NPASS Compound

Structure

NPC60704 OpenBabel07101718232D 28 31 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 -1.7321 0.0000 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 1.7321 -0.0000 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 0.8660 4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 2 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 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 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 0.0000 4.0000 0.0000 C 0 0 2 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 -0.8660 2.5000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 7 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 23 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 2 1 6 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 13 3 1 1 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 19 25 1 6 0 0 0 20 26 1 0 0 0 0 21 28 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	256.17
Volume:	272.032
LogP:	3.14
LogD:	1.977
LogS:	-2.875
# Rotatable Bonds:	6
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	4.278
Fsp3:	0.786
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:	-5.07
MDCK Permeability:	3.866834595100954e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.736

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	55.28216552734375%
Volume Distribution (VD):	0.256
Pgp-substrate:	38.18162536621094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.447
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.815
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	12.177
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.51
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.357
Maximum Recommended Daily Dose:	0.626
Skin Sensitization:	0.431
Carcinogencity:	0.862
Eye Corrosion:	0.485
Eye Irritation:	0.246
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC60704

Natural Product ID:	NPC60704
*Common Name:**	KEWWSURXGADRPV-VLXJIEOASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KEWWSURXGADRPV-VLXJIEOASA-N
Standard InCHI:	InChI=1S/C23H28O5/c1-7-8-14-11-16(24)27-22-17(14)21-15(9-10-23(4,5)28-21)20-18(22)19(25-6)12(2)13(3)26-20/h9-13,19H,7-8H2,1-6H3/t12-,13-,19-/m1/s1
SMILES:	CCCc1cc(=O)oc2c1c1c(C=CC(C)(C)O1)c1c2[C@@H]([C@H](C)[C@@H](C)O1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL329164
PubChem CID:	454256
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
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	Sarawak, Malaysia	n.a.	PMID[11430019]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1379639]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792623]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT315	Cell Line	CEM-SS	Homo sapiens	Max protection	=	35.0	%	PMID[528002]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	19000.0	nM	PMID[528002]

