NPASS Compound

Structure

NPC78047 OpenBabel07101719512D 27 31 0 0 1 0 0 0 0 0999 V2000 -5.8448 -1.1121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8448 -2.8442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1591 1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7634 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 -0.1045 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 -3.7570 -1.1691 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 0.6581 -2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3448 -1.9781 0.0000 C 0 0 0 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 1.4013 -0.8090 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 0.6581 -1.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5768 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3448 -1.9781 0.0000 C 0 0 2 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 -1.0739 -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 2 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 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1646 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 1.8271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7570 -2.7872 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 11 2 0 0 0 0 2 11 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 9 19 1 0 0 0 0 10 25 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 21 2 0 0 0 0 14 19 2 0 0 0 0 15 10 1 1 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 11 1 1 0 0 0 17 26 1 0 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 20 14 1 1 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.15
Volume:	371.782
LogP:	5.048
LogD:	3.652
LogS:	-6.155
# Rotatable Bonds:	3
TPSA:	46.15
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	3.897
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	3.299820309621282e-05
Pgp-inhibitor:	0.659
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	91.15377807617188%
Volume Distribution (VD):	0.837
Pgp-substrate:	8.403432846069336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.179
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.922
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.242
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.881

ADMET: Excretion

Clearance (CL):	9.545
Half-life (T1/2):	0.079

ADMET: Toxicity

hERG Blockers:	0.117
Human Hepatotoxicity (H-HT):	0.676
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.471
Rat Oral Acute Toxicity:	0.786
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.512
Carcinogencity:	0.339
Eye Corrosion:	0.003
Eye Irritation:	0.185
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC78047

Natural Product ID:	NPC78047
*Common Name:**	Epipervilline
IUPAC Name:	n.a.
Synonyms:	Epipervilline
Standard InCHIKey:	CLCLFKDEXVVDGI-WRWLIDTKSA-N
Standard InCHI:	InChI=1S/C22H22O5/c1-11(2)17-8-12-7-14-19(9-18(12)26-17)25-10-15-13-5-6-16(23-3)22(24-4)21(13)27-20(14)15/h5-7,9,15,17,20H,1,8,10H2,2-4H3/t15-,17-,20-/m1/s1
SMILES:	C=C(C)[C@H]1Cc2cc3c(cc2O1)OC[C@@H]1c2ccc(c(c2O[C@H]31)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224763
PubChem CID:	49866292
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO6364	Pongamiopsis pervilleana	Species	Fabaceae	Eukaryota	n.a.	Madagascar Dry Forest	n.a.	PMID[20804165]
NPO6364	Pongamiopsis pervilleana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	23200.0	nM	PMID[480096]

