NPASS Compound

Structure

NPC29734 OpenBabel07101719152D 25 26 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 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -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 -7.7942 1.5000 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 14 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 23 1 0 0 0 0 5 9 1 0 0 0 0 5 14 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 24 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 15 17 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 1 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	365.496
LogP:	3.159
LogD:	2.959
LogS:	-4.036
# Rotatable Bonds:	8
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	3.268
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.687
MDCK Permeability:	2.09948393603554e-05
Pgp-inhibitor:	0.671
Pgp-substrate:	0.443
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	97.1141586303711%
Volume Distribution (VD):	0.579
Pgp-substrate:	2.4503862857818604%

ADMET: Metabolism

CYP1A2-inhibitor:	0.805
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.622
CYP2C19-substrate:	0.274
CYP2C9-inhibitor:	0.483
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.398
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.519

ADMET: Excretion

Clearance (CL):	9.339
Half-life (T1/2):	0.29

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.317
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.637
Carcinogencity:	0.115
Eye Corrosion:	0.003
Eye Irritation:	0.095
Respiratory Toxicity:	0.08

Download Data

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

Natural Product: NPC29734

Natural Product ID:	NPC29734
*Common Name:**	7-[(E,6R)-6-Hydroxy-7-Methoxy-3,7-Dimethyloct-2-Enoxy]Chromen-2-One
IUPAC Name:	7-[(E,6R)-6-hydroxy-7-methoxy-3,7-dimethyloct-2-enoxy]chromen-2-one
Synonyms:
Standard InCHIKey:	HODOWBFKRLQCBH-GPZRYRNASA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-14(5-9-18(21)20(2,3)23-4)11-12-24-16-8-6-15-7-10-19(22)25-17(15)13-16/h6-8,10-11,13,18,21H,5,9,12H2,1-4H3/b14-11+/t18-/m1/s1
SMILES:	C/C(=CCOc1ccc2ccc(=O)oc2c1)/CC[C@H](C(C)(C)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2346910
PubChem CID:	15008366
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[558521]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	>	30000.0	nM	PMID[558521]
NPT22409	PROTEIN COMPLEX	Mitochondrial complex I (NADH dehydrogenase)	Homo sapiens	IC50	=	19300.0	nM	PMID[558521]

