NPASS Compound

Structure

CID144547 OpenBabel06191715502D 21 24 0 0 1 0 0 0 0 0999 V2000 4.5380 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -0.0219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8060 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5241 2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 9 1 0 0 0 0 5 12 2 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 0 0 0 0 9 11 2 0 0 0 0 10 2 1 1 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 12 15 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	278.09
Volume:	290.937
LogP:	5.192
LogD:	3.459
LogS:	-4.032
# Rotatable Bonds:	0
TPSA:	53.6
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.36
Synthetic Accessibility Score:	2.598
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.991
MDCK Permeability:	1.7062691767932847e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.761

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	97.81658935546875%
Volume Distribution (VD):	0.417
Pgp-substrate:	3.790710210800171%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.746
CYP2C19-inhibitor:	0.758
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.731
CYP2C9-substrate:	0.721
CYP2D6-inhibitor:	0.523
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	9.721
Half-life (T1/2):	0.426

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.527
Rat Oral Acute Toxicity:	0.84
Maximum Recommended Daily Dose:	0.861
Skin Sensitization:	0.906
Carcinogencity:	0.951
Eye Corrosion:	0.008
Eye Irritation:	0.938
Respiratory Toxicity:	0.725

Download Data

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

Natural Product: NPC144547

Natural Product ID:	NPC144547
*Common Name:**	Dihydroisotanshinone Ii
IUPAC Name:	(3S)-3,8-dimethyl-2,3-dihydronaphtho[2,1-g][1]benzofuran-4,5-dione
Synonyms:	dihydroisotanshinone ii
Standard InCHIKey:	KWKITVVBQQLHBB-SNVBAGLBSA-N
Standard InCHI:	InChI=1S/C18H14O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)18-14(10(2)8-21-18)17(20)16(13)19/h3-7,10H,8H2,1-2H3/t10-/m1/s1
SMILES:	Cc1cccc2c1ccc1c2C2=C([C@H](C)CO2)C(=O)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL227128
PubChem CID:	44425164
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO16838	Salvia glutinosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16838	Salvia glutinosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11814	Asphodeline tenuior	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16838	Salvia glutinosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11985	Glycyrrhiza triphylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11487	Senecio madagascariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13164	Iris hoogiana	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28189	Metzgeria pubescens	Species	Metzgeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14253	Bothriocline longipes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11003	Euphorbia sancta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO191	Amaranthus hybr	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	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	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[515666]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	20000.0	nM	PMID[515666]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[515666]