☑ 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 NPC78047 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	536
0.1-0.2	1588
0.2-0.3	4354
0.3-0.4	12691
0.4-0.5	5683
0.5-0.6	4309
0.6-0.7	7674
0.7-0.8	4499
0.8-0.85	888
0.85-0.9	418
0.9-0.95	55
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9542	High Similarity	NPC474478
0.938	High Similarity	NPC222127
0.938	High Similarity	NPC31707
0.938	High Similarity	NPC82862
0.9338	High Similarity	NPC472562
0.9338	High Similarity	NPC80326
0.9328	High Similarity	NPC477938
0.9302	High Similarity	NPC473092
0.9302	High Similarity	NPC473093
0.9302	High Similarity	NPC98745
0.9302	High Similarity	NPC8050
0.9275	High Similarity	NPC205316
0.9265	High Similarity	NPC58137
0.9265	High Similarity	NPC300798
0.9231	High Similarity	NPC54321
0.9231	High Similarity	NPC328682
0.9231	High Similarity	NPC281864
0.9225	High Similarity	NPC285725
0.9225	High Similarity	NPC50683
0.9225	High Similarity	NPC112571
0.9203	High Similarity	NPC280092
0.9203	High Similarity	NPC93323
0.9203	High Similarity	NPC12641
0.9203	High Similarity	NPC45257
0.9197	High Similarity	NPC174522
0.9191	High Similarity	NPC184797
0.9191	High Similarity	NPC27495
0.9191	High Similarity	NPC309124
0.9137	High Similarity	NPC469557
0.9137	High Similarity	NPC180953
0.913	High Similarity	NPC102044
0.913	High Similarity	NPC85264
0.913	High Similarity	NPC47633
0.9124	High Similarity	NPC263261
0.9124	High Similarity	NPC87725
0.9118	High Similarity	NPC236306
0.9118	High Similarity	NPC260741
0.9118	High Similarity	NPC473739
0.9118	High Similarity	NPC232164
0.9118	High Similarity	NPC70682
0.9104	High Similarity	NPC90083
0.9104	High Similarity	NPC170779
0.9098	High Similarity	NPC230219
0.9091	High Similarity	NPC470624
0.9091	High Similarity	NPC237169
0.9078	High Similarity	NPC71726
0.9077	High Similarity	NPC88297
0.9077	High Similarity	NPC186845
0.9077	High Similarity	NPC9891
0.907	High Similarity	NPC256015
0.907	High Similarity	NPC294156
0.907	High Similarity	NPC18449
0.907	High Similarity	NPC34902
0.907	High Similarity	NPC121783
0.9065	High Similarity	NPC63879
0.9058	High Similarity	NPC107161
0.9044	High Similarity	NPC474687
0.903	High Similarity	NPC263064
0.903	High Similarity	NPC26394
0.903	High Similarity	NPC266848
0.903	High Similarity	NPC136750
0.9007	High Similarity	NPC21776
0.9007	High Similarity	NPC16269
0.9	High Similarity	NPC181615
0.8986	High Similarity	NPC35216
0.8986	High Similarity	NPC247291
0.8978	High Similarity	NPC471388
0.8971	High Similarity	NPC3049
0.8971	High Similarity	NPC173660
0.8971	High Similarity	NPC248727
0.8971	High Similarity	NPC162659
0.8971	High Similarity	NPC265433
0.8971	High Similarity	NPC270456
0.8955	High Similarity	NPC261812
0.8955	High Similarity	NPC72046
0.8955	High Similarity	NPC65183
0.8955	High Similarity	NPC7744
0.8955	High Similarity	NPC475856
0.8944	High Similarity	NPC270751
0.8936	High Similarity	NPC324492
0.8936	High Similarity	NPC317053
0.8936	High Similarity	NPC260397
0.8929	High Similarity	NPC473108
0.8921	High Similarity	NPC475891
0.8921	High Similarity	NPC59841
0.8921	High Similarity	NPC204347
0.8921	High Similarity	NPC2613
0.8915	High Similarity	NPC261661
0.8913	High Similarity	NPC254759
0.8913	High Similarity	NPC160283
0.8913	High Similarity	NPC259519
0.8897	High Similarity	NPC470356
0.8897	High Similarity	NPC189474
0.8897	High Similarity	NPC94750
0.8897	High Similarity	NPC474206
0.8897	High Similarity	NPC61946
