NPASS Compound

Structure

CID234337 OpenBabel06191716032D 23 25 0 0 1 0 0 0 0 0999 V2000 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 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 2.5981 -3.5000 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 0.0000 -2.0000 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 3.4641 -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 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 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 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 -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 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 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 12 1 0 0 0 0 2 12 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 13 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 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:	316.2
Volume:	344.632
LogP:	3.885
LogD:	3.139
LogS:	-3.654
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.85
Synthetic Accessibility Score:	3.837
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.818
MDCK Permeability:	2.328053415112663e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.332
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.847
30% Bioavailability (F30%):	0.666

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	94.7291030883789%
Volume Distribution (VD):	0.314
Pgp-substrate:	7.054370880126953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.617
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	1.004
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.646
Carcinogencity:	0.069
Eye Corrosion:	0.017
Eye Irritation:	0.582
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC234337

Natural Product ID:	NPC234337
*Common Name:**	7Beta-Hydroxydehydroabietic Acid
IUPAC Name:	(1R,4aS,9S,10aR)-9-hydroxy-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
Synonyms:	7Beta-Hydroxydehydroabietic Acid
Standard InCHIKey:	GPFVBJYXFRIOFB-ONCXSQPRSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12(2)13-6-7-15-14(10-13)16(21)11-17-19(15,3)8-5-9-20(17,4)18(22)23/h6-7,10,12,16-17,21H,5,8-9,11H2,1-4H3,(H,22,23)/t16-,17+,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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL604787
PubChem CID:	13370052
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]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	trunk	n.a.	n.a.	PMID[24224862]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	Trunk	n.a.	n.a.	PMID[26812172]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30063340]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32100544]
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[32633512]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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[TCMID]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4144	Scutia buxifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO10177	Eria linearifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12422	Pinus massoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10588	Diploschistes violarius	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3102	Arachniodes exilis	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9051	Delesseria sanguinea	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO822	Cressa cretica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9522	Pericopsis angolensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3762	Amentotaxus argotaenia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29383	Abies holophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12322	Amomum krervanh	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11832	Pinus banksiana	Species	Pinaceae	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]

☑ 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	9
Others	2

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	3
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[558878]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[558878]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	165.1	%	PMID[558879]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	96.2	%	PMID[558879]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[558879]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[558879]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	17900.0	nM	PMID[558880]
