NPASS Compound

Structure

CID202594 OpenBabel06191715592D 25 27 0 0 0 0 0 0 0 0999 V2000 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 3.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 3.1340 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 -1.7321 3.0000 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 23 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 21 2 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.15
Volume:	354.303
LogP:	3.725
LogD:	3.174
LogS:	-3.783
# Rotatable Bonds:	3
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.86
Synthetic Accessibility Score:	3.341
Fsp3:	0.35
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:	-4.561
MDCK Permeability:	1.577462171553634e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.351

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	90.85210418701172%
Volume Distribution (VD):	1.26
Pgp-substrate:	9.00436782836914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.87
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.275
CYP2C19-substrate:	0.676
CYP2C9-inhibitor:	0.444
CYP2C9-substrate:	0.248
CYP2D6-inhibitor:	0.775
CYP2D6-substrate:	0.172
CYP3A4-inhibitor:	0.761
CYP3A4-substrate:	0.409

ADMET: Excretion

Clearance (CL):	8.534
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.949
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	0.279
Skin Sensitization:	0.199
Carcinogencity:	0.951
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.186

Download Data

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

Natural Product: NPC202594

Natural Product ID:	NPC202594
*Common Name:**	Cis-Avicennol
IUPAC Name:	6-[(Z)-3-hydroxy-3-methylbut-1-enyl]-5-methoxy-2,2-dimethylpyrano[2,3-h]chromen-8-one
Synonyms:	Cis-Avicennol
Standard InCHIKey:	AXYRILDCSATJFU-NTMALXAHSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-19(2,22)10-8-13-16(23-5)14-9-11-20(3,4)25-18(14)12-6-7-15(21)24-17(12)13/h6-11,22H,1-5H3/b10-8-
SMILES:	CC(C)(/C=Cc1c(c2C=CC(C)(C)Oc2c2ccc(=O)oc12)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465775
PubChem CID:	15118769
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO6026	Zanthoxylum chiloperone	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309303]
NPO8732	Thermopsis fabacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6026	Zanthoxylum chiloperone	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8732	Thermopsis fabacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11324	Philotheca citrina	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1806	Clibadium terebinthinaceum	Species	Asteraceae	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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	146000.0	nM	PMID[478449]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	200000.0	nM	PMID[478449]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	200000.0	nM	PMID[478449]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	200000.0	nM	PMID[478449]