☑ 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 NPC144547 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	315
0.1-0.2	1417
0.2-0.3	2755
0.3-0.4	7661
0.4-0.5	12426
0.5-0.6	8657
0.6-0.7	8520
0.7-0.8	895
0.8-0.85	35
0.85-0.9	6
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC988
0.9912	High Similarity	NPC289432
0.9397	High Similarity	NPC77000
0.9397	High Similarity	NPC232958
0.9397	High Similarity	NPC238861
0.9298	High Similarity	NPC135730
0.9083	High Similarity	NPC51079
0.9043	High Similarity	NPC228936
0.9035	High Similarity	NPC13784
0.8957	High Similarity	NPC477411
0.8879	High Similarity	NPC474095
0.8803	High Similarity	NPC226093
0.8793	High Similarity	NPC196075
0.8621	High Similarity	NPC212415
0.8559	High Similarity	NPC470764
0.8462	Intermediate Similarity	NPC79496
0.8403	Intermediate Similarity	NPC474408
0.8397	Intermediate Similarity	NPC309056
0.8385	Intermediate Similarity	NPC310662
0.8376	Intermediate Similarity	NPC210089
0.8347	Intermediate Similarity	NPC228318
0.8346	Intermediate Similarity	NPC428300
0.8319	Intermediate Similarity	NPC67377
0.8308	Intermediate Similarity	NPC183103
0.8279	Intermediate Similarity	NPC318173
0.8276	Intermediate Similarity	NPC203732
0.8254	Intermediate Similarity	NPC295664
0.8175	Intermediate Similarity	NPC318067
0.8167	Intermediate Similarity	NPC241851
0.8167	Intermediate Similarity	NPC326664
0.8167	Intermediate Similarity	NPC196673
0.8136	Intermediate Similarity	NPC273837
0.812	Intermediate Similarity	NPC470391
0.8083	Intermediate Similarity	NPC128368
0.8077	Intermediate Similarity	NPC57552
0.8067	Intermediate Similarity	NPC291799
0.8067	Intermediate Similarity	NPC474057
0.8062	Intermediate Similarity	NPC478162
0.8062	Intermediate Similarity	NPC478165
0.8051	Intermediate Similarity	NPC265407
0.8051	Intermediate Similarity	NPC83628
0.8045	Intermediate Similarity	NPC212207
0.8045	Intermediate Similarity	NPC23894
0.8043	Intermediate Similarity	NPC117674
0.8034	Intermediate Similarity	NPC30594
0.8034	Intermediate Similarity	NPC37622
0.8017	Intermediate Similarity	NPC307651
0.7984	Intermediate Similarity	NPC51292
0.7984	Intermediate Similarity	NPC177925
0.797	Intermediate Similarity	NPC470406
0.7955	Intermediate Similarity	NPC279596
0.7955	Intermediate Similarity	NPC239134
0.7951	Intermediate Similarity	NPC210092
0.7949	Intermediate Similarity	NPC209632
0.7939	Intermediate Similarity	NPC471832
0.7937	Intermediate Similarity	NPC50872
0.7937	Intermediate Similarity	NPC472981
0.7923	Intermediate Similarity	NPC51448
0.7923	Intermediate Similarity	NPC115797
0.7917	Intermediate Similarity	NPC474157
0.7917	Intermediate Similarity	NPC167504
0.7917	Intermediate Similarity	NPC137315
0.791	Intermediate Similarity	NPC474659
0.7907	Intermediate Similarity	NPC476599
0.7907	Intermediate Similarity	NPC236405
0.7903	Intermediate Similarity	NPC80605
0.7903	Intermediate Similarity	NPC61651
0.7903	Intermediate Similarity	NPC323440
0.7903	Intermediate Similarity	NPC222968
0.7891	Intermediate Similarity	NPC328107
0.7883	Intermediate Similarity	NPC470407
0.7868	Intermediate Similarity	NPC186647
0.7863	Intermediate Similarity	NPC114594
0.7857	Intermediate Similarity	NPC27798
0.7857	Intermediate Similarity	NPC93241
0.7851	Intermediate Similarity	NPC270699
0.7851	Intermediate Similarity	NPC82899
0.7851	Intermediate Similarity	NPC186128
0.7851	Intermediate Similarity	NPC66208
0.7846	Intermediate Similarity	NPC474737
0.7836	Intermediate Similarity	NPC59459
0.7833	Intermediate Similarity	NPC196246
0.7833	Intermediate Similarity	NPC214067
0.7823	Intermediate Similarity	NPC190298
0.782	Intermediate Similarity	NPC164295
0.782	Intermediate Similarity	NPC477412
0.7817	Intermediate Similarity	NPC478163
0.781	Intermediate Similarity	NPC233707
0.7797	Intermediate Similarity	NPC134120
0.7794	Intermediate Similarity	NPC232996
0.7787	Intermediate Similarity	NPC143768
0.7787	Intermediate Similarity	NPC272524
0.7778	Intermediate Similarity	NPC60679
0.7778	Intermediate Similarity	NPC1249
0.7778	Intermediate Similarity	NPC204784
0.7778	Intermediate Similarity	NPC324117
0.7778	Intermediate Similarity	NPC89886
0.7769	Intermediate Similarity	NPC265513
