NPASS Compound

Structure

NPC2363 OpenBabel07101719152D 24 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4282 0.1340 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 -1.7321 -2.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 2.5000 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 -0.5000 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 -6.0622 1.5000 0.0000 C 0 0 2 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 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 8 1 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 13 2 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 14 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 1 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.13
Volume:	354.62
LogP:	3.764
LogD:	3.698
LogS:	-4.609
# Rotatable Bonds:	7
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	3.257
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.726
MDCK Permeability:	2.124014645232819e-05
Pgp-inhibitor:	0.414
Pgp-substrate:	0.44
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	99.18245697021484%
Volume Distribution (VD):	0.423
Pgp-substrate:	1.421876311302185%

ADMET: Metabolism

CYP1A2-inhibitor:	0.809
CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.85
CYP2C19-substrate:	0.157
CYP2C9-inhibitor:	0.701
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.559
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.137
CYP3A4-substrate:	0.431

ADMET: Excretion

Clearance (CL):	9.686
Half-life (T1/2):	0.238

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.166
Drug-inuced Liver Injury (DILI):	0.349
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.626
Carcinogencity:	0.063
Eye Corrosion:	0.004
Eye Irritation:	0.422
Respiratory Toxicity:	0.721

Download Data

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

Natural Product: NPC2363

Natural Product ID:	NPC2363
*Common Name:**	7-[(E,6R)-7-Chloro-6-Hydroxy-3,7-Dimethyloct-2-Enoxy]Chromen-2-One
IUPAC Name:	7-[(E,6R)-7-chloro-6-hydroxy-3,7-dimethyloct-2-enoxy]chromen-2-one
Synonyms:
Standard InCHIKey:	LJKOFXGMGDOURN-JIIJFUIFSA-N
Standard InCHI:	InChI=1S/C19H23ClO4/c1-13(4-8-17(21)19(2,3)20)10-11-23-15-7-5-14-6-9-18(22)24-16(14)12-15/h5-7,9-10,12,17,21H,4,8,11H2,1-3H3/b13-10+/t17-/m1/s1
SMILES:	C/C(=CCOc1ccc2c(c1)oc(=O)cc2)/CC[C@H](C(Cl)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346912
PubChem CID:	71717738
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins 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
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18760601]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[21875114]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434131]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26247834]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30579794]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2
Others	1

Activity Type	# Activity
Others	1
PROTEIN COMPLEX	100

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	30.0	%	PMID[465855]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	11100.0	nM	PMID[465855]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	16700.0	nM	PMID[465855]