☑ 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 NPC202594 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	360
0.1-0.2	1724
0.2-0.3	4652
0.3-0.4	10763
0.4-0.5	7484
0.5-0.6	4329
0.6-0.7	6017
0.7-0.8	4878
0.8-0.85	1545
0.85-0.9	704
0.9-0.95	228
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232692
0.9746	High Similarity	NPC150214
0.9664	High Similarity	NPC50720
0.95	High Similarity	NPC143725
0.936	High Similarity	NPC37009
0.936	High Similarity	NPC66430
0.935	High Similarity	NPC289316
0.9339	High Similarity	NPC154176
0.9339	High Similarity	NPC173350
0.9339	High Similarity	NPC290605
0.9268	High Similarity	NPC163248
0.9262	High Similarity	NPC291899
0.9213	High Similarity	NPC83535
0.9213	High Similarity	NPC141822
0.9213	High Similarity	NPC142563
0.9213	High Similarity	NPC1220
0.9213	High Similarity	NPC205797
0.9213	High Similarity	NPC291551
0.9213	High Similarity	NPC241165
0.918	High Similarity	NPC273772
0.918	High Similarity	NPC109675
0.912	High Similarity	NPC185066
0.912	High Similarity	NPC60704
0.912	High Similarity	NPC293642
0.912	High Similarity	NPC139595
0.9113	High Similarity	NPC471826
0.9106	High Similarity	NPC73413
0.9106	High Similarity	NPC201667
0.9106	High Similarity	NPC27671
0.9098	High Similarity	NPC257188
0.9098	High Similarity	NPC13007
0.904	High Similarity	NPC243688
0.9032	High Similarity	NPC471827
0.9032	High Similarity	NPC471828
0.9024	High Similarity	NPC472518
0.9016	High Similarity	NPC144418
0.8976	High Similarity	NPC32463
0.8968	High Similarity	NPC157212
0.8943	High Similarity	NPC248429
0.8943	High Similarity	NPC96286
0.8923	High Similarity	NPC472521
0.8915	High Similarity	NPC31849
0.8915	High Similarity	NPC469965
0.8889	High Similarity	NPC258567
0.8889	High Similarity	NPC121740
0.8889	High Similarity	NPC224774
0.888	High Similarity	NPC93219
0.888	High Similarity	NPC244495
0.8864	High Similarity	NPC47040
0.8864	High Similarity	NPC278600
0.8864	High Similarity	NPC35501
0.8864	High Similarity	NPC279573
0.8864	High Similarity	NPC211110
0.8864	High Similarity	NPC137262
0.8864	High Similarity	NPC37428
0.8864	High Similarity	NPC144512
0.8846	High Similarity	NPC131950
0.8846	High Similarity	NPC213173
0.8846	High Similarity	NPC147030
0.8846	High Similarity	NPC224475
0.8846	High Similarity	NPC180716
0.8837	High Similarity	NPC469956
0.8828	High Similarity	NPC113098
0.8819	High Similarity	NPC469453
0.8819	High Similarity	NPC472519
0.88	High Similarity	NPC111347
0.8797	High Similarity	NPC71903
0.878	High Similarity	NPC180006
0.878	High Similarity	NPC163200
0.878	High Similarity	NPC235190
0.8779	High Similarity	NPC472525
0.877	High Similarity	NPC298796
0.8769	High Similarity	NPC133956
0.8769	High Similarity	NPC296624
0.8769	High Similarity	NPC207002
0.8769	High Similarity	NPC469952
0.8769	High Similarity	NPC167111
0.8769	High Similarity	NPC318400
0.8769	High Similarity	NPC471910
0.8769	High Similarity	NPC469955
0.876	High Similarity	NPC272650
0.876	High Similarity	NPC267336
0.876	High Similarity	NPC29734
0.875	High Similarity	NPC168710
0.8731	High Similarity	NPC170812
0.8731	High Similarity	NPC195357
0.8731	High Similarity	NPC152771
0.8722	High Similarity	NPC151946
0.872	High Similarity	NPC315807
0.8712	High Similarity	NPC26954
0.8712	High Similarity	NPC38099
0.8702	High Similarity	NPC287182
0.8702	High Similarity	NPC267412
0.8702	High Similarity	NPC195343
0.8702	High Similarity	NPC47163
0.8702	High Similarity	NPC319859
0.8702	High Similarity	NPC326600
0.8702	High Similarity	NPC50896
0.8702	High Similarity	NPC18804
0.8702	High Similarity	NPC62366
