NPASS Compound

Structure

CID151946 OpenBabel06191715522D 27 28 0 0 1 0 0 0 0 0999 V2000 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 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 -0.8660 -1.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 -1.5000 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 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 3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 1 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 2.5981 -3.5000 0.0000 C 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 11 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 25 1 0 0 0 0 6 11 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 26 1 0 0 0 0 15 25 1 0 0 0 0 16 21 2 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 1 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	380.44
LogP:	1.527
LogD:	1.472
LogS:	-2.845
# Rotatable Bonds:	7
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	3.706
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.778
MDCK Permeability:	2.9239763534860685e-05
Pgp-inhibitor:	0.646
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131
Plasma Protein Binding (PPB):	76.40799713134766%
Volume Distribution (VD):	1.174
Pgp-substrate:	16.741636276245117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.167
CYP1A2-substrate:	0.836
CYP2C19-inhibitor:	0.304
CYP2C19-substrate:	0.627
CYP2C9-inhibitor:	0.478
CYP2C9-substrate:	0.765
CYP2D6-inhibitor:	0.345
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.354

ADMET: Excretion

Clearance (CL):	8.358
Half-life (T1/2):	0.66

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.497
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.256
Skin Sensitization:	0.113
Carcinogencity:	0.068
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC151946

Natural Product ID:	NPC151946
*Common Name:**	[(1R,2S)-1,3-Dihydroxy-1-(7-Methoxy-2-Oxochromen-6-Yl)-3-Methylbutan-2-Yl] (E)-2-Methylbut-2-Enoate
IUPAC Name:	[(1R,2S)-1,3-dihydroxy-1-(7-methoxy-2-oxochromen-6-yl)-3-methylbutan-2-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	GFMYIOGFYYHKLA-ZRKIHGRPSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-6-11(2)19(23)27-18(20(3,4)24)17(22)13-9-12-7-8-16(21)26-14(12)10-15(13)25-5/h6-10,17-18,22,24H,1-5H3/b11-6+/t17-,18+/m1/s1
SMILES:	C/C=C(C)/C(=O)O[C@@H]([C@@H](c1cc2ccc(=O)oc2cc1OC)O)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1878168
PubChem CID:	10022392
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
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17238120]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18405608]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[18661821]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21417376]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21627108]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[7700984]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3127	Aralia continentalis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22273	Angelica pubescens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3127	Aralia continentalis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22273	Angelica pubescens	Species	Apiaceae	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
Potency	3

Activity Type	# Activity
Individual Protein	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PMID[497373]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[497373]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	35481.3	nM	PMID[497373]

☑ 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 NPC151946 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	354
0.1-0.2	1445
0.2-0.3	3612
0.3-0.4	8087
0.4-0.5	10358
0.5-0.6	4133
0.6-0.7	5657
0.7-0.8	4944
0.8-0.85	2797
0.85-0.9	1056
0.9-0.95	205
0.95-1	49