☑ 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 NPC2363 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	341
0.1-0.2	1594
0.2-0.3	4262
0.3-0.4	10536
0.4-0.5	8429
0.5-0.6	4415
0.6-0.7	6353
0.7-0.8	5238
0.8-0.85	1199
0.85-0.9	294
0.9-0.95	35
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.937	High Similarity	NPC224774
0.937	High Similarity	NPC258567
0.937	High Similarity	NPC121740
0.9302	High Similarity	NPC113098
0.9297	High Similarity	NPC469453
0.9231	High Similarity	NPC267336
0.9231	High Similarity	NPC29734
0.9231	High Similarity	NPC272650
0.9091	High Similarity	NPC31849
0.8968	High Similarity	NPC235190
0.8968	High Similarity	NPC163200
0.8968	High Similarity	NPC180006
0.8947	High Similarity	NPC469449
0.8906	High Similarity	NPC273772
0.8906	High Similarity	NPC109675
0.8889	High Similarity	NPC26954
0.8889	High Similarity	NPC38099
0.8881	High Similarity	NPC224475
0.8881	High Similarity	NPC180716
0.8881	High Similarity	NPC326600
0.8881	High Similarity	NPC50896
0.8881	High Similarity	NPC213173
0.8881	High Similarity	NPC62366
0.8881	High Similarity	NPC204353
0.8872	High Similarity	NPC194277
0.8855	High Similarity	NPC185066
0.8837	High Similarity	NPC73413
0.8837	High Similarity	NPC27671
0.8837	High Similarity	NPC201667
0.8824	High Similarity	NPC131198
0.8824	High Similarity	NPC155963
0.8815	High Similarity	NPC472525
0.881	High Similarity	NPC281356
0.881	High Similarity	NPC298796
0.8788	High Similarity	NPC168710
0.8779	High Similarity	NPC243688
0.876	High Similarity	NPC472518
0.8759	High Similarity	NPC151946
0.8759	High Similarity	NPC279573
0.873	High Similarity	NPC152306
0.873	High Similarity	NPC265547
0.8712	High Similarity	NPC472519
0.8696	High Similarity	NPC312881
0.8686	High Similarity	NPC232246
0.8686	High Similarity	NPC471069
0.8686	High Similarity	NPC153818
0.8686	High Similarity	NPC471068
0.8682	High Similarity	NPC248429
0.8682	High Similarity	NPC96286
0.8672	High Similarity	NPC302107
0.8667	High Similarity	NPC163557
0.8657	High Similarity	NPC250727
0.8647	High Similarity	NPC474289
0.8633	High Similarity	NPC152771
0.8633	High Similarity	NPC138149
0.8633	High Similarity	NPC195357
0.8633	High Similarity	NPC287286
0.8626	High Similarity	NPC471828
0.8626	High Similarity	NPC244495
0.8626	High Similarity	NPC471827
0.8626	High Similarity	NPC93219
0.8623	High Similarity	NPC471070
0.8623	High Similarity	NPC211110
0.8623	High Similarity	NPC471071
0.8623	High Similarity	NPC471072
0.8615	High Similarity	NPC315807
0.8613	High Similarity	NPC224543
0.8613	High Similarity	NPC78746
0.8613	High Similarity	NPC188380
0.8605	High Similarity	NPC187868
0.8605	High Similarity	NPC144418
0.8605	High Similarity	NPC52247
0.8603	High Similarity	NPC98179
0.8603	High Similarity	NPC253574
0.8594	High Similarity	NPC247553
0.8593	High Similarity	NPC14248
0.8583	High Similarity	NPC96705
0.8582	High Similarity	NPC80170
0.8582	High Similarity	NPC32463
0.8571	High Similarity	NPC93640
0.8571	High Similarity	NPC128633
0.8571	High Similarity	NPC20631
0.8571	High Similarity	NPC199204
0.8561	High Similarity	NPC188327
0.8561	High Similarity	NPC234109
0.8551	High Similarity	NPC281014
0.8551	High Similarity	NPC184861
0.8551	High Similarity	NPC225106
0.8551	High Similarity	NPC294456
0.8551	High Similarity	NPC212124
0.854	High Similarity	NPC33986
0.8529	High Similarity	NPC133956
0.8529	High Similarity	NPC141822
0.8529	High Similarity	NPC318400
0.8529	High Similarity	NPC241165
0.8529	High Similarity	NPC1220
0.8529	High Similarity	NPC142563
0.8529	High Similarity	NPC205797
0.8529	High Similarity	NPC291551
0.8529	High Similarity	NPC222036
0.8529	High Similarity	NPC296624
0.8529	High Similarity	NPC7526
0.8529	High Similarity	NPC207002
0.8529	High Similarity	NPC471910
0.8529	High Similarity	NPC167111
0.85	High Similarity	NPC300611
0.8489	Intermediate Similarity	NPC278600
