NPASS Compound

Structure

CID271944 OpenBabel06191716082D 49 53 0 0 1 0 0 0 0 0999 V2000 7.6499 -5.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4999 -3.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 -3.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7999 -3.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5500 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4000 -1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2499 -0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2499 -3.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7999 -2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8500 -3.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0999 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2499 -2.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -4.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6499 -4.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5500 -0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2499 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2499 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2499 -4.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 -3.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9499 -2.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -2.9444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8500 -1.4722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8500 1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9499 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0999 -2.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 -4.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -1.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8500 -0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -0.9815 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 -5.0999 -1.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0999 -4.9074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 2.4537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5500 -0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7999 -0.9815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0999 -3.9259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7000 -4.9074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 -0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 11 1 0 0 0 0 4 21 2 0 0 0 0 5 8 1 0 0 0 0 5 23 2 0 0 0 0 6 9 2 0 0 0 0 6 23 1 0 0 0 0 7 14 2 0 0 0 0 7 23 1 0 0 0 0 8 25 2 0 0 0 0 9 25 1 0 0 0 0 10 12 2 0 0 0 0 10 26 1 0 0 0 0 11 28 1 0 0 0 0 12 27 1 0 0 0 0 13 15 2 0 0 0 0 13 29 1 0 0 0 0 14 32 1 0 0 0 0 15 33 1 0 0 0 0 16 22 1 0 0 0 0 16 30 1 0 0 0 0 17 22 2 0 0 0 0 17 31 1 0 0 0 0 18 24 2 0 0 0 0 18 34 1 0 0 0 0 19 24 1 0 0 0 0 19 35 2 0 0 0 0 20 26 2 0 0 0 0 20 36 1 0 0 0 0 24 39 1 0 0 0 0 25 41 1 0 0 0 0 26 42 1 0 0 0 0 27 36 2 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 32 1 0 0 0 0 29 40 2 0 0 0 0 30 27 1 1 0 0 0 30 37 1 0 0 0 0 31 37 1 0 0 0 0 31 38 1 6 0 0 0 32 43 2 0 0 0 0 33 38 2 0 0 0 0 33 44 1 0 0 0 0 34 45 1 0 0 0 0 35 46 1 0 0 0 0 36 47 1 0 0 0 0 37 39 1 6 0 0 0 38 40 1 0 0 0 0 39 48 2 0 0 0 0 40 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	662.25
Volume:	691.906
LogP:	7.156
LogD:	3.354
LogS:	-2.322
# Rotatable Bonds:	9
TPSA:	175.75
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.054
Synthetic Accessibility Score:	4.421
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.782
MDCK Permeability:	8.007716132851783e-06
Pgp-inhibitor:	0.142
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.115
20% Bioavailability (F20%):	0.328
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	99.96925354003906%
Volume Distribution (VD):	0.528
Pgp-substrate:	0.9658491015434265%

ADMET: Metabolism

CYP1A2-inhibitor:	0.597
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.949
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.768
CYP2D6-substrate:	0.483
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	8.878
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.34
Drug-inuced Liver Injury (DILI):	0.755
AMES Toxicity:	0.549
Rat Oral Acute Toxicity:	0.397
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.967
Carcinogencity:	0.184
Eye Corrosion:	0.003
Eye Irritation:	0.881
Respiratory Toxicity:	0.207

Download Data

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

Natural Product: NPC271944

Natural Product ID:	NPC271944
*Common Name:**	Kuwanon R
IUPAC Name:	(E)-1-[3-[(1S,5S,6R)-6-[3,5-dihydroxy-4-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:	Kuwanon R
Standard InCHIKey:	PXFKYAIDSYKIJA-DLBCFTNOSA-N
Standard InCHI:	InChI=1S/C40H38O9/c1-21(2)4-11-28-34(45)18-24(19-35(28)46)39(48)37-30(27-12-10-26(42)20-36(27)47)16-22(3)17-31(37)38-33(44)15-13-29(40(38)49)32(43)14-7-23-5-8-25(41)9-6-23/h4-10,12-15,17-20,30-31,37,41-42,44-47,49H,11,16H2,1-3H3/b14-7+/t30-,31+,37-/m1/s1
SMILES:	CC(=CCc1c(cc(cc1O)C(=O)[C@@H]1[C@H](CC(=C[C@@H]1c1c(ccc(C(=O)/C=C/c2ccc(cc2)O)c1O)O)C)c1ccc(cc1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL570526
PubChem CID:	45485202
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO2578	Morus sp.	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19072214]
NPO2578	Morus sp.	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	5
Others	2