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC155963
0.985	High Similarity	NPC195357
0.985	High Similarity	NPC152771
0.9847	High Similarity	NPC26954
0.9847	High Similarity	NPC38099
0.9774	High Similarity	NPC312881
0.9771	High Similarity	NPC472525
0.9701	High Similarity	NPC287286
0.9699	High Similarity	NPC279573
0.9699	High Similarity	NPC211110
0.9695	High Similarity	NPC62366
0.9695	High Similarity	NPC224475
0.9695	High Similarity	NPC180716
0.9695	High Similarity	NPC326600
0.9695	High Similarity	NPC213173
0.9695	High Similarity	NPC204353
0.9695	High Similarity	NPC50896
0.9624	High Similarity	NPC232246
0.9624	High Similarity	NPC294456
0.9624	High Similarity	NPC281014
0.9624	High Similarity	NPC212124
0.9624	High Similarity	NPC184861
0.9624	High Similarity	NPC153818
0.9624	High Similarity	NPC225106
0.9618	High Similarity	NPC31849
0.9549	High Similarity	NPC188380
0.9549	High Similarity	NPC224543
0.9549	High Similarity	NPC78746
0.9474	High Similarity	NPC33986
0.9466	High Similarity	NPC29734
0.942	High Similarity	NPC469701
0.9398	High Similarity	NPC267412
0.9398	High Similarity	NPC47163
0.9398	High Similarity	NPC98179
0.9398	High Similarity	NPC198381
0.9398	High Similarity	NPC195343
0.9398	High Similarity	NPC74655
0.9398	High Similarity	NPC319859
0.9398	High Similarity	NPC253574
0.9398	High Similarity	NPC84894
0.9398	High Similarity	NPC127888
0.9398	High Similarity	NPC164269
0.9398	High Similarity	NPC260265
0.9398	High Similarity	NPC166672
0.9398	High Similarity	NPC18804
0.9398	High Similarity	NPC55149
0.9398	High Similarity	NPC287182
0.9398	High Similarity	NPC100986
0.9398	High Similarity	NPC307412
0.9394	High Similarity	NPC194277
0.9389	High Similarity	NPC113098
0.9348	High Similarity	NPC471824
0.9328	High Similarity	NPC471625
0.9328	High Similarity	NPC281241
0.9328	High Similarity	NPC472424
0.9328	High Similarity	NPC86892
0.9328	High Similarity	NPC471909
0.9323	High Similarity	NPC318400
0.9323	High Similarity	NPC167111
0.9323	High Similarity	NPC471910
0.9323	High Similarity	NPC133956
0.9323	High Similarity	NPC222036
0.9323	High Similarity	NPC207002
0.9323	High Similarity	NPC7526
0.9323	High Similarity	NPC296624
0.9318	High Similarity	NPC267336
0.9318	High Similarity	NPC272650
0.9281	High Similarity	NPC85624
0.9259	High Similarity	NPC283019
0.9259	High Similarity	NPC476455
0.9259	High Similarity	NPC128529
0.9259	High Similarity	NPC177281
0.9259	High Similarity	NPC149320
0.9259	High Similarity	NPC160727
0.9259	High Similarity	NPC55615
0.9259	High Similarity	NPC471630
0.9248	High Similarity	NPC14248
0.9237	High Similarity	NPC185066
0.922	High Similarity	NPC169510
0.9209	High Similarity	NPC471763
0.9191	High Similarity	NPC471069
0.9191	High Similarity	NPC471068
0.9185	High Similarity	NPC469675
0.9179	High Similarity	NPC469449
0.9179	High Similarity	NPC163557
0.9167	High Similarity	NPC168710
0.916	High Similarity	NPC224774
0.916	High Similarity	NPC121740
0.916	High Similarity	NPC258567
0.9149	High Similarity	NPC87950
0.9149	High Similarity	NPC296377
0.9149	High Similarity	NPC471764
0.9124	High Similarity	NPC471071
0.9124	High Similarity	NPC471072
0.9124	High Similarity	NPC471070
0.9118	High Similarity	NPC283331
0.9098	High Similarity	NPC80170
0.9091	High Similarity	NPC103116
0.9091	High Similarity	NPC469453
0.9015	High Similarity	NPC473993