0.8897	High Similarity	NPC473413
0.8897	High Similarity	NPC126409
0.8897	High Similarity	NPC195022
0.8897	High Similarity	NPC224941
0.8897	High Similarity	NPC311430
0.8897	High Similarity	NPC121812
0.8897	High Similarity	NPC99572
0.8897	High Similarity	NPC112939
0.8897	High Similarity	NPC112246
0.8889	High Similarity	NPC85435
0.8881	High Similarity	NPC268917
0.8881	High Similarity	NPC280653
0.8881	High Similarity	NPC129784
0.8881	High Similarity	NPC236014
0.8881	High Similarity	NPC240521
0.8881	High Similarity	NPC228369
0.8881	High Similarity	NPC12875
0.8881	High Similarity	NPC476166
0.8881	High Similarity	NPC206224
0.8881	High Similarity	NPC300875
0.8881	High Similarity	NPC207892
0.8881	High Similarity	NPC17343
0.8881	High Similarity	NPC164574
0.8881	High Similarity	NPC196765
0.8881	High Similarity	NPC192255
0.8881	High Similarity	NPC150011
0.8881	High Similarity	NPC118114
0.8881	High Similarity	NPC129106
0.8873	High Similarity	NPC328567
0.8873	High Similarity	NPC320671
0.8873	High Similarity	NPC101376
0.8873	High Similarity	NPC327412
0.8873	High Similarity	NPC320970
0.8865	High Similarity	NPC178014
0.8865	High Similarity	NPC474749
0.8865	High Similarity	NPC42716
0.8865	High Similarity	NPC11422
0.8849	High Similarity	NPC471389
0.8849	High Similarity	NPC312199
0.8841	High Similarity	NPC25966
0.8841	High Similarity	NPC32630
0.8841	High Similarity	NPC127218
0.8841	High Similarity	NPC245207
0.8841	High Similarity	NPC319647
0.8841	High Similarity	NPC292882
0.8837	High Similarity	NPC172676
0.8837	High Similarity	NPC57268
0.8837	High Similarity	NPC216929
0.8837	High Similarity	NPC65933
0.8837	High Similarity	NPC312713
0.8837	High Similarity	NPC126935
0.8836	High Similarity	NPC159922
0.8832	High Similarity	NPC263367
0.8832	High Similarity	NPC177160
0.8832	High Similarity	NPC227503
0.8832	High Similarity	NPC470802
0.8832	High Similarity	NPC10737
0.8832	High Similarity	NPC16435
0.8832	High Similarity	NPC474639
0.8832	High Similarity	NPC209985
0.8832	High Similarity	NPC477939
0.8832	High Similarity	NPC156502
0.8832	High Similarity	NPC54743
0.8832	High Similarity	NPC230734
0.8832	High Similarity	NPC29799
0.8832	High Similarity	NPC306441
0.8824	High Similarity	NPC31530
0.8824	High Similarity	NPC49603
0.8824	High Similarity	NPC117048
0.8824	High Similarity	NPC16485
0.8824	High Similarity	NPC193026
0.8824	High Similarity	NPC124085
0.8824	High Similarity	NPC187616
0.8824	High Similarity	NPC317380
0.8815	High Similarity	NPC13005
0.8811	High Similarity	NPC301961
0.8811	High Similarity	NPC166584
0.8806	High Similarity	NPC470225
0.8806	High Similarity	NPC476399
0.8806	High Similarity	NPC27187
0.8803	High Similarity	NPC162193
0.8794	High Similarity	NPC114119
0.8794	High Similarity	NPC50250
0.8794	High Similarity	NPC471415
0.8794	High Similarity	NPC470097
0.8777	High Similarity	NPC216434
0.8777	High Similarity	NPC103448
0.8768	High Similarity	NPC211549
0.8768	High Similarity	NPC474282
0.8768	High Similarity	NPC107551
0.8768	High Similarity	NPC102904
0.8768	High Similarity	NPC326797
0.8768	High Similarity	NPC176051
0.8768	High Similarity	NPC276490
0.8768	High Similarity	NPC196420
0.8768	High Similarity	NPC103976
0.876	High Similarity	NPC472596
0.8759	High Similarity	NPC148893
0.8759	High Similarity	NPC25333
0.8759	High Similarity	NPC260898
0.8759	High Similarity	NPC165155
0.8759	High Similarity	NPC141765
0.8759	High Similarity	NPC151224
0.8759	High Similarity	NPC34103

