermediate Similarity	NPD4589	Approved
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7273	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5303	Approved
0.7257	Intermediate Similarity	NPD5304	Approved
0.7257	Intermediate Similarity	NPD316	Approved
0.7241	Intermediate Similarity	NPD2232	Approved
0.7241	Intermediate Similarity	NPD2230	Approved
0.7241	Intermediate Similarity	NPD2233	Approved
0.7232	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1983	Approved
0.7217	Intermediate Similarity	NPD1980	Approved
0.7217	Intermediate Similarity	NPD1981	Approved
0.7207	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD9093	Approved
0.7203	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3094	Phase 2
0.7182	Intermediate Similarity	NPD7843	Approved
0.7179	Intermediate Similarity	NPD1755	Approved
0.7179	Intermediate Similarity	NPD4749	Approved
0.7155	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD2194	Approved
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD255	Approved
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD2195	Approved
0.7143	Intermediate Similarity	NPD256	Approved
0.7143	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD9384	Approved
0.713	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD9381	Approved
0.7119	Intermediate Similarity	NPD5311	Approved
0.7119	Intermediate Similarity	NPD5310	Approved
0.7094	Intermediate Similarity	NPD2235	Phase 2
0.7094	Intermediate Similarity	NPD2231	Phase 2
0.7083	Intermediate Similarity	NPD3637	Approved
0.7083	Intermediate Similarity	NPD9073	Approved
0.7083	Intermediate Similarity	NPD5736	Approved
0.7083	Intermediate Similarity	NPD2861	Phase 2
0.7083	Intermediate Similarity	NPD3635	Approved
0.7083	Intermediate Similarity	NPD3636	Approved
0.708	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD9244	Approved
0.7069	Intermediate Similarity	NPD3496	Discontinued
0.7064	Intermediate Similarity	NPD5451	Approved
0.7059	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD3055	Approved
0.7054	Intermediate Similarity	NPD475	Phase 2
0.7054	Intermediate Similarity	NPD497	Approved
0.7048	Intermediate Similarity	NPD4817	Approved
0.7048	Intermediate Similarity	NPD4818	Approved
0.7037	Intermediate Similarity	NPD290	Approved
0.7037	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD821	Approved
0.7025	Intermediate Similarity	NPD3594	Approved
0.7025	Intermediate Similarity	NPD2605	Approved
0.7025	Intermediate Similarity	NPD3595	Approved
0.7025	Intermediate Similarity	NPD2606	Approved
0.7018	Intermediate Similarity	NPD856	Approved
0.7018	Intermediate Similarity	NPD16	Approved
0.6991	Remote Similarity	NPD709	Approved
0.6983	Remote Similarity	NPD2668	Approved
0.6983	Remote Similarity	NPD2667	Approved
0.6981	Remote Similarity	NPD3680	Approved
0.6981	Remote Similarity	NPD4658	Approved
0.6981	Remote Similarity	NPD3682	Approved
0.6981	Remote Similarity	NPD4231	Approved
0.6981	Remote Similarity	NPD3683	Approved
0.6981	Remote Similarity	NPD3681	Approved
0.6981	Remote Similarity	NPD4229	Approved
0.6981	Remote Similarity	NPD4656	Approved
0.6975	Remote Similarity	NPD6696	Suspended
0.6972	Remote Similarity	NPD74	Approved
0.6972	Remote Similarity	NPD9266	Approved
0.697	Remote Similarity	NPD9295	Approved
0.6967	Remote Similarity	NPD4625	Phase 3
0.6967	Remote Similarity	NPD5156	Approved
0.6967	Remote Similarity	NPD3027	Phase 3
0.6967	Remote Similarity	NPD5155	Approved
0.6964	Remote Similarity	NPD496	Approved
0.6964	Remote Similarity	NPD498	Approved
0.6964	Remote Similarity	NPD495	Approved
0.6957	Remote Similarity	NPD1759	Phase 1
0.6957	Remote Similarity	NPD7330	Discontinued
0.6952	Remote Similarity	NPD1616	Discontinued
0.6931	Remote Similarity	NPD159	Clinical (unspecified phase)
0.693	Remote Similarity	NPD9568	Approved
0.6923	Remote Similarity	NPD3023	Approved
0.6923	Remote Similarity	NPD3026	Approved
0.6917	Remote Similarity	NPD1470	Approved
0.6911	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3024	Approved
0.6897	Remote Similarity	NPD5691	Approved
0.6897	Remote Similarity	NPD3025	Approved
0.6897	Remote Similarity	NPD1357	Approved
0.6891	Remote Similarity	NPD6583	Phase 3
0.6891	Remote Similarity	NPD9622	Approved
0.6891	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4659	Approved
0.6891	Remote Similarity	NPD6582	Phase 2
0.6881	Remote Similarity	NPD9263	Approved
0.6881	Remote Similarity	NPD9264	Approved
0.6881	Remote Similarity	NPD9267	Approved
0.6875	Remote Similarity	NPD5535	Approved
0.687	Remote Similarity	NPD317	Approved
0.687	Remote Similarity	NPD318	Approved
0.687	Remote Similarity	NPD1758	Phase 1
0.6869	Remote Similarity	NPD9094	Approved
0.6864	Remote Similarity	NPD1610	Phase 2
0.686	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.686	Remote Similarity	NPD257	Approved
0.686	Remote Similarity	NPD4624	Approved
0.686	Remote Similarity	NPD258	Approved
0.6855	Remote Similarity	NPD6663	Approved
0.6838	Remote Similarity	NPD1778	Approved
0.6833	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4717	Approved
0.6818	Remote Similarity	NPD4718	Approved
0.6818	Remote Similarity	NPD4720	Approved
0.6814	Remote Similarity	NPD1398	Phase 1
0.681	Remote Similarity	NPD1548	Phase 1
0.6807	Remote Similarity	NPD2562	Approved
0.6807	Remote Similarity	NPD2561	Approved
0.6807	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1608	Approved
0.68	Remote Similarity	NPD4060	Phase 1
0.68	Remote Similarity	NPD6346	Approved
0.6789	Remote Similarity	NPD3134	Approved
0.6783	Remote Similarity	NPD7636	Approved
0.6783	Remote Similarity	NPD7340	Approved
0.6783	Remote Similarity	NPD9493	Approved
0.678	Remote Similarity	NPD3847	Discontinued
0.678	Remote Similarity	NPD3143	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