NPASS Compound

Structure

CID293831 OpenBabel06191716102D 24 26 0 0 1 0 0 0 0 0999 V2000 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 1.1340 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 -0.5000 0.8660 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 4.3301 1.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 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 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 6 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	2.538
LogD:	1.647
LogS:	-3.446
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	3.986
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.957
MDCK Permeability:	2.1978599761496298e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.743
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.304
Plasma Protein Binding (PPB):	79.99748229980469%
Volume Distribution (VD):	0.433
Pgp-substrate:	20.703571319580078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.655
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.387
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	1.319
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.452
Carcinogencity:	0.077
Eye Corrosion:	0.005
Eye Irritation:	0.144
Respiratory Toxicity:	0.194

Download Data

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

Natural Product: NPC293831

Natural Product ID:	NPC293831
*Common Name:**	7Beta,15-Dihydroxydehydroabietic Acid
IUPAC Name:	(1R,4aS,9S,10aR)-9-hydroxy-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
Synonyms:	7Beta,15-Dihydroxydehydroabietic Acid
Standard InCHIKey:	ALGYTGOYQATWBA-LNKGRISISA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-18(2,24)12-6-7-14-13(10-12)15(21)11-16-19(14,3)8-5-9-20(16,4)17(22)23/h6-7,10,15-16,21,24H,5,8-9,11H2,1-4H3,(H,22,23)/p-1/t15-,16+,19+,20+/m0/s1
SMILES:	CC(C)(c1ccc2c(c1)[C@H](C[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)[O-])O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL604673
PubChem CID:	21626423
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO2882	Abies georgei	Species	Pinaceae	Eukaryota	aerial parts	Zhongdian city, Yunnan Province of China	n.a.	PMID[20022253]
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[32633512]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20154	Cedrus atlantica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20154	Cedrus atlantica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5205	Gymnoascus reesii	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9311	Parkia clappertoniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10588	Diploschistes violarius	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10177	Eria linearifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9051	Delesseria sanguinea	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO822	Cressa cretica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11832	Pinus banksiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12895	Polypodiodes niponica	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12322	Amomum krervanh	Species	Zingiberaceae	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	4
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[525721]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[525721]
NPT737	Cell Line	HUVEC	Homo sapiens	Activity	=	8.95	%	PMID[525722]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[525721]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[525721]

☑ 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 NPC293831 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	217
0.1-0.2	954
0.2-0.3	2082
0.3-0.4	4887
0.4-0.5	9694
0.5-0.6	15693
0.6-0.7	7985
0.7-0.8	1105
0.8-0.85	48
0.85-0.9	25
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC369
0.9825	High Similarity	NPC183339
0.9825	High Similarity	NPC234337
0.9825	High Similarity	NPC133389
0.958	High Similarity	NPC253681
0.9138	High Similarity	NPC212891
0.9008	High Similarity	NPC77691