NPT2	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[558878]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[558878]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[558879]

☑ 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 NPC234337 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	212
0.1-0.2	966
0.2-0.3	2060
0.3-0.4	5105
0.4-0.5	10057
0.5-0.6	15834
0.6-0.7	7391
0.7-0.8	984
0.8-0.85	58
0.85-0.9	23
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133389
1.0	High Similarity	NPC183339
0.9825	High Similarity	NPC369
0.9825	High Similarity	NPC293831
0.9412	High Similarity	NPC253681
0.9027	High Similarity	NPC471188
0.8966	High Similarity	NPC212891
0.8938	High Similarity	NPC475002
0.8938	High Similarity	NPC95126
0.8929	High Similarity	NPC149455
0.8929	High Similarity	NPC64642
0.8929	High Similarity	NPC472982
0.8917	High Similarity	NPC273336
0.8917	High Similarity	NPC182333
0.8843	High Similarity	NPC77691
0.875	High Similarity	NPC94751
0.875	High Similarity	NPC142326
0.8696	High Similarity	NPC471189
0.8673	High Similarity	NPC27252
0.8673	High Similarity	NPC472979
0.8661	High Similarity	NPC243601
0.8632	High Similarity	NPC221275
0.8629	High Similarity	NPC5486
0.8595	High Similarity	NPC472981
0.8583	High Similarity	NPC476847
0.8571	High Similarity	NPC45794
0.8537	High Similarity	NPC307139
0.8509	High Similarity	NPC472980
0.8496	Intermediate Similarity	NPC471186
0.845	Intermediate Similarity	NPC49742
0.843	Intermediate Similarity	NPC476645
0.84	Intermediate Similarity	NPC87985
0.8387	Intermediate Similarity	NPC85511
0.8374	Intermediate Similarity	NPC162935
0.8374	Intermediate Similarity	NPC249340
0.8374	Intermediate Similarity	NPC269923
0.8374	Intermediate Similarity	NPC167323
0.8333	Intermediate Similarity	NPC242764
0.8333	Intermediate Similarity	NPC105141
0.8333	Intermediate Similarity	NPC472862
0.832	Intermediate Similarity	NPC181334
0.8319	Intermediate Similarity	NPC19856
0.8319	Intermediate Similarity	NPC186933
0.8306	Intermediate Similarity	NPC121168
0.8304	Intermediate Similarity	NPC128248
0.8304	Intermediate Similarity	NPC469481
0.8304	Intermediate Similarity	NPC136810
0.8304	Intermediate Similarity	NPC133809
0.8293	Intermediate Similarity	NPC241001
0.8291	Intermediate Similarity	NPC133308
0.8284	Intermediate Similarity	NPC3218
0.8279	Intermediate Similarity	NPC42657
0.8268	Intermediate Similarity	NPC115797
0.8268	Intermediate Similarity	NPC51448
0.8254	Intermediate Similarity	NPC275576
0.8254	Intermediate Similarity	NPC137750
0.8244	Intermediate Similarity	NPC477893
0.8244	Intermediate Similarity	NPC477896
0.824	Intermediate Similarity	NPC471187
0.8222	Intermediate Similarity	NPC272907
0.8222	Intermediate Similarity	NPC2681
0.8189	Intermediate Similarity	NPC169913
0.8168	Intermediate Similarity	NPC310662
0.816	Intermediate Similarity	NPC11250
0.8142	Intermediate Similarity	NPC225079
0.8134	Intermediate Similarity	NPC79921
0.8106	Intermediate Similarity	NPC293454
0.8106	Intermediate Similarity	NPC471864
0.8106	Intermediate Similarity	NPC213122
0.8095	Intermediate Similarity	NPC198014
0.8095	Intermediate Similarity	NPC12881
0.8095	Intermediate Similarity	NPC140118
0.808	Intermediate Similarity	NPC253627
0.8077	Intermediate Similarity	NPC72915
0.8065	Intermediate Similarity	NPC478121
0.8062	Intermediate Similarity	NPC229894
0.806	Intermediate Similarity	NPC477592
0.8053	Intermediate Similarity	NPC221825
0.8049	Intermediate Similarity	NPC471671
0.8049	Intermediate Similarity	NPC254233
0.8047	Intermediate Similarity	NPC473220
0.8047	Intermediate Similarity	NPC470753
0.8043	Intermediate Similarity	NPC126707
0.8036	Intermediate Similarity	NPC324602
0.8033	Intermediate Similarity	NPC469663
0.8033	Intermediate Similarity	NPC92
0.803	Intermediate Similarity	NPC48929
0.803	Intermediate Similarity	NPC78307
0.803	Intermediate Similarity	NPC126516
0.8015	Intermediate Similarity	NPC471851
0.8015	Intermediate Similarity	NPC18798
0.8	Intermediate Similarity	NPC117899
0.8	Intermediate Similarity	NPC32322