0.9015	High Similarity	NPC243688
0.8993	High Similarity	NPC472520
0.8993	High Similarity	NPC300611
0.8993	High Similarity	NPC279851
0.8947	High Similarity	NPC199204
0.8947	High Similarity	NPC472519
0.8944	High Similarity	NPC205361
0.8931	High Similarity	NPC73413
0.8931	High Similarity	NPC201667
0.8897	High Similarity	NPC1220
0.8897	High Similarity	NPC291551
0.8897	High Similarity	NPC241165
0.8897	High Similarity	NPC141822
0.8897	High Similarity	NPC469965
0.8897	High Similarity	NPC205797
0.8897	High Similarity	NPC142563
0.8865	High Similarity	NPC229916
0.8865	High Similarity	NPC119640
0.8865	High Similarity	NPC183646
0.8864	High Similarity	NPC93219
0.8864	High Similarity	NPC471828
0.8864	High Similarity	NPC471827
0.8864	High Similarity	NPC244495
0.8855	High Similarity	NPC472518
0.8855	High Similarity	NPC273772
0.8855	High Similarity	NPC109675
0.8849	High Similarity	NPC164148
0.8849	High Similarity	NPC43500
0.8849	High Similarity	NPC35501
0.8849	High Similarity	NPC278600
0.8849	High Similarity	NPC47040
0.8849	High Similarity	NPC144512
0.8849	High Similarity	NPC137262
0.8849	High Similarity	NPC37428
0.8832	High Similarity	NPC131950
0.8815	High Similarity	NPC32463
0.8803	High Similarity	NPC476457
0.8797	High Similarity	NPC234109
0.8797	High Similarity	NPC471826
0.8797	High Similarity	NPC188327
0.8794	High Similarity	NPC184053
0.8788	High Similarity	NPC27671
0.8779	High Similarity	NPC248429
0.8779	High Similarity	NPC96286
0.8777	High Similarity	NPC131198
0.8776	High Similarity	NPC256141
0.8759	High Similarity	NPC2363
0.875	High Similarity	NPC250727
0.875	High Similarity	NPC103799
0.875	High Similarity	NPC476347
0.8741	High Similarity	NPC295696
0.8741	High Similarity	NPC226722
0.8732	High Similarity	NPC138212
0.8723	High Similarity	NPC183642
0.8723	High Similarity	NPC138149
0.8723	High Similarity	NPC215512
0.8723	High Similarity	NPC310370
0.8723	High Similarity	NPC476442
0.8722	High Similarity	NPC232692
0.8722	High Similarity	NPC202594
0.8707	High Similarity	NPC470264
0.8705	High Similarity	NPC103409
0.869	High Similarity	NPC476348
0.869	High Similarity	NPC187398
0.8662	High Similarity	NPC20631
0.8662	High Similarity	NPC93640
0.8652	High Similarity	NPC71903
0.8647	High Similarity	NPC291899
0.8647	High Similarity	NPC111347
0.8639	High Similarity	NPC180351
0.8633	High Similarity	NPC61499
0.8633	High Similarity	NPC472521
0.8626	High Similarity	NPC163200
0.8626	High Similarity	NPC235190
0.8626	High Similarity	NPC180006
0.8623	High Similarity	NPC83535
0.8623	High Similarity	NPC92805
0.8621	High Similarity	NPC15577
0.8613	High Similarity	NPC37009
0.8613	High Similarity	NPC66430
0.8611	High Similarity	NPC108994
0.8611	High Similarity	NPC475719
0.8611	High Similarity	NPC101255
0.8611	High Similarity	NPC43716
0.8611	High Similarity	NPC71739
0.8611	High Similarity	NPC106126
0.8603	High Similarity	NPC474289
0.8601	High Similarity	NPC236419
0.8592	High Similarity	NPC170812
0.8592	High Similarity	NPC155552
0.8582	High Similarity	NPC270256
0.8582	High Similarity	NPC221046
0.8582	High Similarity	NPC13067
0.8571	High Similarity	NPC20829
0.8571	High Similarity	NPC50720
0.8571	High Similarity	NPC290605
0.8571	High Similarity	NPC262585
0.8571	High Similarity	NPC120426
0.8571	High Similarity	NPC294522
0.8571	High Similarity	NPC21184