☑ 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 NPC29734 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	340
0.1-0.2	1421
0.2-0.3	3753
0.3-0.4	8555
0.4-0.5	10068
0.5-0.6	4098
0.6-0.7	6063
0.7-0.8	5139
0.8-0.85	2391
0.85-0.9	686
0.9-0.95	155
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC113098
0.984	High Similarity	NPC272650
0.984	High Similarity	NPC267336
0.9685	High Similarity	NPC469449
0.9538	High Similarity	NPC155963
0.9535	High Similarity	NPC472525
0.952	High Similarity	NPC224774
0.952	High Similarity	NPC121740
0.952	High Similarity	NPC258567
0.9466	High Similarity	NPC151946
0.9462	High Similarity	NPC38099
0.9462	High Similarity	NPC26954
0.9457	High Similarity	NPC180716
0.9457	High Similarity	NPC213173
0.9457	High Similarity	NPC62366
0.9457	High Similarity	NPC224475
0.9444	High Similarity	NPC469453
0.9394	High Similarity	NPC312881
0.9389	High Similarity	NPC471069
0.9389	High Similarity	NPC471068
0.9389	High Similarity	NPC153818
0.9389	High Similarity	NPC232246
0.9323	High Similarity	NPC195357
0.9323	High Similarity	NPC287286
0.9323	High Similarity	NPC152771
0.9318	High Similarity	NPC279573
0.9318	High Similarity	NPC471071
0.9318	High Similarity	NPC471072
0.9318	High Similarity	NPC471070
0.9313	High Similarity	NPC188380
0.9313	High Similarity	NPC224543
0.9313	High Similarity	NPC78746
0.9308	High Similarity	NPC204353
0.9308	High Similarity	NPC98179
0.9308	High Similarity	NPC50896
0.9308	High Similarity	NPC326600
0.9308	High Similarity	NPC253574
0.9242	High Similarity	NPC294456
0.9242	High Similarity	NPC212124
0.9242	High Similarity	NPC184861
0.9242	High Similarity	NPC225106
0.9242	High Similarity	NPC281014
0.9237	High Similarity	NPC33986
0.9231	High Similarity	NPC31849
0.9231	High Similarity	NPC2363
0.9179	High Similarity	NPC300611
0.9173	High Similarity	NPC211110
0.9154	High Similarity	NPC14248
0.9141	High Similarity	NPC185066
0.9113	High Similarity	NPC163200
0.9113	High Similarity	NPC180006
0.9113	High Similarity	NPC235190
0.9084	High Similarity	NPC207002
0.9084	High Similarity	NPC296624
0.9084	High Similarity	NPC318400
0.9084	High Similarity	NPC133956
0.9084	High Similarity	NPC222036
0.9084	High Similarity	NPC471910
0.9084	High Similarity	NPC7526
0.9084	High Similarity	NPC167111
0.9051	High Similarity	NPC85624
0.9051	High Similarity	NPC469701
0.9048	High Similarity	NPC109675
0.9048	High Similarity	NPC273772
0.9037	High Similarity	NPC215512
0.9037	High Similarity	NPC476442
0.9023	High Similarity	NPC103409
0.9015	High Similarity	NPC74655
0.9015	High Similarity	NPC267412
0.9015	High Similarity	NPC287182
0.9015	High Similarity	NPC195343
0.9015	High Similarity	NPC47163
0.9015	High Similarity	NPC319859
0.9015	High Similarity	NPC198381
0.9015	High Similarity	NPC164269
0.9015	High Similarity	NPC18804
0.9015	High Similarity	NPC307412
0.9015	High Similarity	NPC127888
0.9015	High Similarity	NPC55149
0.9015	High Similarity	NPC260265
0.9015	High Similarity	NPC84894
0.9015	High Similarity	NPC100986
0.9015	High Similarity	NPC166672
0.9008	High Similarity	NPC194277
0.8986	High Similarity	NPC205361
0.8978	High Similarity	NPC471824
0.8976	High Similarity	NPC73413
0.8976	High Similarity	NPC201667
0.8976	High Similarity	NPC27671
0.8955	High Similarity	NPC131198
0.8952	High Similarity	NPC281356
0.8952	High Similarity	NPC298796
0.8947	High Similarity	NPC471909
0.8947	High Similarity	NPC86892
0.8947	High Similarity	NPC281241