0.8489	Intermediate Similarity	NPC43500
0.8489	Intermediate Similarity	NPC144512
0.8489	Intermediate Similarity	NPC37428
0.8489	Intermediate Similarity	NPC137262
0.8489	Intermediate Similarity	NPC47040
0.8489	Intermediate Similarity	NPC164148
0.8489	Intermediate Similarity	NPC35501
0.8485	Intermediate Similarity	NPC168259
0.8485	Intermediate Similarity	NPC202594
0.8485	Intermediate Similarity	NPC232692
0.8478	Intermediate Similarity	NPC103409
0.8473	Intermediate Similarity	NPC290605
0.8473	Intermediate Similarity	NPC173350
0.8473	Intermediate Similarity	NPC154176
0.8473	Intermediate Similarity	NPC50720
0.8467	Intermediate Similarity	NPC166672
0.8467	Intermediate Similarity	NPC307412
0.8467	Intermediate Similarity	NPC198381
0.8467	Intermediate Similarity	NPC195343
0.8467	Intermediate Similarity	NPC74655
0.8467	Intermediate Similarity	NPC164269
0.8467	Intermediate Similarity	NPC47163
0.8467	Intermediate Similarity	NPC84894
0.8467	Intermediate Similarity	NPC127888
0.8467	Intermediate Similarity	NPC100986
0.8467	Intermediate Similarity	NPC55149
0.8467	Intermediate Similarity	NPC287182
0.8467	Intermediate Similarity	NPC319859
0.8467	Intermediate Similarity	NPC18804
0.8467	Intermediate Similarity	NPC260265
0.8467	Intermediate Similarity	NPC267412
0.845	Intermediate Similarity	NPC193193
0.8444	Intermediate Similarity	NPC19242
0.8433	Intermediate Similarity	NPC219923
0.8421	Intermediate Similarity	NPC471826
0.8421	Intermediate Similarity	NPC101894
0.8409	Intermediate Similarity	NPC291899
0.8406	Intermediate Similarity	NPC61499
0.8406	Intermediate Similarity	NPC86892
0.8406	Intermediate Similarity	NPC469675
0.8406	Intermediate Similarity	NPC472424
0.8406	Intermediate Similarity	NPC471625
0.8406	Intermediate Similarity	NPC281241
0.8406	Intermediate Similarity	NPC471909
0.8397	Intermediate Similarity	NPC13007
0.8397	Intermediate Similarity	NPC150214
0.8397	Intermediate Similarity	NPC257188
0.8394	Intermediate Similarity	NPC469965
0.8392	Intermediate Similarity	NPC469701
0.8392	Intermediate Similarity	NPC85624
0.8385	Intermediate Similarity	NPC319378
0.838	Intermediate Similarity	NPC229916
0.838	Intermediate Similarity	NPC138212
0.8369	Intermediate Similarity	NPC155552
0.8369	Intermediate Similarity	NPC476442
0.8369	Intermediate Similarity	NPC215512
0.8345	Intermediate Similarity	NPC55615
0.8345	Intermediate Similarity	NPC283019
0.8345	Intermediate Similarity	NPC149320
0.8345	Intermediate Similarity	NPC471630
0.8345	Intermediate Similarity	NPC177281
0.8345	Intermediate Similarity	NPC283331
0.8345	Intermediate Similarity	NPC476455
0.8345	Intermediate Similarity	NPC128529
0.8345	Intermediate Similarity	NPC160727
0.8333	Intermediate Similarity	NPC205361
0.8333	Intermediate Similarity	NPC131950
0.8322	Intermediate Similarity	NPC471824
0.8321	Intermediate Similarity	NPC469956
0.8308	Intermediate Similarity	NPC31314
0.8296	Intermediate Similarity	NPC293642
0.8296	Intermediate Similarity	NPC139595
0.8296	Intermediate Similarity	NPC157212
0.8296	Intermediate Similarity	NPC60704
0.8286	Intermediate Similarity	NPC14697
0.8286	Intermediate Similarity	NPC306365
0.8276	Intermediate Similarity	NPC87950
0.8276	Intermediate Similarity	NPC471764
0.8276	Intermediate Similarity	NPC296377
0.8271	Intermediate Similarity	NPC111347
0.8264	Intermediate Similarity	NPC101255
0.8264	Intermediate Similarity	NPC43716
0.8264	Intermediate Similarity	NPC475719
0.8264	Intermediate Similarity	NPC226722
0.8261	Intermediate Similarity	NPC241341
0.8261	Intermediate Similarity	NPC469955
0.8261	Intermediate Similarity	NPC469952
0.8261	Intermediate Similarity	NPC36437
0.8261	Intermediate Similarity	NPC233018
0.8239	Intermediate Similarity	NPC183642
0.8239	Intermediate Similarity	NPC310370
0.8219	Intermediate Similarity	NPC169510
0.8201	Intermediate Similarity	NPC92830