0.8702	High Similarity	NPC198381
0.8702	High Similarity	NPC166672
0.8702	High Similarity	NPC84894
0.8702	High Similarity	NPC127888
0.8702	High Similarity	NPC260265
0.8702	High Similarity	NPC100986
0.8702	High Similarity	NPC74655
0.8702	High Similarity	NPC164269
0.8702	High Similarity	NPC204353
0.8692	High Similarity	NPC123954
0.8692	High Similarity	NPC14248
0.8692	High Similarity	NPC194277
0.8692	High Similarity	NPC19157
0.8689	High Similarity	NPC152306
0.8689	High Similarity	NPC265547
0.8682	High Similarity	NPC80170
0.8657	High Similarity	NPC312881
0.8647	High Similarity	NPC184861
0.8647	High Similarity	NPC153818
0.8647	High Similarity	NPC294456
0.8647	High Similarity	NPC232246
0.8647	High Similarity	NPC212124
0.8647	High Similarity	NPC225106
0.8647	High Similarity	NPC281014
0.8647	High Similarity	NPC155963
0.8636	High Similarity	NPC472424
0.8636	High Similarity	NPC86892
0.8636	High Similarity	NPC471909
0.8636	High Similarity	NPC61499
0.8636	High Similarity	NPC281241
0.8636	High Similarity	NPC471625
0.8629	High Similarity	NPC302107
0.8626	High Similarity	NPC163557
0.8626	High Similarity	NPC469449
0.8626	High Similarity	NPC7526
0.8626	High Similarity	NPC222036
0.8618	High Similarity	NPC281356
0.8607	High Similarity	NPC263754
0.8607	High Similarity	NPC183154
0.8605	High Similarity	NPC474289
0.8593	High Similarity	NPC310370
0.8593	High Similarity	NPC183642
0.8593	High Similarity	NPC287286
0.8583	High Similarity	NPC168259
0.8582	High Similarity	NPC38153
0.8571	High Similarity	NPC177281
0.8571	High Similarity	NPC476455
0.8571	High Similarity	NPC471630
0.8571	High Similarity	NPC188380
0.8571	High Similarity	NPC224543
0.8571	High Similarity	NPC55615
0.8571	High Similarity	NPC128529
0.8571	High Similarity	NPC78746
0.8571	High Similarity	NPC149320
0.8571	High Similarity	NPC160727
0.8571	High Similarity	NPC283019
0.8561	High Similarity	NPC253574
0.8561	High Similarity	NPC55149
0.8561	High Similarity	NPC307412
0.8561	High Similarity	NPC98179
0.856	High Similarity	NPC52247
0.856	High Similarity	NPC187868
0.8548	High Similarity	NPC247553
0.854	High Similarity	NPC471824
0.8537	High Similarity	NPC96705
0.8529	High Similarity	NPC221173
0.8527	High Similarity	NPC199204
0.8525	High Similarity	NPC128633
0.8516	High Similarity	NPC234109
0.8516	High Similarity	NPC188327
0.8496	Intermediate Similarity	NPC469675
0.8496	Intermediate Similarity	NPC33986
0.8485	Intermediate Similarity	NPC2363
0.8485	Intermediate Similarity	NPC54503
0.8485	Intermediate Similarity	NPC472522
0.8478	Intermediate Similarity	NPC469701
0.8478	Intermediate Similarity	NPC295696
0.8467	Intermediate Similarity	NPC470555
0.8456	Intermediate Similarity	NPC472343
0.8456	Intermediate Similarity	NPC279851
0.8456	Intermediate Similarity	NPC472520
0.8433	Intermediate Similarity	NPC167517
0.8433	Intermediate Similarity	NPC283331
0.8409	Intermediate Similarity	NPC281558
0.837	Intermediate Similarity	NPC131198
0.837	Intermediate Similarity	NPC471068
0.837	Intermediate Similarity	NPC471069
0.8359	Intermediate Similarity	NPC159132
0.8358	Intermediate Similarity	NPC229128
0.8346	Intermediate Similarity	NPC55147
0.8345	Intermediate Similarity	NPC101255
0.8345	Intermediate Similarity	NPC475719
0.8345	Intermediate Similarity	NPC43716
0.8345	Intermediate Similarity	NPC85624
0.8345	Intermediate Similarity	NPC71739
0.8333	Intermediate Similarity	NPC319378
0.8333	Intermediate Similarity	NPC236419
0.8333	Intermediate Similarity	NPC472517
0.8321	Intermediate Similarity	NPC134360
0.8321	Intermediate Similarity	NPC155552