0.8947	High Similarity	NPC471625
0.8947	High Similarity	NPC469675
0.8947	High Similarity	NPC472424
0.8923	High Similarity	NPC168710
0.8921	High Similarity	NPC296377
0.8921	High Similarity	NPC87950
0.8921	High Similarity	NPC471764
0.8915	High Similarity	NPC243688
0.8905	High Similarity	NPC138212
0.8898	High Similarity	NPC472518
0.8889	High Similarity	NPC164148
0.8889	High Similarity	NPC43500
0.8881	High Similarity	NPC177281
0.8881	High Similarity	NPC471630
0.8881	High Similarity	NPC160727
0.8881	High Similarity	NPC283331
0.8881	High Similarity	NPC55615
0.8881	High Similarity	NPC283019
0.8881	High Similarity	NPC128529
0.8881	High Similarity	NPC149320
0.8881	High Similarity	NPC476455
0.8871	High Similarity	NPC265547
0.8871	High Similarity	NPC152306
0.8857	High Similarity	NPC169510
0.8855	High Similarity	NPC19242
0.8855	High Similarity	NPC80170
0.8846	High Similarity	NPC472519
0.8841	High Similarity	NPC471763
0.8819	High Similarity	NPC96286
0.8819	High Similarity	NPC248429
0.881	High Similarity	NPC302107
0.8797	High Similarity	NPC141822
0.8797	High Similarity	NPC1220
0.8797	High Similarity	NPC291551
0.8797	High Similarity	NPC241165
0.8797	High Similarity	NPC142563
0.8797	High Similarity	NPC163557
0.8797	High Similarity	NPC205797
0.8788	High Similarity	NPC250727
0.8779	High Similarity	NPC474289
0.8777	High Similarity	NPC226722
0.876	High Similarity	NPC471828
0.876	High Similarity	NPC93219
0.876	High Similarity	NPC471827
0.876	High Similarity	NPC232692
0.876	High Similarity	NPC244495
0.876	High Similarity	NPC202594
0.8759	High Similarity	NPC279851
0.8759	High Similarity	NPC472520
0.8759	High Similarity	NPC138149
0.875	High Similarity	NPC144512
0.875	High Similarity	NPC315807
0.875	High Similarity	NPC50720
0.875	High Similarity	NPC290605
0.875	High Similarity	NPC173350
0.875	High Similarity	NPC37428
0.875	High Similarity	NPC137262
0.875	High Similarity	NPC278600
0.875	High Similarity	NPC47040
0.875	High Similarity	NPC35501
0.875	High Similarity	NPC154176
0.874	High Similarity	NPC52247
0.874	High Similarity	NPC187868
0.874	High Similarity	NPC144418
0.8731	High Similarity	NPC92830
0.873	High Similarity	NPC247553
0.872	High Similarity	NPC96705
0.8712	High Similarity	NPC32463
0.8712	High Similarity	NPC474491
0.871	High Similarity	NPC128633
0.8702	High Similarity	NPC199204
0.8696	High Similarity	NPC93640
0.8696	High Similarity	NPC20631
0.8692	High Similarity	NPC234109
0.8692	High Similarity	NPC188327
0.8692	High Similarity	NPC471826
0.8682	High Similarity	NPC291899
0.8672	High Similarity	NPC257188
0.8672	High Similarity	NPC13007
0.8672	High Similarity	NPC150214
0.8657	High Similarity	NPC36437
0.8657	High Similarity	NPC469965
0.8657	High Similarity	NPC241341
0.8657	High Similarity	NPC233018
0.8652	High Similarity	NPC476347
0.8652	High Similarity	NPC15577
0.8643	High Similarity	NPC476450
0.8626	High Similarity	NPC473993
0.8615	High Similarity	NPC168259
0.8613	High Similarity	NPC13067
0.8601	High Similarity	NPC103116
0.8593	High Similarity	NPC131950
0.8592	High Similarity	NPC476348
0.8592	High Similarity	NPC96294
0.8592	High Similarity	NPC187398
0.8583	High Similarity	NPC193193
0.8582	High Similarity	NPC137669
0.8582	High Similarity	NPC5423
0.8582	High Similarity	NPC281558
0.8582	High Similarity	NPC469956
0.8561	High Similarity	NPC139595
0.8561	High Similarity	NPC157212
0.8561	High Similarity	NPC293642
0.8561	High Similarity	NPC219923
0.8561	High Similarity	NPC87224