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 NPC2363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	967
0.2-0.3	1665
0.3-0.4	2656
0.4-0.5	1967
0.5-0.6	1113
0.6-0.7	343
0.7-0.8	111
0.8-0.85	33
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD422	Phase 1
0.8529	High Similarity	NPD5124	Phase 1
0.8529	High Similarity	NPD5123	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1652	Phase 2
0.8175	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1548	Phase 1
0.78	Intermediate Similarity	NPD1653	Approved
0.7786	Intermediate Similarity	NPD1296	Phase 2
0.777	Intermediate Similarity	NPD4908	Phase 1
0.7737	Intermediate Similarity	NPD3225	Approved
0.7698	Intermediate Similarity	NPD9697	Approved
0.7687	Intermediate Similarity	NPD3750	Approved
0.7681	Intermediate Similarity	NPD2797	Approved
0.766	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD2796	Approved
0.7651	Intermediate Similarity	NPD6799	Approved
0.7647	Intermediate Similarity	NPD1610	Phase 2
0.7638	Intermediate Similarity	NPD3134	Approved
0.7597	Intermediate Similarity	NPD6801	Discontinued
0.7586	Intermediate Similarity	NPD7033	Discontinued
0.7586	Intermediate Similarity	NPD3748	Approved
0.7578	Intermediate Similarity	NPD1358	Approved
0.7557	Intermediate Similarity	NPD5535	Approved
0.7551	Intermediate Similarity	NPD1549	Phase 2
0.7548	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3268	Approved
0.7534	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD7411	Suspended
0.7518	Intermediate Similarity	NPD1091	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.7483	Intermediate Similarity	NPD5401	Approved
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6599	Discontinued
0.7464	Intermediate Similarity	NPD9717	Approved
0.745	Intermediate Similarity	NPD4628	Phase 3
0.745	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD3496	Discontinued
0.7442	Intermediate Similarity	NPD290	Approved
0.7436	Intermediate Similarity	NPD7819	Suspended
0.7431	Intermediate Similarity	NPD1613	Approved
0.7431	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6798	Discontinued
0.7405	Intermediate Similarity	NPD7075	Discontinued
0.7397	Intermediate Similarity	NPD4536	Approved
0.7397	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4538	Approved
0.7394	Intermediate Similarity	NPD6832	Phase 2
0.7385	Intermediate Similarity	NPD2684	Approved
0.7372	Intermediate Similarity	NPD1778	Approved
0.7372	Intermediate Similarity	NPD6516	Phase 2
0.7372	Intermediate Similarity	NPD5846	Approved
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1510	Phase 2
0.7343	Intermediate Similarity	NPD3027	Phase 3
0.7342	Intermediate Similarity	NPD7768	Phase 2
0.732	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1240	Approved
0.7308	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3266	Approved
0.7305	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD3267	Approved
0.7299	Intermediate Similarity	NPD5691	Approved
0.7296	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7843	Approved
0.7292	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4749	Approved
0.7279	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD920	Approved
0.7267	Intermediate Similarity	NPD1243	Approved
0.726	Intermediate Similarity	NPD4340	Discontinued
0.726	Intermediate Similarity	NPD6355	Discontinued
0.7255	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD4626	Approved
0.7244	Intermediate Similarity	NPD4380	Phase 2
0.7237	Intermediate Similarity	NPD5058	Phase 3
0.7237	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD5588	Approved
0.723	Intermediate Similarity	NPD5960	Phase 3
0.7212	Intermediate Similarity	NPD5844	Phase 1
0.7211	Intermediate Similarity	NPD1607	Approved
0.7203	Intermediate Similarity	NPD454	Approved
0.72	Intermediate Similarity	NPD4534	Discontinued
0.72	Intermediate Similarity	NPD2424	Discontinued
0.7197	Intermediate Similarity	NPD5451	Approved
0.7192	Intermediate Similarity	NPD4060	Phase 1
0.7192	Intermediate Similarity	NPD4140	Approved
0.719	Intermediate Similarity	NPD7212	Phase 2
0.719	Intermediate Similarity	NPD7213	Phase 3