0.8947	High Similarity	NPC95126
0.8947	High Similarity	NPC475002
0.8926	High Similarity	NPC273336
0.8926	High Similarity	NPC182333
0.887	High Similarity	NPC471188
0.879	High Similarity	NPC5486
0.8772	High Similarity	NPC472982
0.8772	High Similarity	NPC64642
0.8772	High Similarity	NPC149455
0.8684	High Similarity	NPC27252
0.8684	High Similarity	NPC472979
0.8644	High Similarity	NPC221275
0.8607	High Similarity	NPC472981
0.8596	High Similarity	NPC94751
0.8596	High Similarity	NPC142326
0.8583	High Similarity	NPC45794
0.8548	High Similarity	NPC307139
0.8548	High Similarity	NPC85511
0.8547	High Similarity	NPC471189
0.8537	High Similarity	NPC167323
0.8537	High Similarity	NPC269923
0.8522	High Similarity	NPC472980
0.8509	High Similarity	NPC243601
0.85	High Similarity	NPC105141
0.85	High Similarity	NPC242764
0.8462	Intermediate Similarity	NPC133308
0.845	Intermediate Similarity	NPC476847
0.8425	Intermediate Similarity	NPC51448
0.8425	Intermediate Similarity	NPC115797
0.8348	Intermediate Similarity	NPC471186
0.8347	Intermediate Similarity	NPC472862
0.8333	Intermediate Similarity	NPC19856
0.8333	Intermediate Similarity	NPC186933
0.8321	Intermediate Similarity	NPC49742
0.8296	Intermediate Similarity	NPC3218
0.8293	Intermediate Similarity	NPC476645
0.8268	Intermediate Similarity	NPC87985
0.8268	Intermediate Similarity	NPC275576
0.8258	Intermediate Similarity	NPC477893
0.8258	Intermediate Similarity	NPC477896
0.824	Intermediate Similarity	NPC162935
0.824	Intermediate Similarity	NPC249340
0.8235	Intermediate Similarity	NPC272907
0.8235	Intermediate Similarity	NPC2681
0.8211	Intermediate Similarity	NPC254233
0.8203	Intermediate Similarity	NPC169913
0.8189	Intermediate Similarity	NPC181334
0.8182	Intermediate Similarity	NPC310662
0.8175	Intermediate Similarity	NPC121168
0.816	Intermediate Similarity	NPC241001
0.8158	Intermediate Similarity	NPC136810
0.8158	Intermediate Similarity	NPC469481
0.8158	Intermediate Similarity	NPC128248
0.8158	Intermediate Similarity	NPC225079
0.8158	Intermediate Similarity	NPC133809
0.8148	Intermediate Similarity	NPC79921
0.8145	Intermediate Similarity	NPC42657
0.8125	Intermediate Similarity	NPC137750
0.812	Intermediate Similarity	NPC293454
0.812	Intermediate Similarity	NPC471864
0.811	Intermediate Similarity	NPC471187
0.811	Intermediate Similarity	NPC140118
0.811	Intermediate Similarity	NPC12881
0.8102	Intermediate Similarity	NPC477894
0.8074	Intermediate Similarity	NPC477592
0.8062	Intermediate Similarity	NPC470753
0.8062	Intermediate Similarity	NPC473220
0.806	Intermediate Similarity	NPC279463
0.8058	Intermediate Similarity	NPC126707
0.8045	Intermediate Similarity	NPC48929
0.8045	Intermediate Similarity	NPC126516
0.8031	Intermediate Similarity	NPC11250
0.8029	Intermediate Similarity	NPC172311
0.8016	Intermediate Similarity	NPC164852
0.8	Intermediate Similarity	NPC262324
0.7985	Intermediate Similarity	NPC23894
0.7985	Intermediate Similarity	NPC213122
0.7985	Intermediate Similarity	NPC202225
0.7984	Intermediate Similarity	NPC470816
0.7984	Intermediate Similarity	NPC470765
0.7969	Intermediate Similarity	NPC198014
0.7955	Intermediate Similarity	NPC72915
0.7953	Intermediate Similarity	NPC253627
0.7949	Intermediate Similarity	NPC472221
0.7949	Intermediate Similarity	NPC472222
0.7943	Intermediate Similarity	NPC474991
0.7939	Intermediate Similarity	NPC229894
0.7937	Intermediate Similarity	NPC478121
0.7934	Intermediate Similarity	NPC111108
0.7926	Intermediate Similarity	NPC472374
0.7926	Intermediate Similarity	NPC472372
0.792	Intermediate Similarity	NPC471671
0.7913	Intermediate Similarity	NPC221825
0.791	Intermediate Similarity	NPC78307
0.791	Intermediate Similarity	NPC475346
0.791	Intermediate Similarity	NPC475457
0.791	Intermediate Similarity	NPC329913
0.791	Intermediate Similarity	NPC475627
0.791	Intermediate Similarity	NPC18982
0.7903	Intermediate Similarity	NPC470820
0.7903	Intermediate Similarity	NPC92
0.7903	Intermediate Similarity	NPC469663