Activity Type	# Activity
CELL-LINE	1
Individual Protein	4
Others	1
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	IC50	=	3170.0	nM	PMID[468214]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	1640000.0	nM	PMID[468215]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Vmax	=	5.95	microM/min	PMID[468215]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	8200.0	nM	PMID[468215]
NPT20904	CELL-LINE	Hep 3B2	Homo sapiens	IC50	=	3510.0	nM	PMID[468214]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	6420.0	nM	PMID[468214]
NPT2	Others	Unspecified		IC50	=	3200.0	nM	PMID[468216]

☑ 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 NPC271944 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	420
0.1-0.2	1587
0.2-0.3	3608
0.3-0.4	9654
0.4-0.5	9732
0.5-0.6	5012
0.6-0.7	6522
0.7-0.8	5487
0.8-0.85	536
0.85-0.9	114
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC85393
1.0	High Similarity	NPC110882
0.9366	High Similarity	NPC293545
0.9366	High Similarity	NPC174905
0.9366	High Similarity	NPC451542
0.9366	High Similarity	NPC474203
0.9366	High Similarity	NPC313047
0.9366	High Similarity	NPC295712
0.9241	High Similarity	NPC37709
0.9167	High Similarity	NPC227841
0.9155	High Similarity	NPC169452
0.9155	High Similarity	NPC181560
0.9122	High Similarity	NPC35
0.9116	High Similarity	NPC477221
0.9097	High Similarity	NPC296752
0.9091	High Similarity	NPC246638
0.9085	High Similarity	NPC242994
0.9085	High Similarity	NPC138099
0.9078	High Similarity	NPC44960
0.9078	High Similarity	NPC474110
0.9034	High Similarity	NPC10764
0.9028	High Similarity	NPC19631
0.9028	High Similarity	NPC239136
0.9028	High Similarity	NPC193555
0.9014	High Similarity	NPC473622
0.9007	High Similarity	NPC191976
0.898	High Similarity	NPC290194
0.8966	High Similarity	NPC471682
0.8944	High Similarity	NPC471905
0.8944	High Similarity	NPC53206
0.8944	High Similarity	NPC53414
0.8897	High Similarity	NPC257644
0.8882	High Similarity	NPC54830
0.8882	High Similarity	NPC56049
0.8873	High Similarity	NPC254847
0.8865	High Similarity	NPC166480
0.8865	High Similarity	NPC282780
0.8857	High Similarity	NPC175738
0.8854	High Similarity	NPC253730
0.8854	High Similarity	NPC286230
0.8844	High Similarity	NPC12402
0.8844	High Similarity	NPC471683
0.8794	High Similarity	NPC267205
0.8792	High Similarity	NPC152233
0.8777	High Similarity	NPC109123
0.8767	High Similarity	NPC474961
0.8767	High Similarity	NPC135524
0.8766	High Similarity	NPC90497
0.875	High Similarity	NPC87723
0.875	High Similarity	NPC324447
0.8732	High Similarity	NPC44437
0.8732	High Similarity	NPC472262
0.8732	High Similarity	NPC287604
0.8732	High Similarity	NPC161964
0.8732	High Similarity	NPC475088
0.8726	High Similarity	NPC169471
0.8725	High Similarity	NPC475348
0.8725	High Similarity	NPC261271
0.871	High Similarity	NPC470342
0.871	High Similarity	NPC195136
0.871	High Similarity	NPC472060
0.871	High Similarity	NPC472052
0.8705	High Similarity	NPC473017
0.8699	High Similarity	NPC204045
0.8699	High Similarity	NPC305845
0.8693	High Similarity	NPC226656
0.8693	High Similarity	NPC37253
0.8693	High Similarity	NPC66508
0.8693	High Similarity	NPC79375
0.869	High Similarity	NPC143438
0.8684	High Similarity	NPC43345
0.8681	High Similarity	NPC53001
0.8671	High Similarity	NPC251336
0.8671	High Similarity	NPC283088
0.8649	High Similarity	NPC193703
0.8649	High Similarity	NPC21599
0.8645	High Similarity	NPC105584
0.8643	High Similarity	NPC474998
0.8633	High Similarity	NPC116513
0.8633	High Similarity	NPC72158
0.8633	High Similarity	NPC23126
0.8633	High Similarity	NPC266689
0.8633	High Similarity	NPC162612
0.8633	High Similarity	NPC105157
0.8633	High Similarity	NPC103356
0.8633	High Similarity	NPC100067
0.8633	High Similarity	NPC30501
0.8633	High Similarity	NPC169250
0.8633	High Similarity	NPC190043
0.8633	High Similarity	NPC98254
0.863	High Similarity	NPC225243
0.8621	High Similarity	NPC13715
0.8621	High Similarity	NPC20210
0.8618	High Similarity	NPC476551
0.8618	High Similarity	NPC476552