0.7183	Intermediate Similarity	NPD987	Approved
0.7171	Intermediate Similarity	NPD3887	Approved
0.717	Intermediate Similarity	NPD3817	Phase 2
0.717	Intermediate Similarity	NPD5402	Approved
0.7153	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1578	Phase 2
0.7133	Intermediate Similarity	NPD6002	Phase 3
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5763	Approved
0.7133	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1019	Discontinued
0.7133	Intermediate Similarity	NPD6004	Phase 3
0.7133	Intermediate Similarity	NPD6005	Phase 3
0.7132	Intermediate Similarity	NPD7157	Approved
0.7124	Intermediate Similarity	NPD6667	Approved
0.7124	Intermediate Similarity	NPD6666	Approved
0.7123	Intermediate Similarity	NPD6233	Phase 2
0.7114	Intermediate Similarity	NPD2799	Discontinued
0.7113	Intermediate Similarity	NPD8651	Approved
0.7111	Intermediate Similarity	NPD1241	Discontinued
0.7107	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4625	Phase 3
0.7101	Intermediate Similarity	NPD9545	Approved
0.7101	Intermediate Similarity	NPD1894	Discontinued
0.7097	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5958	Discontinued
0.7083	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2861	Phase 2
0.7075	Intermediate Similarity	NPD4307	Phase 2
0.7071	Intermediate Similarity	NPD3847	Discontinued
0.7067	Intermediate Similarity	NPD2935	Discontinued
0.7063	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2354	Approved
0.7055	Intermediate Similarity	NPD1048	Approved
0.7054	Intermediate Similarity	NPD846	Approved
0.7054	Intermediate Similarity	NPD940	Approved
0.7047	Intermediate Similarity	NPD7097	Phase 1
0.7044	Intermediate Similarity	NPD1934	Approved
0.7042	Intermediate Similarity	NPD3685	Discontinued
0.7032	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7447	Phase 1
0.703	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4062	Phase 3
0.6975	Remote Similarity	NPD3749	Approved
0.6972	Remote Similarity	NPD1608	Approved
0.6966	Remote Similarity	NPD3018	Phase 2
0.6957	Remote Similarity	NPD4288	Approved
0.6951	Remote Similarity	NPD7199	Phase 2
0.6946	Remote Similarity	NPD3818	Discontinued
0.6944	Remote Similarity	NPD6362	Approved
0.6941	Remote Similarity	NPD7549	Discontinued
0.6939	Remote Similarity	NPD411	Approved
0.6939	Remote Similarity	NPD2313	Discontinued
0.6933	Remote Similarity	NPD919	Approved
0.6928	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2534	Approved
0.6923	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD4359	Approved
0.6923	Remote Similarity	NPD2532	Approved
0.6914	Remote Similarity	NPD3882	Suspended
0.6913	Remote Similarity	NPD447	Suspended
0.6913	Remote Similarity	NPD230	Phase 1
0.6912	Remote Similarity	NPD821	Approved
0.6908	Remote Similarity	NPD2353	Approved
0.6908	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3691	Phase 2
0.6897	Remote Similarity	NPD3690	Phase 2
0.6894	Remote Similarity	NPD2801	Approved
0.6884	Remote Similarity	NPD6671	Approved
0.6883	Remote Similarity	NPD3892	Phase 2
0.6883	Remote Similarity	NPD4535	Phase 3
0.6882	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD6273	Approved
0.6871	Remote Similarity	NPD7095	Approved
0.6871	Remote Similarity	NPD5163	Phase 2
0.6871	Remote Similarity	NPD6971	Discontinued
0.6859	Remote Similarity	NPD1511	Approved
0.6855	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6099	Approved
0.6842	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD4477	Approved
0.6842	Remote Similarity	NPD968	Approved
0.6842	Remote Similarity	NPD6032	Approved
0.6842	Remote Similarity	NPD4476	Approved
0.6835	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9493	Approved
0.6832	Remote Similarity	NPD37	Approved
0.6826	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6166	Phase 2
0.6826	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5953	Discontinued
0.6813	Remote Similarity	NPD4972	Discontinued
0.681	Remote Similarity	NPD4965	Approved
0.681	Remote Similarity	NPD4967	Phase 2
0.681	Remote Similarity	NPD4966	Approved
0.6809	Remote Similarity	NPD5585	Approved
0.6807	Remote Similarity	NPD7229	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