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 NPC202594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	1003
0.2-0.3	1684
0.3-0.4	2638
0.4-0.5	1935
0.5-0.6	1075
0.6-0.7	344
0.7-0.8	108
0.8-0.85	32
0.85-0.9	12
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9213	High Similarity	NPD5124	Phase 1
0.9213	High Similarity	NPD5123	Clinical (unspecified phase)
0.856	High Similarity	NPD422	Phase 1
0.7939	Intermediate Similarity	NPD3225	Approved
0.7852	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1548	Phase 1
0.7801	Intermediate Similarity	NPD1652	Phase 2
0.7778	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6801	Discontinued
0.7746	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3750	Approved
0.7744	Intermediate Similarity	NPD2797	Approved
0.7721	Intermediate Similarity	NPD1296	Phase 2
0.7704	Intermediate Similarity	NPD4908	Phase 1
0.7703	Intermediate Similarity	NPD7411	Suspended
0.7676	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3748	Approved
0.7623	Intermediate Similarity	NPD9697	Approved
0.7619	Intermediate Similarity	NPD5535	Approved
0.7591	Intermediate Similarity	NPD3268	Approved
0.7576	Intermediate Similarity	NPD1610	Phase 2
0.7557	Intermediate Similarity	NPD4626	Approved
0.7518	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7483	Intermediate Similarity	NPD7819	Suspended
0.7483	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6799	Approved
0.7465	Intermediate Similarity	NPD2796	Approved
0.7463	Intermediate Similarity	NPD4749	Approved
0.7451	Intermediate Similarity	NPD7075	Discontinued
0.7432	Intermediate Similarity	NPD5403	Approved
0.7432	Intermediate Similarity	NPD920	Approved
0.7431	Intermediate Similarity	NPD1243	Approved
0.7419	Intermediate Similarity	NPD3134	Approved
0.7394	Intermediate Similarity	NPD4308	Phase 3
0.7394	Intermediate Similarity	NPD7033	Discontinued
0.7388	Intermediate Similarity	NPD9717	Approved
0.7368	Intermediate Similarity	NPD3496	Discontinued
0.7361	Intermediate Similarity	NPD1549	Phase 2
0.736	Intermediate Similarity	NPD1358	Approved
0.7353	Intermediate Similarity	NPD3266	Approved
0.7353	Intermediate Similarity	NPD3267	Approved
0.7351	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5691	Approved
0.7343	Intermediate Similarity	NPD1551	Phase 2
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2800	Approved
0.7305	Intermediate Similarity	NPD4340	Discontinued
0.7297	Intermediate Similarity	NPD2533	Approved
0.7297	Intermediate Similarity	NPD2534	Approved
0.7297	Intermediate Similarity	NPD5401	Approved
0.7297	Intermediate Similarity	NPD2532	Approved
0.7292	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6599	Discontinued
0.7279	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.7254	Intermediate Similarity	NPD6651	Approved
0.7241	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1240	Approved
0.7234	Intermediate Similarity	NPD4060	Phase 1
0.7234	Intermediate Similarity	NPD4307	Phase 2
0.7226	Intermediate Similarity	NPD1203	Approved
0.7222	Intermediate Similarity	NPD2935	Discontinued
0.7214	Intermediate Similarity	NPD2313	Discontinued
0.7194	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6832	Phase 2
0.7181	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4380	Phase 2
0.717	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD8651	Approved
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD1607	Approved
0.7122	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3749	Approved
0.7113	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1613	Approved
0.7105	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4288	Approved
0.7097	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3817	Phase 2
0.7097	Intermediate Similarity	NPD5402	Approved
0.7092	Intermediate Similarity	NPD6798	Discontinued
0.7068	Intermediate Similarity	NPD7644	Approved
0.7059	Intermediate Similarity	NPD1091	Approved
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7051	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6666	Approved
0.7047	Intermediate Similarity	NPD6667	Approved