0.8	Intermediate Similarity	NPC259703
0.8	Intermediate Similarity	NPC131684
0.7985	Intermediate Similarity	NPC262324
0.7984	Intermediate Similarity	NPC30491
0.7984	Intermediate Similarity	NPC262936
0.7984	Intermediate Similarity	NPC469644
0.7983	Intermediate Similarity	NPC265513
0.797	Intermediate Similarity	NPC23894
0.7969	Intermediate Similarity	NPC470816
0.7969	Intermediate Similarity	NPC470765
0.7967	Intermediate Similarity	NPC304510
0.7967	Intermediate Similarity	NPC172219
0.7956	Intermediate Similarity	NPC477894
0.7934	Intermediate Similarity	NPC196673
0.7934	Intermediate Similarity	NPC471721
0.7931	Intermediate Similarity	NPC472221
0.7931	Intermediate Similarity	NPC472222
0.7929	Intermediate Similarity	NPC474991
0.7923	Intermediate Similarity	NPC193203
0.7917	Intermediate Similarity	NPC111108
0.7917	Intermediate Similarity	NPC66208
0.791	Intermediate Similarity	NPC472374
0.791	Intermediate Similarity	NPC472372
0.791	Intermediate Similarity	NPC279463
0.7903	Intermediate Similarity	NPC469609
0.7895	Intermediate Similarity	NPC475346
0.7895	Intermediate Similarity	NPC18982
0.7895	Intermediate Similarity	NPC475457
0.7895	Intermediate Similarity	NPC475627
0.7895	Intermediate Similarity	NPC329913
0.7886	Intermediate Similarity	NPC470820
0.7886	Intermediate Similarity	NPC308311
0.7886	Intermediate Similarity	NPC219112
0.7886	Intermediate Similarity	NPC38893
0.7886	Intermediate Similarity	NPC477137
0.7883	Intermediate Similarity	NPC172311
0.7879	Intermediate Similarity	NPC291001
0.7876	Intermediate Similarity	NPC226041
0.7874	Intermediate Similarity	NPC176208
0.7874	Intermediate Similarity	NPC478058
0.7868	Intermediate Similarity	NPC477593
0.7863	Intermediate Similarity	NPC276238
0.7863	Intermediate Similarity	NPC82712
0.7857	Intermediate Similarity	NPC164852
0.7852	Intermediate Similarity	NPC243893
0.7851	Intermediate Similarity	NPC93287
0.7846	Intermediate Similarity	NPC176130
0.7846	Intermediate Similarity	NPC69424
0.7846	Intermediate Similarity	NPC78364
0.7846	Intermediate Similarity	NPC84672
0.7842	Intermediate Similarity	NPC477207
0.7836	Intermediate Similarity	NPC194970
0.7836	Intermediate Similarity	NPC202225
0.7836	Intermediate Similarity	NPC477594
0.7829	Intermediate Similarity	NPC100402
0.7829	Intermediate Similarity	NPC9180
0.7823	Intermediate Similarity	NPC477136
0.782	Intermediate Similarity	NPC165612
0.7805	Intermediate Similarity	NPC35797
0.7805	Intermediate Similarity	NPC9274
0.7805	Intermediate Similarity	NPC192948
0.7805	Intermediate Similarity	NPC147179
0.7801	Intermediate Similarity	NPC246229
0.7801	Intermediate Similarity	NPC191899
0.7795	Intermediate Similarity	NPC154696
0.7794	Intermediate Similarity	NPC475957
0.7786	Intermediate Similarity	NPC3009
0.7778	Intermediate Similarity	NPC318552
0.7778	Intermediate Similarity	NPC472804
0.7778	Intermediate Similarity	NPC190501
0.7778	Intermediate Similarity	NPC477596
0.7778	Intermediate Similarity	NPC56168
0.777	Intermediate Similarity	NPC248068
0.7769	Intermediate Similarity	NPC71610
0.7769	Intermediate Similarity	NPC269598
0.7761	Intermediate Similarity	NPC203486
0.7761	Intermediate Similarity	NPC477139
0.776	Intermediate Similarity	NPC328694
0.776	Intermediate Similarity	NPC154030
0.7754	Intermediate Similarity	NPC471853
0.7754	Intermediate Similarity	NPC182869
0.7746	Intermediate Similarity	NPC5568
0.7746	Intermediate Similarity	NPC127046
0.7742	Intermediate Similarity	NPC308828
0.7742	Intermediate Similarity	NPC158157
0.7737	Intermediate Similarity	NPC90614
0.7737	Intermediate Similarity	NPC100913
0.7737	Intermediate Similarity	NPC275592
0.7737	Intermediate Similarity	NPC476643
0.7731	Intermediate Similarity	NPC21929
0.773	Intermediate Similarity	NPC84786
0.7727	Intermediate Similarity	NPC49272
0.7727	Intermediate Similarity	NPC472388
0.7727	Intermediate Similarity	NPC147561
0.7724	Intermediate Similarity	NPC268160
0.7724	Intermediate Similarity	NPC93181
0.7724	Intermediate Similarity	NPC215419
0.7721	Intermediate Similarity	NPC249817
0.7721	Intermediate Similarity	NPC39549
0.7717	Intermediate Similarity	NPC328504
0.771	Intermediate Similarity	NPC72667
0.7704	Intermediate Similarity	NPC474659
0.7698	Intermediate Similarity	NPC477595