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 NPC78047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	900
0.2-0.3	1781
0.3-0.4	2731
0.4-0.5	1645
0.5-0.6	915
0.6-0.7	593
0.7-0.8	145
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.854	High Similarity	NPD1612	Clinical (unspecified phase)
0.854	High Similarity	NPD1613	Approved
0.8394	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD3027	Phase 3
0.8309	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD5494	Approved
0.8248	Intermediate Similarity	NPD4908	Phase 1
0.814	Intermediate Similarity	NPD5283	Phase 1
0.8134	Intermediate Similarity	NPD1610	Phase 2
0.8043	Intermediate Similarity	NPD3018	Phase 2
0.8043	Intermediate Similarity	NPD2861	Phase 2
0.7987	Intermediate Similarity	NPD4967	Phase 2
0.7987	Intermediate Similarity	NPD4966	Approved
0.7987	Intermediate Similarity	NPD4965	Approved
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7929	Intermediate Similarity	NPD4625	Phase 3
0.7885	Intermediate Similarity	NPD6234	Discontinued
0.7883	Intermediate Similarity	NPD2983	Phase 2
0.7883	Intermediate Similarity	NPD2982	Phase 2
0.7868	Intermediate Similarity	NPD3705	Approved
0.7857	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6674	Discontinued
0.7792	Intermediate Similarity	NPD1934	Approved
0.7792	Intermediate Similarity	NPD37	Approved
0.7785	Intermediate Similarity	NPD7199	Phase 2
0.7754	Intermediate Similarity	NPD4749	Approved
0.7746	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD1548	Phase 1
0.7688	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7228	Approved
0.7651	Intermediate Similarity	NPD7466	Approved
0.7607	Intermediate Similarity	NPD5844	Phase 1
0.7571	Intermediate Similarity	NPD8651	Approved
0.7551	Intermediate Similarity	NPD5588	Approved
0.7533	Intermediate Similarity	NPD6331	Phase 2
0.7517	Intermediate Similarity	NPD4060	Phase 1
0.7516	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3539	Phase 1
0.75	Intermediate Similarity	NPD5327	Phase 3
0.7483	Intermediate Similarity	NPD4536	Approved
0.7483	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4538	Approved
0.747	Intermediate Similarity	NPD7240	Approved
0.7468	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7466	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD5124	Phase 1
0.745	Intermediate Similarity	NPD3540	Phase 1
0.7434	Intermediate Similarity	NPD7124	Phase 2
0.7434	Intermediate Similarity	NPD5058	Phase 3
0.7423	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6166	Phase 2
0.7421	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD3882	Suspended
0.7419	Intermediate Similarity	NPD1653	Approved
0.7405	Intermediate Similarity	NPD2801	Approved
0.7383	Intermediate Similarity	NPD2796	Approved
0.7379	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5976	Discontinued
0.7355	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3657	Discovery
0.7347	Intermediate Similarity	NPD5735	Approved
0.7346	Intermediate Similarity	NPD1247	Approved
0.7343	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.7329	Intermediate Similarity	NPD919	Approved
0.7315	Intermediate Similarity	NPD5960	Phase 3
0.7303	Intermediate Similarity	NPD3892	Phase 2
0.7301	Intermediate Similarity	NPD7229	Phase 3
0.7296	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7819	Suspended
0.7279	Intermediate Similarity	NPD3620	Phase 2
0.7279	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3926	Phase 2
0.7255	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6111	Discontinued
0.7246	Intermediate Similarity	NPD7074	Phase 3
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7241	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5177	Phase 3
0.7237	Intermediate Similarity	NPD1652	Phase 2
0.7234	Intermediate Similarity	NPD1091	Approved
0.7233	Intermediate Similarity	NPD3382	Approved
0.7233	Intermediate Similarity	NPD3384	Approved
0.7233	Intermediate Similarity	NPD3383	Approved
0.723	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD7157	Approved
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD1375	Discontinued
0.7219	Intermediate Similarity	NPD5763	Approved
0.7219	Intermediate Similarity	NPD7549	Discontinued