0.7769	Intermediate Similarity	NPC305912
0.7769	Intermediate Similarity	NPC1082
0.7761	Intermediate Similarity	NPC477407
0.7761	Intermediate Similarity	NPC472656
0.776	Intermediate Similarity	NPC45794
0.7759	Intermediate Similarity	NPC70624
0.7759	Intermediate Similarity	NPC42211
0.7752	Intermediate Similarity	NPC85511
0.775	Intermediate Similarity	NPC269023
0.775	Intermediate Similarity	NPC192577
0.775	Intermediate Similarity	NPC10251
0.775	Intermediate Similarity	NPC318327
0.775	Intermediate Similarity	NPC99846
0.775	Intermediate Similarity	NPC17417
0.775	Intermediate Similarity	NPC474364
0.7746	Intermediate Similarity	NPC281398
0.7744	Intermediate Similarity	NPC27659
0.7742	Intermediate Similarity	NPC149691
0.7739	Intermediate Similarity	NPC49994
0.7737	Intermediate Similarity	NPC119542
0.7731	Intermediate Similarity	NPC119271
0.7727	Intermediate Similarity	NPC96024
0.7724	Intermediate Similarity	NPC308744
0.7721	Intermediate Similarity	NPC95485
0.7721	Intermediate Similarity	NPC88065
0.7721	Intermediate Similarity	NPC89504
0.7717	Intermediate Similarity	NPC473243
0.7717	Intermediate Similarity	NPC476225
0.7717	Intermediate Similarity	NPC105709
0.7705	Intermediate Similarity	NPC292834
0.7705	Intermediate Similarity	NPC280789
0.7704	Intermediate Similarity	NPC203486
0.7704	Intermediate Similarity	NPC329913
0.7687	Intermediate Similarity	NPC472394
0.7686	Intermediate Similarity	NPC93084
0.7686	Intermediate Similarity	NPC251854
0.768	Intermediate Similarity	NPC158157
0.7676	Intermediate Similarity	NPC478160
0.7676	Intermediate Similarity	NPC478166
0.7672	Intermediate Similarity	NPC118343
0.7672	Intermediate Similarity	NPC476042
0.7669	Intermediate Similarity	NPC131684
0.7667	Intermediate Similarity	NPC56493
0.7664	Intermediate Similarity	NPC471670
0.7661	Intermediate Similarity	NPC474685
0.7661	Intermediate Similarity	NPC221275
0.7661	Intermediate Similarity	NPC306740
0.766	Intermediate Similarity	NPC478164
0.7647	Intermediate Similarity	NPC209858
0.7647	Intermediate Similarity	NPC172483
0.7647	Intermediate Similarity	NPC274876
0.7642	Intermediate Similarity	NPC470253
0.7639	Intermediate Similarity	NPC474107
0.7638	Intermediate Similarity	NPC202015
0.7634	Intermediate Similarity	NPC328997
0.7634	Intermediate Similarity	NPC294050
0.7634	Intermediate Similarity	NPC470765
0.763	Intermediate Similarity	NPC477406
0.7627	Intermediate Similarity	NPC247976
0.7627	Intermediate Similarity	NPC301943
0.7627	Intermediate Similarity	NPC474365
0.7619	Intermediate Similarity	NPC469954
0.7615	Intermediate Similarity	NPC228739
0.7615	Intermediate Similarity	NPC182646
0.7612	Intermediate Similarity	NPC470278
0.7607	Intermediate Similarity	NPC112552
0.7606	Intermediate Similarity	NPC308006
0.7606	Intermediate Similarity	NPC245522
0.7606	Intermediate Similarity	NPC114513
0.7606	Intermediate Similarity	NPC290038
0.7597	Intermediate Similarity	NPC167323
0.7597	Intermediate Similarity	NPC269923
0.7591	Intermediate Similarity	NPC217914
0.7589	Intermediate Similarity	NPC69755
0.7586	Intermediate Similarity	NPC225060
0.7581	Intermediate Similarity	NPC153053
0.7576	Intermediate Similarity	NPC81135
0.7576	Intermediate Similarity	NPC473220
0.7576	Intermediate Similarity	NPC474264
0.7576	Intermediate Similarity	NPC470753
0.7576	Intermediate Similarity	NPC169913
0.7574	Intermediate Similarity	NPC126516
0.7568	Intermediate Similarity	NPC478161
0.7568	Intermediate Similarity	NPC478159
0.7563	Intermediate Similarity	NPC31786
0.7561	Intermediate Similarity	NPC471188
0.7557	Intermediate Similarity	NPC164014
0.7557	Intermediate Similarity	NPC75432
0.7557	Intermediate Similarity	NPC472693
0.7557	Intermediate Similarity	NPC246166
0.7557	Intermediate Similarity	NPC472694
0.7554	Intermediate Similarity	NPC475400
0.7542	Intermediate Similarity	NPC45613
0.7542	Intermediate Similarity	NPC188895
0.7541	Intermediate Similarity	NPC174099
0.7538	Intermediate Similarity	NPC223351
0.7538	Intermediate Similarity	NPC65627
0.7537	Intermediate Similarity	NPC147561
0.7536	Intermediate Similarity	NPC475549
0.7534	Intermediate Similarity	NPC144010
0.7521	Intermediate Similarity	NPC211439
0.7521	Intermediate Similarity	NPC146351