0.8618	High Similarity	NPC476553
0.8611	High Similarity	NPC118919
0.8591	High Similarity	NPC282957
0.8591	High Similarity	NPC471473
0.8591	High Similarity	NPC471523
0.8591	High Similarity	NPC34482
0.8591	High Similarity	NPC471524
0.8591	High Similarity	NPC194949
0.8582	High Similarity	NPC259942
0.8581	High Similarity	NPC208258
0.8571	High Similarity	NPC21305
0.8571	High Similarity	NPC221777
0.8562	High Similarity	NPC190457
0.8561	High Similarity	NPC62952
0.8561	High Similarity	NPC8745
0.8561	High Similarity	NPC267846
0.8553	High Similarity	NPC205766
0.8552	High Similarity	NPC62272
0.8542	High Similarity	NPC249272
0.8542	High Similarity	NPC290803
0.8533	High Similarity	NPC470570
0.8531	High Similarity	NPC225051
0.8528	High Similarity	NPC101991
0.8526	High Similarity	NPC324736
0.8526	High Similarity	NPC15815
0.8526	High Similarity	NPC326084
0.8523	High Similarity	NPC471906
0.8523	High Similarity	NPC48762
0.8523	High Similarity	NPC244691
0.8521	High Similarity	NPC474517
0.8521	High Similarity	NPC72669
0.8514	High Similarity	NPC73061
0.8514	High Similarity	NPC137649
0.8514	High Similarity	NPC469520
0.8511	High Similarity	NPC92624
0.8489	Intermediate Similarity	NPC10926
0.8483	Intermediate Similarity	NPC264112
0.8483	Intermediate Similarity	NPC65005
0.8483	Intermediate Similarity	NPC194764
0.8481	Intermediate Similarity	NPC473012
0.8472	Intermediate Similarity	NPC12070
0.8472	Intermediate Similarity	NPC50924
0.8472	Intermediate Similarity	NPC270899
0.8471	Intermediate Similarity	NPC475449
0.8471	Intermediate Similarity	NPC121647
0.8471	Intermediate Similarity	NPC226462
0.8471	Intermediate Similarity	NPC98023
0.8471	Intermediate Similarity	NPC476506
0.8471	Intermediate Similarity	NPC312993
0.8462	Intermediate Similarity	NPC1796
0.8462	Intermediate Similarity	NPC58685
0.8462	Intermediate Similarity	NPC257166
0.8462	Intermediate Similarity	NPC317580
0.8456	Intermediate Similarity	NPC297600
0.8452	Intermediate Similarity	NPC318270
0.8452	Intermediate Similarity	NPC66029
0.8446	Intermediate Similarity	NPC290550
0.8435	Intermediate Similarity	NPC162939
0.8428	Intermediate Similarity	NPC473009
0.8428	Intermediate Similarity	NPC159508
0.8425	Intermediate Similarity	NPC245923
0.8424	Intermediate Similarity	NPC121888
0.8418	Intermediate Similarity	NPC472261
0.8418	Intermediate Similarity	NPC301256
0.8418	Intermediate Similarity	NPC273467
0.8418	Intermediate Similarity	NPC312273
0.8418	Intermediate Similarity	NPC189552
0.8417	Intermediate Similarity	NPC13238
0.8414	Intermediate Similarity	NPC80035
0.8411	Intermediate Similarity	NPC314437
0.8411	Intermediate Similarity	NPC143685
0.8408	Intermediate Similarity	NPC18699
0.8408	Intermediate Similarity	NPC177650
0.8408	Intermediate Similarity	NPC51247
0.8408	Intermediate Similarity	NPC55443
0.8405	Intermediate Similarity	NPC24748
0.8405	Intermediate Similarity	NPC59491
0.8403	Intermediate Similarity	NPC37299
0.8403	Intermediate Similarity	NPC115458
0.8403	Intermediate Similarity	NPC213485
0.8403	Intermediate Similarity	NPC114183
0.8403	Intermediate Similarity	NPC40524
0.8403	Intermediate Similarity	NPC139074
0.8403	Intermediate Similarity	NPC180261
0.8392	Intermediate Similarity	NPC475042
0.8389	Intermediate Similarity	NPC26238
0.8389	Intermediate Similarity	NPC85310
0.8387	Intermediate Similarity	NPC470408
0.8387	Intermediate Similarity	NPC218870
0.8387	Intermediate Similarity	NPC182921
0.8387	Intermediate Similarity	NPC121568
0.8387	Intermediate Similarity	NPC474824
0.8385	Intermediate Similarity	NPC105414
0.8385	Intermediate Similarity	NPC324522
0.8385	Intermediate Similarity	NPC234497
0.8385	Intermediate Similarity	NPC472058
0.8385	Intermediate Similarity	NPC470341
0.838	Intermediate Similarity	NPC99731
0.8378	Intermediate Similarity	NPC203063
0.8378	Intermediate Similarity	NPC109232
0.8378	Intermediate Similarity	NPC275903
0.8375	Intermediate Similarity	NPC473010
0.8367	Intermediate Similarity	NPC4214
0.8366	Intermediate Similarity	NPC288840
0.8366	Intermediate Similarity	NPC291746