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 NPC29734 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	862
0.2-0.3	1757
0.3-0.4	2565
0.4-0.5	1947
0.5-0.6	1134
0.6-0.7	409
0.7-0.8	117
0.8-0.85	51
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD5124	Phase 1
0.8797	High Similarity	NPD5123	Clinical (unspecified phase)
0.8759	High Similarity	NPD1652	Phase 2
0.874	High Similarity	NPD422	Phase 1
0.8296	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1653	Approved
0.8125	Intermediate Similarity	NPD6799	Approved
0.8054	Intermediate Similarity	NPD6801	Discontinued
0.803	Intermediate Similarity	NPD1091	Approved
0.8015	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1548	Phase 1
0.7984	Intermediate Similarity	NPD290	Approved
0.7984	Intermediate Similarity	NPD1358	Approved
0.7959	Intermediate Similarity	NPD5403	Approved
0.7945	Intermediate Similarity	NPD5401	Approved
0.792	Intermediate Similarity	NPD2684	Approved
0.7919	Intermediate Similarity	NPD6599	Discontinued
0.7917	Intermediate Similarity	NPD4628	Phase 3
0.7914	Intermediate Similarity	NPD1613	Approved
0.7914	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD6798	Discontinued
0.7899	Intermediate Similarity	NPD1296	Phase 2
0.7883	Intermediate Similarity	NPD4908	Phase 1
0.7852	Intermediate Similarity	NPD3225	Approved
0.7843	Intermediate Similarity	NPD7075	Discontinued
0.7826	Intermediate Similarity	NPD3027	Phase 3
0.7823	Intermediate Similarity	NPD9697	Approved
0.7817	Intermediate Similarity	NPD7033	Discontinued
0.7812	Intermediate Similarity	NPD7843	Approved
0.7794	Intermediate Similarity	NPD2797	Approved
0.7793	Intermediate Similarity	NPD3750	Approved
0.7778	Intermediate Similarity	NPD2424	Discontinued
0.777	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2796	Approved
0.7761	Intermediate Similarity	NPD1610	Phase 2
0.776	Intermediate Similarity	NPD3134	Approved
0.773	Intermediate Similarity	NPD6355	Discontinued
0.773	Intermediate Similarity	NPD4340	Discontinued
0.7727	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3748	Approved
0.7682	Intermediate Similarity	NPD4380	Phase 2
0.7674	Intermediate Similarity	NPD5535	Approved
0.7671	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4060	Phase 1
0.7655	Intermediate Similarity	NPD1549	Phase 2
0.7643	Intermediate Similarity	NPD3268	Approved
0.7639	Intermediate Similarity	NPD1551	Phase 2
0.7634	Intermediate Similarity	NPD7157	Approved
0.7632	Intermediate Similarity	NPD7411	Suspended
0.7626	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5402	Approved
0.7597	Intermediate Similarity	NPD3817	Phase 2
0.7591	Intermediate Similarity	NPD8651	Approved
0.7589	Intermediate Similarity	NPD6233	Phase 2
0.7586	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5763	Approved
0.7586	Intermediate Similarity	NPD5762	Approved
0.7574	Intermediate Similarity	NPD9717	Approved
0.7556	Intermediate Similarity	NPD3496	Discontinued
0.7554	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7819	Suspended
0.7518	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4749	Approved
0.7516	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD7097	Phase 1
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7481	Intermediate Similarity	NPD1778	Approved
0.7468	Intermediate Similarity	NPD1934	Approved
0.7467	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4062	Phase 3
0.7448	Intermediate Similarity	NPD1510	Phase 2
0.7448	Intermediate Similarity	NPD4308	Phase 3
0.7447	Intermediate Similarity	NPD7095	Approved
0.7436	Intermediate Similarity	NPD7768	Phase 2
0.7419	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD1203	Approved
0.741	Intermediate Similarity	NPD3266	Approved
0.741	Intermediate Similarity	NPD3267	Approved
0.7407	Intermediate Similarity	NPD5691	Approved
0.7403	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1048	Approved
0.7386	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD920	Approved
0.7365	Intermediate Similarity	NPD1243	Approved
0.7358	Intermediate Similarity	NPD7199	Phase 2
0.7353	Intermediate Similarity	NPD4626	Approved
0.7346	Intermediate Similarity	NPD3818	Discontinued
0.7333	Intermediate Similarity	NPD7549	Discontinued
0.7333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3882	Suspended