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 NPC151946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	873
0.2-0.3	1805
0.3-0.4	2526
0.4-0.5	1930
0.5-0.6	1116
0.6-0.7	386
0.7-0.8	139
0.8-0.85	46
0.85-0.9	16
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8897	High Similarity	NPD5124	Phase 1
0.8897	High Similarity	NPD5123	Clinical (unspecified phase)
0.8592	High Similarity	NPD1652	Phase 2
0.8561	High Similarity	NPD422	Phase 1
0.8278	Intermediate Similarity	NPD6801	Discontinued
0.8255	Intermediate Similarity	NPD1653	Approved
0.8224	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7075	Discontinued
0.8146	Intermediate Similarity	NPD4380	Phase 2
0.8143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2424	Discontinued
0.8028	Intermediate Similarity	NPD1613	Approved
0.8028	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD4628	Phase 3
0.8014	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6799	Approved
0.795	Intermediate Similarity	NPD5844	Phase 1
0.7949	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD5403	Approved
0.7943	Intermediate Similarity	NPD3027	Phase 3
0.7933	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3750	Approved
0.7905	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD4060	Phase 1
0.7885	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1091	Approved
0.7872	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4908	Phase 1
0.7871	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7411	Suspended
0.7852	Intermediate Similarity	NPD1548	Phase 1
0.7838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD5402	Approved
0.7815	Intermediate Similarity	NPD5401	Approved
0.7808	Intermediate Similarity	NPD7033	Discontinued
0.7792	Intermediate Similarity	NPD6599	Discontinued
0.7786	Intermediate Similarity	NPD2797	Approved
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7762	Intermediate Similarity	NPD1296	Phase 2
0.7762	Intermediate Similarity	NPD6798	Discontinued
0.7756	Intermediate Similarity	NPD7819	Suspended
0.7755	Intermediate Similarity	NPD2796	Approved
0.7754	Intermediate Similarity	NPD1610	Phase 2
0.7746	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6355	Discontinued
0.7714	Intermediate Similarity	NPD8651	Approved
0.7714	Intermediate Similarity	NPD3225	Approved
0.7712	Intermediate Similarity	NPD920	Approved
0.7707	Intermediate Similarity	NPD3817	Phase 2
0.7703	Intermediate Similarity	NPD6004	Phase 3
0.7703	Intermediate Similarity	NPD6005	Phase 3
0.7703	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6002	Phase 3
0.7703	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6559	Discontinued
0.7692	Intermediate Similarity	NPD1934	Approved
0.7687	Intermediate Similarity	NPD3748	Approved
0.7681	Intermediate Similarity	NPD3496	Discontinued
0.7676	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1549	Phase 2
0.7639	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3268	Approved
0.7635	Intermediate Similarity	NPD1551	Phase 2
0.7635	Intermediate Similarity	NPD2935	Discontinued
0.7634	Intermediate Similarity	NPD2684	Approved
0.7619	Intermediate Similarity	NPD7097	Phase 1
0.7609	Intermediate Similarity	NPD4626	Approved
0.7603	Intermediate Similarity	NPD4340	Discontinued
0.76	Intermediate Similarity	NPD1243	Approved
0.7586	Intermediate Similarity	NPD6233	Phase 2
0.7584	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5763	Approved
0.7584	Intermediate Similarity	NPD5762	Approved
0.7584	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4625	Phase 3
0.7568	Intermediate Similarity	NPD1510	Phase 2
0.7568	Intermediate Similarity	NPD4308	Phase 3
0.7566	Intermediate Similarity	NPD6667	Approved
0.7566	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6666	Approved
0.7561	Intermediate Similarity	NPD3818	Discontinued
0.7557	Intermediate Similarity	NPD1358	Approved
0.7557	Intermediate Similarity	NPD290	Approved
0.7537	Intermediate Similarity	NPD7843	Approved
0.7536	Intermediate Similarity	NPD5691	Approved
0.7533	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD8455	Phase 2
0.7532	Intermediate Similarity	NPD2801	Approved
0.7532	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD4536	Approved
0.75	Intermediate Similarity	NPD4538	Approved