0.7895	Intermediate Similarity	NPC471851
0.7895	Intermediate Similarity	NPC18798
0.7895	Intermediate Similarity	NPC324602
0.7883	Intermediate Similarity	NPC100913
0.7883	Intermediate Similarity	NPC477593
0.7883	Intermediate Similarity	NPC275592
0.7883	Intermediate Similarity	NPC90614
0.7879	Intermediate Similarity	NPC49272
0.7879	Intermediate Similarity	NPC147561
0.7879	Intermediate Similarity	NPC117899
0.7879	Intermediate Similarity	NPC131684
0.7874	Intermediate Similarity	NPC32322
0.7874	Intermediate Similarity	NPC259703
0.7868	Intermediate Similarity	NPC243893
0.7868	Intermediate Similarity	NPC39549
0.7863	Intermediate Similarity	NPC30491
0.7863	Intermediate Similarity	NPC262936
0.7857	Intermediate Similarity	NPC469644
0.7857	Intermediate Similarity	NPC477207
0.7852	Intermediate Similarity	NPC194970
0.7852	Intermediate Similarity	NPC477594
0.7851	Intermediate Similarity	NPC265513
0.7846	Intermediate Similarity	NPC9180
0.7846	Intermediate Similarity	NPC100402
0.7842	Intermediate Similarity	NPC91703
0.784	Intermediate Similarity	NPC172219
0.784	Intermediate Similarity	NPC304510
0.7833	Intermediate Similarity	NPC475006
0.7826	Intermediate Similarity	NPC97947
0.7826	Intermediate Similarity	NPC291599
0.7826	Intermediate Similarity	NPC27377
0.7826	Intermediate Similarity	NPC118080
0.7826	Intermediate Similarity	NPC87448
0.7826	Intermediate Similarity	NPC472576
0.7826	Intermediate Similarity	NPC41481
0.7823	Intermediate Similarity	NPC9274
0.7817	Intermediate Similarity	NPC191899
0.7817	Intermediate Similarity	NPC246229
0.781	Intermediate Similarity	NPC475957
0.7805	Intermediate Similarity	NPC196673
0.7805	Intermediate Similarity	NPC471721
0.7803	Intermediate Similarity	NPC193203
0.7794	Intermediate Similarity	NPC472545
0.7794	Intermediate Similarity	NPC472804
0.7794	Intermediate Similarity	NPC477596
0.7794	Intermediate Similarity	NPC472551
0.7787	Intermediate Similarity	NPC66208
0.7786	Intermediate Similarity	NPC248068
0.7778	Intermediate Similarity	NPC469609
0.7778	Intermediate Similarity	NPC203486
0.777	Intermediate Similarity	NPC471853
0.777	Intermediate Similarity	NPC182869
0.7762	Intermediate Similarity	NPC5568
0.7762	Intermediate Similarity	NPC127046
0.7761	Intermediate Similarity	NPC291001
0.776	Intermediate Similarity	NPC308311
0.776	Intermediate Similarity	NPC477137
0.776	Intermediate Similarity	NPC158157
0.776	Intermediate Similarity	NPC219112
0.776	Intermediate Similarity	NPC38893
0.7754	Intermediate Similarity	NPC97667
0.7754	Intermediate Similarity	NPC171207
0.7754	Intermediate Similarity	NPC472547
0.7754	Intermediate Similarity	NPC476643
0.7752	Intermediate Similarity	NPC478058
0.7752	Intermediate Similarity	NPC176208
0.7752	Intermediate Similarity	NPC108286
0.775	Intermediate Similarity	NPC21929
0.7746	Intermediate Similarity	NPC84786
0.7744	Intermediate Similarity	NPC276238
0.7744	Intermediate Similarity	NPC472388
0.7744	Intermediate Similarity	NPC82712
0.7744	Intermediate Similarity	NPC262819
0.7742	Intermediate Similarity	NPC93181
0.7739	Intermediate Similarity	NPC226041
0.7737	Intermediate Similarity	NPC249817
0.773	Intermediate Similarity	NPC127857
0.773	Intermediate Similarity	NPC472556
0.7727	Intermediate Similarity	NPC176130
0.7727	Intermediate Similarity	NPC78364
0.7727	Intermediate Similarity	NPC69424
0.7727	Intermediate Similarity	NPC84672
0.7724	Intermediate Similarity	NPC93287
0.7721	Intermediate Similarity	NPC474659
0.7717	Intermediate Similarity	NPC202015
0.7714	Intermediate Similarity	NPC163087
0.7714	Intermediate Similarity	NPC477595
0.771	Intermediate Similarity	NPC470649
0.771	Intermediate Similarity	NPC478107
0.771	Intermediate Similarity	NPC137416
0.7708	Intermediate Similarity	NPC477206

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 NPC293831 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	716
0.2-0.3	1331
0.3-0.4	2607
0.4-0.5	2316
0.5-0.6	1475
0.6-0.7	453
0.7-0.8	41
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD5951	Approved