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 NPC144547 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	953
0.2-0.3	995
0.3-0.4	2563
0.4-0.5	2603
0.5-0.6	1300
0.6-0.7	389
0.7-0.8	45
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9397	High Similarity	NPD3412	Clinical (unspecified phase)
0.8621	High Similarity	NPD1609	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1876	Approved
0.7803	Intermediate Similarity	NPD7008	Discontinued
0.7795	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2182	Approved
0.7674	Intermediate Similarity	NPD3972	Approved
0.7672	Intermediate Similarity	NPD1238	Approved
0.7661	Intermediate Similarity	NPD5951	Approved
0.7638	Intermediate Similarity	NPD1651	Approved
0.7597	Intermediate Similarity	NPD1281	Approved
0.7563	Intermediate Similarity	NPD164	Approved
0.7554	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD3495	Discontinued
0.748	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD1929	Approved
0.7479	Intermediate Similarity	NPD1930	Approved
0.7479	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6287	Discontinued
0.7442	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1283	Approved
0.7405	Intermediate Similarity	NPD4878	Approved
0.7394	Intermediate Similarity	NPD7003	Approved
0.7372	Intermediate Similarity	NPD2979	Phase 3
0.7328	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2798	Approved
0.7305	Intermediate Similarity	NPD1471	Phase 3
0.7302	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD5909	Discontinued
0.7273	Intermediate Similarity	NPD1237	Approved
0.7265	Intermediate Similarity	NPD1989	Approved
0.725	Intermediate Similarity	NPD1932	Approved
0.7244	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3764	Approved
0.7226	Intermediate Similarity	NPD2313	Discontinued
0.7177	Intermediate Similarity	NPD2329	Discontinued
0.7174	Intermediate Similarity	NPD7713	Phase 3
0.7172	Intermediate Similarity	NPD7236	Approved
0.7163	Intermediate Similarity	NPD2799	Discontinued
0.7155	Intermediate Similarity	NPD7631	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.712	Intermediate Similarity	NPD2067	Discontinued
0.7114	Intermediate Similarity	NPD3226	Approved
0.7114	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2531	Phase 2
0.7113	Intermediate Similarity	NPD2438	Suspended
0.7105	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7094	Approved
0.7087	Intermediate Similarity	NPD6858	Approved
0.7083	Intermediate Similarity	NPD2066	Phase 3
0.7069	Intermediate Similarity	NPD7609	Phase 3
0.7063	Intermediate Similarity	NPD2344	Approved
0.7059	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3317	Approved
0.7047	Intermediate Similarity	NPD7239	Suspended
0.7042	Intermediate Similarity	NPD3748	Approved
0.704	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6039	Approved
0.7018	Intermediate Similarity	NPD650	Approved
0.7	Intermediate Similarity	NPD7458	Discontinued
0.7	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD2796	Approved
0.6992	Remote Similarity	NPD4879	Approved
0.6985	Remote Similarity	NPD1470	Approved
0.6985	Remote Similarity	NPD3266	Approved
0.6985	Remote Similarity	NPD3267	Approved
0.697	Remote Similarity	NPD5691	Approved
0.6966	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1202	Approved
0.694	Remote Similarity	NPD1201	Approved
0.6929	Remote Similarity	NPD8032	Phase 2
0.6918	Remote Similarity	NPD4628	Phase 3
0.6917	Remote Similarity	NPD2932	Approved
0.6917	Remote Similarity	NPD17	Approved
0.6911	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7009	Phase 2
0.6891	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2309	Approved
0.6871	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1508	Approved
0.6842	Remote Similarity	NPD3025	Approved
0.6842	Remote Similarity	NPD3024	Approved
0.6835	Remote Similarity	NPD7055	Discontinued
0.6835	Remote Similarity	NPD6832	Phase 2
0.6828	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7819	Suspended
0.6818	Remote Similarity	NPD7610	Discontinued
0.6812	Remote Similarity	NPD2788	Approved
0.6807	Remote Similarity	NPD1563	Approved
0.6806	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4308	Phase 3