0.7324	Intermediate Similarity	NPD4625	Phase 3
0.731	Intermediate Similarity	NPD1607	Approved
0.7308	Intermediate Similarity	NPD2801	Approved
0.7305	Intermediate Similarity	NPD3018	Phase 2
0.7301	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4140	Approved
0.7292	Intermediate Similarity	NPD4307	Phase 2
0.7285	Intermediate Similarity	NPD7213	Phase 3
0.7285	Intermediate Similarity	NPD7212	Phase 2
0.7273	Intermediate Similarity	NPD6559	Discontinued
0.7261	Intermediate Similarity	NPD2415	Discontinued
0.726	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4536	Approved
0.726	Intermediate Similarity	NPD4538	Approved
0.7248	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD447	Suspended
0.7241	Intermediate Similarity	NPD230	Phase 1
0.7237	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1019	Discontinued
0.7234	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD919	Approved
0.723	Intermediate Similarity	NPD7266	Discontinued
0.723	Intermediate Similarity	NPD6004	Phase 3
0.723	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6005	Phase 3
0.723	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6002	Phase 3
0.7226	Intermediate Similarity	NPD5846	Approved
0.7226	Intermediate Similarity	NPD6516	Phase 2
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7219	Intermediate Similarity	NPD6666	Approved
0.7219	Intermediate Similarity	NPD5058	Phase 3
0.7219	Intermediate Similarity	NPD6667	Approved
0.7218	Intermediate Similarity	NPD1241	Discontinued
0.7212	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2799	Discontinued
0.7206	Intermediate Similarity	NPD9545	Approved
0.7206	Intermediate Similarity	NPD1894	Discontinued
0.7203	Intermediate Similarity	NPD3180	Approved
0.7203	Intermediate Similarity	NPD3179	Approved
0.7197	Intermediate Similarity	NPD8455	Phase 2
0.7195	Intermediate Similarity	NPD7054	Approved
0.7192	Intermediate Similarity	NPD6653	Approved
0.7183	Intermediate Similarity	NPD2861	Phase 2
0.7174	Intermediate Similarity	NPD3847	Discontinued
0.7171	Intermediate Similarity	NPD1511	Approved
0.717	Intermediate Similarity	NPD3749	Approved
0.7165	Intermediate Similarity	NPD940	Approved
0.7165	Intermediate Similarity	NPD846	Approved
0.7163	Intermediate Similarity	NPD987	Approved
0.7162	Intermediate Similarity	NPD2935	Discontinued
0.7162	Intermediate Similarity	NPD6032	Approved
0.716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD7074	Phase 3
0.7152	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7143	Intermediate Similarity	NPD3685	Discontinued
0.7134	Intermediate Similarity	NPD37	Approved
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3536	Discontinued
0.7124	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7447	Phase 1
0.7123	Intermediate Similarity	NPD1933	Approved
0.7123	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5647	Approved
0.7111	Intermediate Similarity	NPD6671	Approved
0.7108	Intermediate Similarity	NPD6797	Phase 2
0.7107	Intermediate Similarity	NPD4966	Approved
0.7107	Intermediate Similarity	NPD4965	Approved
0.7107	Intermediate Similarity	NPD4967	Phase 2
0.7095	Intermediate Similarity	NPD5960	Phase 3
0.7095	Intermediate Similarity	NPD5588	Approved
0.7089	Intermediate Similarity	NPD1465	Phase 2
0.7078	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1512	Approved
0.7078	Intermediate Similarity	NPD5049	Phase 3
0.7071	Intermediate Similarity	NPD2981	Phase 2
0.7071	Intermediate Similarity	NPD1608	Approved
0.7067	Intermediate Similarity	NPD4534	Discontinued
0.7066	Intermediate Similarity	NPD7251	Discontinued
0.7047	Intermediate Similarity	NPD2239	Approved
0.7047	Intermediate Similarity	NPD6099	Approved
0.7047	Intermediate Similarity	NPD2240	Approved
0.7047	Intermediate Similarity	NPD6100	Approved
0.7044	Intermediate Similarity	NPD4288	Approved
0.7042	Intermediate Similarity	NPD6362	Approved
0.7039	Intermediate Similarity	NPD3887	Approved
0.7039	Intermediate Similarity	NPD2354	Approved
0.7037	Intermediate Similarity	NPD8127	Discontinued
0.7034	Intermediate Similarity	NPD2313	Discontinued
0.7034	Intermediate Similarity	NPD411	Approved
0.7032	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD291	Approved
0.7025	Intermediate Similarity	NPD4433	Discontinued

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