0.8033	Intermediate Similarity	NPD2629	Approved
0.7795	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD6663	Approved
0.7744	Intermediate Similarity	NPD7008	Discontinued
0.7744	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5736	Approved
0.768	Intermediate Similarity	NPD4198	Discontinued
0.7661	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3019	Approved
0.763	Intermediate Similarity	NPD7714	Approved
0.763	Intermediate Similarity	NPD7715	Approved
0.7606	Intermediate Similarity	NPD7236	Approved
0.7583	Intermediate Similarity	NPD5048	Discontinued
0.7563	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD3317	Approved
0.7519	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD7741	Discontinued
0.7466	Intermediate Similarity	NPD7239	Suspended
0.7419	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1088	Approved
0.7381	Intermediate Similarity	NPD6010	Discontinued
0.7379	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD3091	Approved
0.7357	Intermediate Similarity	NPD7305	Phase 1
0.7328	Intermediate Similarity	NPD3023	Approved
0.7328	Intermediate Similarity	NPD3026	Approved
0.7311	Intermediate Similarity	NPD2066	Phase 3
0.7308	Intermediate Similarity	NPD3025	Approved
0.7308	Intermediate Similarity	NPD3024	Approved
0.7305	Intermediate Similarity	NPD5405	Approved
0.7305	Intermediate Similarity	NPD5404	Approved
0.7305	Intermediate Similarity	NPD5406	Approved
0.7305	Intermediate Similarity	NPD5408	Approved
0.7273	Intermediate Similarity	NPD3092	Approved
0.7265	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD3095	Discontinued
0.7252	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1283	Approved
0.7227	Intermediate Similarity	NPD9495	Approved
0.7222	Intermediate Similarity	NPD7003	Approved
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7217	Intermediate Similarity	NPD1086	Approved
0.7217	Intermediate Similarity	NPD1090	Approved
0.7217	Intermediate Similarity	NPD1089	Approved
0.7185	Intermediate Similarity	NPD3094	Phase 2
0.7165	Intermediate Similarity	NPD6858	Approved
0.7165	Intermediate Similarity	NPD7094	Approved
0.7131	Intermediate Similarity	NPD1930	Approved
0.7131	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD1929	Approved
0.713	Intermediate Similarity	NPD800	Approved
0.7121	Intermediate Similarity	NPD5125	Phase 3
0.7121	Intermediate Similarity	NPD5126	Approved
0.7119	Intermediate Similarity	NPD1693	Approved
0.7103	Intermediate Similarity	NPD8166	Discontinued
0.7071	Intermediate Similarity	NPD4140	Approved
0.7067	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD1989	Approved
0.7034	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7610	Discontinued
0.7015	Intermediate Similarity	NPD1201	Approved
0.7015	Intermediate Similarity	NPD1281	Approved
0.7013	Intermediate Similarity	NPD7058	Phase 2
0.7013	Intermediate Similarity	NPD7057	Phase 3
0.7009	Intermediate Similarity	NPD1239	Approved
0.7007	Intermediate Similarity	NPD6085	Phase 2
0.7007	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1564	Approved
0.7	Intermediate Similarity	NPD1566	Phase 3
0.7	Intermediate Similarity	NPD7961	Discontinued
0.7	Intermediate Similarity	NPD1565	Approved
0.6993	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5305	Approved
0.6992	Remote Similarity	NPD6647	Phase 2
0.6992	Remote Similarity	NPD5306	Approved
0.6992	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4199	Phase 3
0.6992	Remote Similarity	NPD5765	Approved
0.698	Remote Similarity	NPD6273	Approved
0.6975	Remote Similarity	NPD6049	Phase 2
0.6975	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.696	Remote Similarity	NPD6685	Approved
0.6957	Remote Similarity	NPD1087	Approved
0.6954	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2979	Phase 3
0.6944	Remote Similarity	NPD6099	Approved
0.6944	Remote Similarity	NPD6100	Approved
0.6939	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7799	Discontinued
0.6935	Remote Similarity	NPD5909	Discontinued