0.6803	Remote Similarity	NPD3750	Approved
0.6791	Remote Similarity	NPD3019	Approved
0.6791	Remote Similarity	NPD5125	Phase 3
0.6791	Remote Similarity	NPD5126	Approved
0.6783	Remote Similarity	NPD1607	Approved
0.6767	Remote Similarity	NPD9545	Approved
0.6765	Remote Similarity	NPD1608	Approved
0.6742	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3023	Approved
0.6741	Remote Similarity	NPD3026	Approved
0.6739	Remote Similarity	NPD2797	Approved
0.6738	Remote Similarity	NPD3268	Approved
0.6718	Remote Similarity	NPD2629	Approved
0.6709	Remote Similarity	NPD5494	Approved
0.6694	Remote Similarity	NPD1843	Approved
0.6692	Remote Similarity	NPD6065	Approved
0.6691	Remote Similarity	NPD1611	Approved
0.669	Remote Similarity	NPD1510	Phase 2
0.669	Remote Similarity	NPD7961	Discontinued
0.6689	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD5978	Approved
0.6667	Remote Similarity	NPD5977	Approved
0.6645	Remote Similarity	NPD6279	Approved
0.6645	Remote Similarity	NPD6280	Approved
0.6645	Remote Similarity	NPD3869	Phase 3
0.6645	Remote Similarity	NPD3873	Phase 3
0.6645	Remote Similarity	NPD920	Approved
0.6644	Remote Similarity	NPD5404	Approved
0.6644	Remote Similarity	NPD5405	Approved
0.6644	Remote Similarity	NPD5406	Approved
0.6644	Remote Similarity	NPD5408	Approved
0.6644	Remote Similarity	NPD4476	Approved
0.6644	Remote Similarity	NPD2935	Discontinued
0.6644	Remote Similarity	NPD4477	Approved
0.6643	Remote Similarity	NPD3373	Approved
0.6643	Remote Similarity	NPD1240	Approved
0.6643	Remote Similarity	NPD3142	Approved
0.6643	Remote Similarity	NPD3140	Approved
0.6642	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1566	Phase 3
0.6639	Remote Similarity	NPD1239	Approved
0.6639	Remote Similarity	NPD1565	Approved
0.6639	Remote Similarity	NPD1564	Approved
0.6638	Remote Similarity	NPD9259	Approved
0.6638	Remote Similarity	NPD9257	Approved
0.6637	Remote Similarity	NPD942	Approved
0.6624	Remote Similarity	NPD7057	Phase 3
0.6624	Remote Similarity	NPD7058	Phase 2
0.6623	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2532	Approved
0.6623	Remote Similarity	NPD2533	Approved
0.6623	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2534	Approved
0.6622	Remote Similarity	NPD1243	Approved
0.6612	Remote Similarity	NPD1693	Approved
0.6605	Remote Similarity	NPD7473	Discontinued
0.66	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4618	Approved
0.6597	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4622	Approved
0.6594	Remote Similarity	NPD5327	Phase 3
0.6594	Remote Similarity	NPD5157	Phase 1
0.6594	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD5159	Phase 2
0.6593	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5585	Approved
0.6587	Remote Similarity	NPD3047	Approved
0.6587	Remote Similarity	NPD3048	Approved
0.6587	Remote Similarity	NPD3046	Approved
0.6581	Remote Similarity	NPD1087	Approved
0.6573	Remote Similarity	NPD6663	Approved
0.6571	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6085	Phase 2
0.6569	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2347	Approved
0.6564	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7177	Discontinued
0.6562	Remote Similarity	NPD6959	Discontinued
0.6561	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1549	Phase 2
0.6554	Remote Similarity	NPD2897	Discontinued
0.6547	Remote Similarity	NPD2198	Approved
0.6547	Remote Similarity	NPD2199	Approved
0.6547	Remote Similarity	NPD5667	Approved
0.6544	Remote Similarity	NPD2345	Approved
0.6543	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3887	Approved
0.6529	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5736	Approved
0.6524	Remote Similarity	NPD5844	Phase 1
0.6522	Remote Similarity	NPD6637	Approved
0.6522	Remote Similarity	NPD6232	Discontinued
0.6519	Remote Similarity	NPD1894	Discontinued
0.6519	Remote Similarity	NPD7741	Discontinued
0.6516	Remote Similarity	NPD6599	Discontinued
0.6516	Remote Similarity	NPD4380	Phase 2
0.6515	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6010	Discontinued
0.6513	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6647	Phase 2

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