0.7037	Intermediate Similarity	NPD1778	Approved
0.7031	Intermediate Similarity	NPD2684	Approved
0.7027	Intermediate Similarity	NPD4628	Phase 3
0.7007	Intermediate Similarity	NPD2424	Discontinued
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7213	Phase 3
0.7	Intermediate Similarity	NPD7212	Phase 2
0.6986	Remote Similarity	NPD6099	Approved
0.6986	Remote Similarity	NPD6100	Approved
0.6972	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7549	Discontinued
0.6966	Remote Similarity	NPD7097	Phase 1
0.6962	Remote Similarity	NPD919	Approved
0.696	Remote Similarity	NPD940	Approved
0.696	Remote Similarity	NPD846	Approved
0.6954	Remote Similarity	NPD7447	Phase 1
0.6947	Remote Similarity	NPD7843	Approved
0.6934	Remote Similarity	NPD1611	Approved
0.6933	Remote Similarity	NPD7286	Phase 2
0.6929	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1019	Discontinued
0.6923	Remote Similarity	NPD2801	Approved
0.6917	Remote Similarity	NPD6671	Approved
0.6908	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3027	Phase 3
0.6901	Remote Similarity	NPD7095	Approved
0.6894	Remote Similarity	NPD1241	Discontinued
0.6889	Remote Similarity	NPD1894	Discontinued
0.6889	Remote Similarity	NPD9545	Approved
0.6887	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1511	Approved
0.6883	Remote Similarity	NPD3226	Approved
0.6879	Remote Similarity	NPD2861	Phase 2
0.6879	Remote Similarity	NPD3018	Phase 2
0.6875	Remote Similarity	NPD4140	Approved
0.6861	Remote Similarity	NPD3847	Discontinued
0.6859	Remote Similarity	NPD1934	Approved
0.6853	Remote Similarity	NPD7985	Registered
0.6853	Remote Similarity	NPD411	Approved
0.6848	Remote Similarity	NPD5953	Discontinued
0.6832	Remote Similarity	NPD7229	Phase 3
0.6832	Remote Similarity	NPD6232	Discontinued
0.6829	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD447	Suspended
0.6828	Remote Similarity	NPD6355	Discontinued
0.6828	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1933	Approved
0.6824	Remote Similarity	NPD2346	Discontinued
0.6822	Remote Similarity	NPD290	Approved
0.6815	Remote Similarity	NPD1465	Phase 2
0.6807	Remote Similarity	NPD6559	Discontinued
0.6806	Remote Similarity	NPD6233	Phase 2
0.68	Remote Similarity	NPD7003	Approved
0.6797	Remote Similarity	NPD5049	Phase 3
0.6797	Remote Similarity	NPD1512	Approved
0.6797	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6971	Discontinued
0.6791	Remote Similarity	NPD7157	Approved
0.6786	Remote Similarity	NPD6696	Suspended
0.6774	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6959	Discontinued
0.6767	Remote Similarity	NPD1398	Phase 1
0.6763	Remote Similarity	NPD1608	Approved
0.6757	Remote Similarity	NPD4477	Approved
0.6757	Remote Similarity	NPD2862	Discontinued
0.6757	Remote Similarity	NPD4476	Approved
0.6753	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7340	Approved
0.6741	Remote Similarity	NPD9493	Approved
0.6736	Remote Similarity	NPD3764	Approved
0.6736	Remote Similarity	NPD1048	Approved
0.6733	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6502	Phase 2
0.673	Remote Similarity	NPD3882	Suspended
0.6728	Remote Similarity	NPD5711	Approved
0.6728	Remote Similarity	NPD5710	Approved
0.6714	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2982	Phase 2
0.6714	Remote Similarity	NPD2983	Phase 2
0.6712	Remote Similarity	NPD230	Phase 1
0.6711	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5763	Approved
0.6711	Remote Similarity	NPD5762	Approved
0.6708	Remote Similarity	NPD5494	Approved
0.6707	Remote Similarity	NPD7473	Discontinued
0.6692	Remote Similarity	NPD1138	Approved
0.6691	Remote Similarity	NPD1535	Discovery
0.669	Remote Similarity	NPD2798	Approved
0.669	Remote Similarity	NPD3690	Phase 2
0.669	Remote Similarity	NPD3691	Phase 2
0.6689	Remote Similarity	NPD7466	Approved
0.6667	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD2415	Discontinued
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7199	Phase 2
0.6646	Remote Similarity	NPD37	Approved
0.6644	Remote Similarity	NPD2203	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