0.6935	Remote Similarity	NPD1237	Approved
0.6934	Remote Similarity	NPD1470	Approved
0.6929	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD37	Approved
0.6918	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2342	Discontinued
0.6899	Remote Similarity	NPD7635	Approved
0.6889	Remote Similarity	NPD4807	Approved
0.6889	Remote Similarity	NPD4806	Approved
0.6879	Remote Similarity	NPD8032	Phase 2
0.6875	Remote Similarity	NPD7033	Discontinued
0.6875	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7725	Approved
0.6866	Remote Similarity	NPD4059	Approved
0.6866	Remote Similarity	NPD4626	Approved
0.6846	Remote Similarity	NPD7390	Discontinued
0.6842	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1608	Approved
0.6828	Remote Similarity	NPD2438	Suspended
0.6815	Remote Similarity	NPD4135	Approved
0.6815	Remote Similarity	NPD4136	Approved
0.6815	Remote Similarity	NPD4106	Approved
0.6795	Remote Similarity	NPD4965	Approved
0.6795	Remote Similarity	NPD4966	Approved
0.6795	Remote Similarity	NPD4967	Phase 2
0.6791	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1651	Approved
0.679	Remote Similarity	NPD5844	Phase 1
0.6781	Remote Similarity	NPD6002	Phase 3
0.6781	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6005	Phase 3
0.6781	Remote Similarity	NPD6004	Phase 3
0.6765	Remote Similarity	NPD5618	Discontinued
0.6759	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3400	Discontinued
0.675	Remote Similarity	NPD1563	Approved
0.6748	Remote Similarity	NPD7798	Approved
0.6741	Remote Similarity	NPD1778	Approved
0.6732	Remote Similarity	NPD3226	Approved
0.673	Remote Similarity	NPD8127	Discontinued
0.6721	Remote Similarity	NPD3495	Discontinued
0.6719	Remote Similarity	NPD2182	Approved
0.6715	Remote Similarity	NPD4878	Approved
0.6713	Remote Similarity	NPD4060	Phase 1
0.6712	Remote Similarity	NPD2531	Phase 2
0.6711	Remote Similarity	NPD6190	Approved
0.6695	Remote Similarity	NPD5347	Phase 2
0.6695	Remote Similarity	NPD5346	Phase 2
0.669	Remote Similarity	NPD6798	Discontinued
0.669	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2534	Approved
0.6689	Remote Similarity	NPD2532	Approved
0.6689	Remote Similarity	NPD2533	Approved
0.6687	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD4617	Approved
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD4105	Approved
0.6667	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5203	Approved
0.6667	Remote Similarity	NPD5201	Approved
0.6667	Remote Similarity	NPD4620	Approved
0.6667	Remote Similarity	NPD4102	Approved
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4110	Phase 3
0.6642	Remote Similarity	NPD6287	Discontinued
0.664	Remote Similarity	NPD1932	Approved
0.6639	Remote Similarity	NPD3672	Approved
0.6639	Remote Similarity	NPD3673	Approved
0.662	Remote Similarity	NPD6966	Discovery
0.662	Remote Similarity	NPD7095	Approved
0.6618	Remote Similarity	NPD17	Approved
0.6613	Remote Similarity	NPD3020	Approved
0.6609	Remote Similarity	NPD9491	Approved
0.6604	Remote Similarity	NPD6234	Discontinued
0.6599	Remote Similarity	NPD4477	Approved
0.6599	Remote Similarity	NPD4476	Approved
0.6597	Remote Similarity	NPD5119	Approved
0.6597	Remote Similarity	NPD5121	Approved
0.6597	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5120	Approved
0.6596	Remote Similarity	NPD5204	Approved
0.6593	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD9545	Approved
0.6593	Remote Similarity	NPD7009	Phase 2
0.6589	Remote Similarity	NPD2329	Discontinued
0.6584	Remote Similarity	NPD7229	Phase 3
0.6579	Remote Similarity	NPD226	Approved
0.6573	Remote Similarity	NPD3268	Approved
0.6573	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2797	Approved
0.6569	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD8150	Discontinued
0.6567	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8368	Discontinued
0.6565	Remote Similarity	NPD6912	Phase 3
0.6565	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5735	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