0.7698	Intermediate Similarity	NPC91703
0.7698	Intermediate Similarity	NPC202015
0.7692	Intermediate Similarity	NPC137416
0.7681	Intermediate Similarity	NPC291599

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 NPC234337 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	739
0.2-0.3	1270
0.3-0.4	2650
0.4-0.5	2319
0.5-0.6	1468
0.6-0.7	443
0.7-0.8	50
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8319	Intermediate Similarity	NPD5951	Approved
0.8167	Intermediate Similarity	NPD2629	Approved
0.792	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6663	Approved
0.7863	Intermediate Similarity	NPD7008	Discontinued
0.7846	Intermediate Similarity	NPD5736	Approved
0.7778	Intermediate Similarity	NPD3019	Approved
0.7727	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2932	Approved
0.7563	Intermediate Similarity	NPD5048	Discontinued
0.7522	Intermediate Similarity	NPD1088	Approved
0.7521	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD3317	Approved
0.752	Intermediate Similarity	NPD4198	Discontinued
0.75	Intermediate Similarity	NPD6010	Discontinued
0.7481	Intermediate Similarity	NPD7714	Approved
0.7481	Intermediate Similarity	NPD7715	Approved
0.748	Intermediate Similarity	NPD3091	Approved
0.7465	Intermediate Similarity	NPD7236	Approved
0.7436	Intermediate Similarity	NPD2066	Phase 3
0.7391	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3092	Approved
0.7364	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD9495	Approved
0.7348	Intermediate Similarity	NPD1283	Approved
0.7345	Intermediate Similarity	NPD1090	Approved
0.7345	Intermediate Similarity	NPD1086	Approved
0.7345	Intermediate Similarity	NPD1089	Approved
0.7344	Intermediate Similarity	NPD7741	Discontinued
0.7338	Intermediate Similarity	NPD7305	Phase 1
0.7329	Intermediate Similarity	NPD7239	Suspended
0.7324	Intermediate Similarity	NPD7003	Approved
0.7308	Intermediate Similarity	NPD3023	Approved
0.7308	Intermediate Similarity	NPD3026	Approved
0.7287	Intermediate Similarity	NPD3024	Approved
0.7287	Intermediate Similarity	NPD3025	Approved
0.7286	Intermediate Similarity	NPD5408	Approved
0.7286	Intermediate Similarity	NPD5404	Approved
0.7286	Intermediate Similarity	NPD5405	Approved
0.7286	Intermediate Similarity	NPD5406	Approved
0.728	Intermediate Similarity	NPD6858	Approved
0.728	Intermediate Similarity	NPD7094	Approved
0.7258	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD800	Approved
0.725	Intermediate Similarity	NPD1930	Approved
0.725	Intermediate Similarity	NPD1929	Approved
0.725	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1693	Approved
0.7239	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3095	Discontinued
0.7203	Intermediate Similarity	NPD4628	Phase 3
0.7179	Intermediate Similarity	NPD1989	Approved
0.7174	Intermediate Similarity	NPD4140	Approved
0.7164	Intermediate Similarity	NPD3094	Phase 2
0.713	Intermediate Similarity	NPD1239	Approved
0.7121	Intermediate Similarity	NPD1201	Approved
0.7121	Intermediate Similarity	NPD1281	Approved
0.7119	Intermediate Similarity	NPD1566	Phase 3
0.7119	Intermediate Similarity	NPD1564	Approved
0.7119	Intermediate Similarity	NPD1565	Approved
0.7099	Intermediate Similarity	NPD5126	Approved
0.7099	Intermediate Similarity	NPD5125	Phase 3
0.7094	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6049	Phase 2
0.7083	Intermediate Similarity	NPD8166	Discontinued
0.708	Intermediate Similarity	NPD1087	Approved
0.7075	Intermediate Similarity	NPD6273	Approved
0.7049	Intermediate Similarity	NPD5909	Discontinued
0.7049	Intermediate Similarity	NPD1237	Approved
0.7047	Intermediate Similarity	NPD7458	Discontinued
0.7034	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2342	Discontinued
0.7009	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD7635	Approved
0.7	Intermediate Similarity	NPD7610	Discontinued
0.6985	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6085	Phase 2
0.6984	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8032	Phase 2
0.6972	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4626	Approved
0.697	Remote Similarity	NPD5305	Approved
0.697	Remote Similarity	NPD4199	Phase 3
0.697	Remote Similarity	NPD5306	Approved
0.6967	Remote Similarity	NPD6647	Phase 2
0.6967	Remote Similarity	NPD5765	Approved