0.75	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2415	Discontinued
0.7484	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD37	Approved
0.7468	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD2533	Approved
0.7453	Intermediate Similarity	NPD919	Approved
0.7451	Intermediate Similarity	NPD5058	Phase 3
0.745	Intermediate Similarity	NPD2799	Discontinued
0.7448	Intermediate Similarity	NPD7095	Approved
0.7447	Intermediate Similarity	NPD9717	Approved
0.744	Intermediate Similarity	NPD7549	Discontinued
0.7439	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6166	Phase 2
0.7439	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4965	Approved
0.7438	Intermediate Similarity	NPD3882	Suspended
0.7438	Intermediate Similarity	NPD4966	Approved
0.7438	Intermediate Similarity	NPD4967	Phase 2
0.7432	Intermediate Similarity	NPD6653	Approved
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1240	Approved
0.741	Intermediate Similarity	NPD7054	Approved
0.7407	Intermediate Similarity	NPD5535	Approved
0.7405	Intermediate Similarity	NPD9697	Approved
0.7403	Intermediate Similarity	NPD1511	Approved
0.7397	Intermediate Similarity	NPD2313	Discontinued
0.7379	Intermediate Similarity	NPD6832	Phase 2
0.7365	Intermediate Similarity	NPD7074	Phase 3
0.7365	Intermediate Similarity	NPD7472	Approved
0.7365	Intermediate Similarity	NPD447	Suspended
0.7365	Intermediate Similarity	NPD230	Phase 1
0.7362	Intermediate Similarity	NPD7199	Phase 2
0.7361	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1778	Approved
0.7351	Intermediate Similarity	NPD7266	Discontinued
0.7348	Intermediate Similarity	NPD3134	Approved
0.7347	Intermediate Similarity	NPD4062	Phase 3
0.7346	Intermediate Similarity	NPD6234	Discontinued
0.7337	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5588	Approved
0.7333	Intermediate Similarity	NPD5960	Phase 3
0.7321	Intermediate Similarity	NPD6797	Phase 2
0.7317	Intermediate Similarity	NPD6232	Discontinued
0.7315	Intermediate Similarity	NPD1607	Approved
0.7312	Intermediate Similarity	NPD1465	Phase 2
0.731	Intermediate Similarity	NPD2861	Phase 2
0.7308	Intermediate Similarity	NPD1512	Approved
0.7301	Intermediate Similarity	NPD5494	Approved
0.7297	Intermediate Similarity	NPD4140	Approved
0.7297	Intermediate Similarity	NPD4307	Phase 2
0.7292	Intermediate Similarity	NPD3266	Approved
0.7292	Intermediate Similarity	NPD1203	Approved
0.7292	Intermediate Similarity	NPD3267	Approved
0.7285	Intermediate Similarity	NPD6032	Approved
0.7284	Intermediate Similarity	NPD3749	Approved
0.7279	Intermediate Similarity	NPD7985	Registered
0.7278	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7251	Discontinued
0.7273	Intermediate Similarity	NPD6190	Approved
0.7256	Intermediate Similarity	NPD8127	Discontinued
0.7255	Intermediate Similarity	NPD2800	Approved
0.725	Intermediate Similarity	NPD4433	Discontinued
0.7246	Intermediate Similarity	NPD6671	Approved
0.7244	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7808	Phase 3
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7215	Intermediate Similarity	NPD3686	Approved
0.7215	Intermediate Similarity	NPD3687	Approved
0.7212	Intermediate Similarity	NPD7229	Phase 3
0.7202	Intermediate Similarity	NPD7286	Phase 2
0.7197	Intermediate Similarity	NPD5049	Phase 3
0.7186	Intermediate Similarity	NPD7473	Discontinued
0.7179	Intermediate Similarity	NPD7213	Phase 3
0.7179	Intermediate Similarity	NPD7212	Phase 2
0.7172	Intermediate Similarity	NPD987	Approved
0.7171	Intermediate Similarity	NPD4476	Approved
0.7171	Intermediate Similarity	NPD4477	Approved
0.7171	Intermediate Similarity	NPD6099	Approved
0.7171	Intermediate Similarity	NPD6100	Approved
0.717	Intermediate Similarity	NPD3226	Approved
0.7169	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1048	Approved
0.716	Intermediate Similarity	NPD4288	Approved
0.7158	Intermediate Similarity	NPD7583	Approved
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6959	Discontinued
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7447	Phase 1
0.7133	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1611	Approved
0.7124	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1019	Discontinued
0.7123	Intermediate Similarity	NPD3691	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data