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 NPC271944 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	951
0.2-0.3	1454
0.3-0.4	2868
0.4-0.5	2138
0.5-0.6	962
0.6-0.7	296
0.7-0.8	93
0.8-0.85	8
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD7390	Discontinued
0.8873	High Similarity	NPD1509	Clinical (unspecified phase)
0.8552	High Similarity	NPD5405	Approved
0.8552	High Similarity	NPD5404	Approved
0.8552	High Similarity	NPD5406	Approved
0.8552	High Similarity	NPD5408	Approved
0.8217	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD943	Approved
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8105	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1470	Approved
0.8098	Intermediate Similarity	NPD7473	Discontinued
0.8037	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD1201	Approved
0.7937	Intermediate Similarity	NPD7768	Phase 2
0.7925	Intermediate Similarity	NPD7819	Suspended
0.7914	Intermediate Similarity	NPD6232	Discontinued
0.7852	Intermediate Similarity	NPD1607	Approved
0.7799	Intermediate Similarity	NPD7411	Suspended
0.7756	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1510	Phase 2
0.7736	Intermediate Similarity	NPD4380	Phase 2
0.7718	Intermediate Similarity	NPD1240	Approved
0.7632	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7075	Discontinued
0.7561	Intermediate Similarity	NPD3749	Approved
0.7543	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1549	Phase 2
0.7483	Intermediate Similarity	NPD1164	Approved
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7458	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7453	Intermediate Similarity	NPD3226	Approved
0.7453	Intermediate Similarity	NPD7458	Discontinued
0.7421	Intermediate Similarity	NPD2532	Approved
0.7421	Intermediate Similarity	NPD2534	Approved
0.7421	Intermediate Similarity	NPD2533	Approved
0.7419	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3750	Approved
0.7389	Intermediate Similarity	NPD7003	Approved
0.7378	Intermediate Similarity	NPD2801	Approved
0.7378	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5494	Approved
0.7358	Intermediate Similarity	NPD1511	Approved
0.7355	Intermediate Similarity	NPD2796	Approved
0.7325	Intermediate Similarity	NPD2800	Approved
0.7317	Intermediate Similarity	NPD1934	Approved
0.7296	Intermediate Similarity	NPD3300	Phase 2
0.729	Intermediate Similarity	NPD2799	Discontinued
0.729	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3882	Suspended
0.7289	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8166	Discontinued
0.7267	Intermediate Similarity	NPD1512	Approved
0.7267	Intermediate Similarity	NPD5844	Phase 1
0.7266	Intermediate Similarity	NPD4750	Phase 3
0.7246	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6099	Approved
0.7244	Intermediate Similarity	NPD6100	Approved
0.7241	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6559	Discontinued
0.7229	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7074	Phase 3
0.7215	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6801	Discontinued
0.7197	Intermediate Similarity	NPD2346	Discontinued
0.7197	Intermediate Similarity	NPD2344	Approved
0.7195	Intermediate Similarity	NPD6599	Discontinued
0.7192	Intermediate Similarity	NPD2932	Approved
0.7192	Intermediate Similarity	NPD3019	Approved
0.7168	Intermediate Similarity	NPD6020	Phase 2
0.7168	Intermediate Similarity	NPD7054	Approved
0.7158	Intermediate Similarity	NPD7699	Phase 2
0.7158	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD8151	Discontinued
0.7126	Intermediate Similarity	NPD7472	Approved
0.7124	Intermediate Similarity	NPD3764	Approved
0.7112	Intermediate Similarity	NPD7871	Phase 2
0.7112	Intermediate Similarity	NPD8320	Phase 1
0.7112	Intermediate Similarity	NPD7870	Phase 2
0.7112	Intermediate Similarity	NPD8319	Approved
0.711	Intermediate Similarity	NPD3818	Discontinued
0.7102	Intermediate Similarity	NPD7808	Phase 3
0.7088	Intermediate Similarity	NPD6535	Approved