0.6967	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1608	Approved
0.6935	Remote Similarity	NPD6685	Approved
0.6933	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2979	Phase 3
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD6099	Approved
0.6912	Remote Similarity	NPD1470	Approved
0.6908	Remote Similarity	NPD37	Approved
0.6897	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1651	Approved
0.6892	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7058	Phase 2
0.6883	Remote Similarity	NPD7057	Phase 3
0.6866	Remote Similarity	NPD4806	Approved
0.6866	Remote Similarity	NPD4807	Approved
0.6864	Remote Similarity	NPD1563	Approved
0.6857	Remote Similarity	NPD7961	Discontinued
0.6842	Remote Similarity	NPD7725	Approved
0.6842	Remote Similarity	NPD1778	Approved
0.6842	Remote Similarity	NPD4059	Approved
0.6833	Remote Similarity	NPD3495	Discontinued
0.6824	Remote Similarity	NPD7390	Discontinued
0.6821	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4878	Approved
0.6813	Remote Similarity	NPD7799	Discontinued
0.681	Remote Similarity	NPD5347	Phase 2
0.681	Remote Similarity	NPD5346	Phase 2
0.6806	Remote Similarity	NPD2438	Suspended
0.6791	Remote Similarity	NPD4106	Approved
0.6791	Remote Similarity	NPD4136	Approved
0.6791	Remote Similarity	NPD4135	Approved
0.6786	Remote Similarity	NPD3764	Approved
0.6774	Remote Similarity	NPD4966	Approved
0.6774	Remote Similarity	NPD4967	Phase 2
0.6774	Remote Similarity	NPD4965	Approved
0.677	Remote Similarity	NPD5844	Phase 1
0.6767	Remote Similarity	NPD5691	Approved
0.6759	Remote Similarity	NPD6002	Phase 3
0.6759	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6004	Phase 3
0.6759	Remote Similarity	NPD6005	Phase 3
0.6759	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3672	Approved
0.6752	Remote Similarity	NPD3673	Approved
0.6748	Remote Similarity	NPD1932	Approved
0.6741	Remote Similarity	NPD5618	Discontinued
0.6736	Remote Similarity	NPD7033	Discontinued
0.6735	Remote Similarity	NPD3400	Discontinued
0.6735	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD9491	Approved
0.6721	Remote Similarity	NPD3020	Approved
0.6721	Remote Similarity	NPD7798	Approved
0.6716	Remote Similarity	NPD17	Approved
0.6714	Remote Similarity	NPD6966	Discovery
0.6711	Remote Similarity	NPD3226	Approved
0.6709	Remote Similarity	NPD8127	Discontinued
0.6696	Remote Similarity	NPD226	Approved
0.6693	Remote Similarity	NPD2182	Approved
0.6693	Remote Similarity	NPD2329	Discontinued
0.6692	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD9545	Approved
0.669	Remote Similarity	NPD2531	Phase 2
0.669	Remote Similarity	NPD4060	Phase 1
0.669	Remote Similarity	NPD4477	Approved
0.669	Remote Similarity	NPD4476	Approved
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7473	Discontinued
0.6645	Remote Similarity	NPD7819	Suspended
0.6644	Remote Similarity	NPD5763	Approved
0.6644	Remote Similarity	NPD5762	Approved
0.6644	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2346	Discontinued
0.6643	Remote Similarity	NPD4620	Approved
0.6643	Remote Similarity	NPD5201	Approved
0.6643	Remote Similarity	NPD5203	Approved
0.6643	Remote Similarity	NPD6355	Discontinued
0.6643	Remote Similarity	NPD5735	Approved
0.6643	Remote Similarity	NPD4617	Approved
0.6642	Remote Similarity	NPD4102	Approved
0.6642	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD4105	Approved
0.6641	Remote Similarity	NPD4750	Phase 3
0.6638	Remote Similarity	NPD4793	Discontinued
0.6622	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4110	Phase 3
0.6621	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6287	Discontinued
0.6617	Remote Similarity	NPD6065	Approved
0.6614	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD1809	Phase 2
0.661	Remote Similarity	NPD9256	Approved
0.661	Remote Similarity	NPD9258	Approved
0.6609	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4097	Suspended
0.6583	Remote Similarity	NPD845	Approved
0.6582	Remote Similarity	NPD6234	Discontinued
0.6579	Remote Similarity	NPD3971	Phase 1
0.6577	Remote Similarity	NPD6190	Approved
0.6573	Remote Similarity	NPD5121	Approved
0.6573	Remote Similarity	NPD5119	Approved
0.6573	Remote Similarity	NPD5120	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