0.7218	Intermediate Similarity	NPD2684	Approved
0.7215	Intermediate Similarity	NPD4678	Approved
0.7215	Intermediate Similarity	NPD4380	Phase 2
0.7215	Intermediate Similarity	NPD4675	Approved
0.7212	Intermediate Similarity	NPD4481	Phase 3
0.7197	Intermediate Similarity	NPD4210	Discontinued
0.7195	Intermediate Similarity	NPD3051	Approved
0.7195	Intermediate Similarity	NPD6232	Discontinued
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4110	Phase 3
0.7186	Intermediate Similarity	NPD7054	Approved
0.7186	Intermediate Similarity	NPD8156	Discontinued
0.7179	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2424	Discontinued
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7161	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7212	Phase 2
0.7161	Intermediate Similarity	NPD1511	Approved
0.7161	Intermediate Similarity	NPD7213	Phase 3
0.716	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD7075	Discontinued
0.7152	Intermediate Similarity	NPD6100	Approved
0.7152	Intermediate Similarity	NPD2969	Approved
0.7152	Intermediate Similarity	NPD2970	Approved
0.7152	Intermediate Similarity	NPD6099	Approved
0.7152	Intermediate Similarity	NPD4005	Discontinued
0.7152	Intermediate Similarity	NPD2161	Phase 2
0.7143	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD5109	Approved
0.7143	Intermediate Similarity	NPD5111	Phase 2
0.7143	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD5110	Phase 2
0.7133	Intermediate Similarity	NPD2200	Suspended
0.7132	Intermediate Similarity	NPD7843	Approved
0.7132	Intermediate Similarity	NPD5535	Approved
0.7126	Intermediate Similarity	NPD8252	Approved
0.7126	Intermediate Similarity	NPD8099	Discontinued
0.7126	Intermediate Similarity	NPD8251	Approved
0.7124	Intermediate Similarity	NPD4237	Approved
0.7124	Intermediate Similarity	NPD4236	Phase 3
0.7115	Intermediate Similarity	NPD7447	Phase 1
0.7115	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1611	Approved
0.7105	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6004	Phase 3
0.7105	Intermediate Similarity	NPD6005	Phase 3
0.7105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6002	Phase 3
0.7101	Intermediate Similarity	NPD6671	Approved
0.7086	Intermediate Similarity	NPD3748	Approved
0.7083	Intermediate Similarity	NPD6696	Suspended
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1512	Approved
0.7067	Intermediate Similarity	NPD2157	Approved
0.7067	Intermediate Similarity	NPD6353	Approved
0.7059	Intermediate Similarity	NPD228	Approved
0.7059	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1549	Phase 2
0.7047	Intermediate Similarity	NPD4140	Approved
0.7044	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2438	Suspended
0.7037	Intermediate Similarity	NPD2563	Approved
0.7037	Intermediate Similarity	NPD2560	Approved
0.7032	Intermediate Similarity	NPD2677	Approved
0.703	Intermediate Similarity	NPD8127	Discontinued
0.703	Intermediate Similarity	NPD6959	Discontinued
0.7027	Intermediate Similarity	NPD6798	Discontinued
0.7021	Intermediate Similarity	NPD5585	Approved
0.7021	Intermediate Similarity	NPD1357	Approved
0.702	Intermediate Similarity	NPD7097	Phase 1
0.7019	Intermediate Similarity	NPD6801	Discontinued
0.7018	Intermediate Similarity	NPD7808	Phase 3
0.7015	Intermediate Similarity	NPD290	Approved
0.7007	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2489	Approved
0.7006	Intermediate Similarity	NPD27	Approved
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6994	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6788	Approved
0.6993	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD422	Phase 1
0.6988	Remote Similarity	NPD6071	Discontinued
0.698	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7313	Approved
0.6977	Remote Similarity	NPD7312	Approved
0.6977	Remote Similarity	NPD4577	Approved
0.6977	Remote Similarity	NPD7310	Approved
0.6977	Remote Similarity	NPD4578	Approved
0.6977	Remote Similarity	NPD7311	Approved
0.6975	Remote Similarity	NPD8455	Phase 2
0.6975	Remote Similarity	NPD1465	Phase 2
0.6974	Remote Similarity	NPD4108	Discontinued
0.6972	Remote Similarity	NPD5126	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