0.7088	Intermediate Similarity	NPD6534	Approved
0.7086	Intermediate Similarity	NPD2798	Approved
0.707	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD7696	Phase 3
0.7059	Intermediate Similarity	NPD7697	Approved
0.7059	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD9269	Phase 2
0.7045	Intermediate Similarity	NPD7251	Discontinued
0.7037	Intermediate Similarity	NPD6799	Approved
0.703	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1551	Phase 2
0.7024	Intermediate Similarity	NPD3817	Phase 2
0.7019	Intermediate Similarity	NPD2309	Approved
0.7013	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD9268	Approved
0.6989	Remote Similarity	NPD6797	Phase 2
0.6989	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD6779	Approved
0.6989	Remote Similarity	NPD6776	Approved
0.6989	Remote Similarity	NPD5953	Discontinued
0.6989	Remote Similarity	NPD6782	Approved
0.6989	Remote Similarity	NPD6780	Approved
0.6989	Remote Similarity	NPD6777	Approved
0.6989	Remote Similarity	NPD6778	Approved
0.6968	Remote Similarity	NPD7435	Discontinued
0.6957	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3926	Phase 2
0.6923	Remote Similarity	NPD5402	Approved
0.6911	Remote Similarity	NPD7701	Phase 2
0.691	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2313	Discontinued
0.6894	Remote Similarity	NPD1243	Approved
0.6891	Remote Similarity	NPD7801	Approved
0.689	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD4908	Phase 1
0.6879	Remote Similarity	NPD5710	Approved
0.6879	Remote Similarity	NPD230	Phase 1
0.6879	Remote Similarity	NPD5711	Approved
0.6875	Remote Similarity	NPD7286	Phase 2
0.6864	Remote Similarity	NPD1465	Phase 2
0.6848	Remote Similarity	NPD6213	Phase 3
0.6848	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6212	Phase 3
0.6846	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7874	Approved
0.6831	Remote Similarity	NPD74	Approved
0.6831	Remote Similarity	NPD9266	Approved
0.6828	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6823	Phase 2
0.6821	Remote Similarity	NPD3972	Approved
0.6818	Remote Similarity	NPD7177	Discontinued
0.6816	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5403	Approved
0.6807	Remote Similarity	NPD920	Approved
0.6803	Remote Similarity	NPD9493	Approved
0.68	Remote Similarity	NPD3026	Approved
0.68	Remote Similarity	NPD3023	Approved
0.6796	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7229	Phase 3
0.6781	Remote Similarity	NPD5951	Approved
0.6779	Remote Similarity	NPD3025	Approved
0.6779	Remote Similarity	NPD3024	Approved
0.6763	Remote Similarity	NPD846	Approved
0.6763	Remote Similarity	NPD940	Approved
0.6761	Remote Similarity	NPD2342	Discontinued
0.6761	Remote Similarity	NPD9267	Approved
0.6761	Remote Similarity	NPD9264	Approved
0.6761	Remote Similarity	NPD9263	Approved
0.6761	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7635	Approved
0.6748	Remote Similarity	NPD4628	Phase 3
0.6731	Remote Similarity	NPD4625	Phase 3
0.6719	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7783	Phase 2
0.6711	Remote Similarity	NPD4878	Approved
0.6707	Remote Similarity	NPD6190	Approved
0.6706	Remote Similarity	NPD37	Approved
0.6691	Remote Similarity	NPD1242	Phase 1
0.6688	Remote Similarity	NPD3268	Approved
0.6688	Remote Similarity	NPD1203	Approved
0.6687	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5401	Approved
0.6685	Remote Similarity	NPD4287	Approved
0.6667	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD5029	Approved
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD5031	Approved
0.6667	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5027	Approved
0.6647	Remote Similarity	NPD6273	Approved
0.6646	Remote Similarity	NPD4308	Phase 3
0.6646	Remote Similarity	NPD6663	Approved
0.6634	Remote Similarity	NPD7654	Discontinued
0.6631	Remote Similarity	NPD4360	Phase 2
0.6631	Remote Similarity	NPD4363	Phase 3

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