☑ 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 NPC60704 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	419
0.1-0.2	1575
0.2-0.3	3822
0.3-0.4	9019
0.4-0.5	9799
0.5-0.6	4209
0.6-0.7	6077
0.7-0.8	5384
0.8-0.85	1563
0.85-0.9	590
0.9-0.95	223
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC293642
1.0	High Similarity	NPC139595
0.9603	High Similarity	NPC469955
0.9603	High Similarity	NPC205797
0.9603	High Similarity	NPC141822
0.9603	High Similarity	NPC469952
0.9603	High Similarity	NPC291551
0.9603	High Similarity	NPC1220
0.9603	High Similarity	NPC241165
0.9603	High Similarity	NPC142563
0.9426	High Similarity	NPC50720
0.937	High Similarity	NPC469956
0.9344	High Similarity	NPC150214
0.9297	High Similarity	NPC469965
0.9268	High Similarity	NPC143725
0.9237	High Similarity	NPC144512
0.9237	High Similarity	NPC137262
0.9237	High Similarity	NPC35501
0.9237	High Similarity	NPC47040
0.9237	High Similarity	NPC37428
0.9237	High Similarity	NPC278600
0.9194	High Similarity	NPC291899
0.9154	High Similarity	NPC472424
0.9154	High Similarity	NPC86892
0.9154	High Similarity	NPC471625
0.9154	High Similarity	NPC471909
0.9154	High Similarity	NPC281241
0.9147	High Similarity	NPC207002
0.9147	High Similarity	NPC167111
0.9147	High Similarity	NPC133956
0.9147	High Similarity	NPC296624
0.9147	High Similarity	NPC318400
0.9147	High Similarity	NPC471910
0.9127	High Similarity	NPC289316
0.912	High Similarity	NPC202594
0.912	High Similarity	NPC232692
0.9084	High Similarity	NPC160727
0.9084	High Similarity	NPC471630
0.9084	High Similarity	NPC177281
0.9084	High Similarity	NPC283019
0.9084	High Similarity	NPC149320
0.9084	High Similarity	NPC55615
0.9084	High Similarity	NPC128529
0.9084	High Similarity	NPC476455
0.9077	High Similarity	NPC287182
0.9077	High Similarity	NPC84894
0.9077	High Similarity	NPC166672
0.9077	High Similarity	NPC195343
0.9077	High Similarity	NPC198381
0.9077	High Similarity	NPC319859
0.9077	High Similarity	NPC164269
0.9077	High Similarity	NPC127888
0.9077	High Similarity	NPC267412
0.9077	High Similarity	NPC18804
0.9077	High Similarity	NPC100986
0.9077	High Similarity	NPC74655
0.9077	High Similarity	NPC260265
0.9077	High Similarity	NPC47163
0.9048	High Similarity	NPC471826
0.9048	High Similarity	NPC163248
0.904	High Similarity	NPC201667
0.904	High Similarity	NPC27671
0.904	High Similarity	NPC73413
0.8968	High Similarity	NPC471827
0.8968	High Similarity	NPC471828
0.8963	High Similarity	NPC201820
0.896	High Similarity	NPC154176
0.896	High Similarity	NPC273772
0.896	High Similarity	NPC290605
0.896	High Similarity	NPC173350
0.896	High Similarity	NPC109675
0.896	High Similarity	NPC472518
0.8923	High Similarity	NPC14248
0.8915	High Similarity	NPC80170
0.8906	High Similarity	NPC472519
0.8889	High Similarity	NPC111347
0.888	High Similarity	NPC257188
0.888	High Similarity	NPC248429
0.888	High Similarity	NPC96286
0.888	High Similarity	NPC13007
0.8855	High Similarity	NPC222036
0.8855	High Similarity	NPC7526
0.8837	High Similarity	NPC168710
0.8815	High Similarity	NPC287286
0.881	High Similarity	NPC315807
0.8806	High Similarity	NPC279573
0.8806	High Similarity	NPC211110
0.8788	High Similarity	NPC131950
0.8788	High Similarity	NPC55149
0.8788	High Similarity	NPC307412
0.8779	High Similarity	NPC19157
0.876	High Similarity	NPC157212
0.876	High Similarity	NPC185066
0.876	High Similarity	NPC199204
0.875	High Similarity	NPC188327
0.875	High Similarity	NPC234109
0.8741	High Similarity	NPC312881
0.8731	High Similarity	NPC306365
0.8731	High Similarity	NPC232246
0.8731	High Similarity	NPC153818
0.8722	High Similarity	NPC469675
0.872	High Similarity	NPC180006
0.872	High Similarity	NPC235190
0.872	High Similarity	NPC163200
0.8712	High Similarity	NPC31849
0.8702	High Similarity	NPC37009
0.8702	High Similarity	NPC66430
0.8696	High Similarity	NPC469701
0.8676	High Similarity	NPC195357
0.8676	High Similarity	NPC152771
0.8657	High Similarity	NPC224543
0.8657	High Similarity	NPC78746
0.8657	High Similarity	NPC283331
0.8657	High Similarity	NPC188380
0.8651	High Similarity	NPC144418
0.8647	High Similarity	NPC184677
0.8647	High Similarity	NPC180716
0.8647	High Similarity	NPC62366
0.8647	High Similarity	NPC224475
0.8647	High Similarity	NPC213173
0.8643	High Similarity	NPC218300
0.8643	High Similarity	NPC282335
0.8629	High Similarity	NPC96705
0.8626	High Similarity	NPC113098
0.8626	High Similarity	NPC32463
0.8603	High Similarity	NPC71903
0.8593	High Similarity	NPC281014
0.8593	High Similarity	NPC184861
0.8593	High Similarity	NPC225106
0.8593	High Similarity	NPC155963
0.8593	High Similarity	NPC294456
0.8593	High Similarity	NPC212124
0.8593	High Similarity	NPC14697
0.8582	High Similarity	NPC472525
0.8571	High Similarity	NPC83535
0.8561	High Similarity	NPC29734
0.8561	High Similarity	NPC106126
0.8561	High Similarity	NPC108994
0.8561	High Similarity	NPC101255
0.8561	High Similarity	NPC267336
0.8561	High Similarity	NPC43716
0.8561	High Similarity	NPC272650
0.8561	High Similarity	NPC475719
0.856	High Similarity	NPC281356
0.856	High Similarity	NPC298796
0.8551	High Similarity	NPC183646
0.8551	High Similarity	NPC119640
0.854	High Similarity	NPC138149
0.854	High Similarity	NPC170812
0.8538	High Similarity	NPC121740
0.8538	High Similarity	NPC224774
0.8538	High Similarity	NPC258567
0.8538	High Similarity	NPC243688
0.8529	High Similarity	NPC38153
0.8529	High Similarity	NPC151946
0.8519	High Similarity	NPC26954
0.8519	High Similarity	NPC38099
0.8507	High Similarity	NPC253574
0.8507	High Similarity	NPC147030
0.8507	High Similarity	NPC98179
0.8507	High Similarity	NPC326600
0.8507	High Similarity	NPC50896
0.8507	High Similarity	NPC204353
0.8496	Intermediate Similarity	NPC194277
0.8496	Intermediate Similarity	NPC123954
0.8489	Intermediate Similarity	NPC476457
0.848	Intermediate Similarity	NPC265547
0.848	Intermediate Similarity	NPC152306
0.8478	Intermediate Similarity	NPC93640
0.8478	Intermediate Similarity	NPC20631
0.8473	Intermediate Similarity	NPC469453
0.8462	Intermediate Similarity	NPC101894
0.8456	Intermediate Similarity	NPC131198
0.8444	Intermediate Similarity	NPC33986
0.844	Intermediate Similarity	NPC471764
0.844	Intermediate Similarity	NPC87950
0.8433	Intermediate Similarity	NPC54503
0.8433	Intermediate Similarity	NPC472522
0.8433	Intermediate Similarity	NPC55147
0.8433	Intermediate Similarity	NPC163557
0.8433	Intermediate Similarity	NPC469449
0.8429	Intermediate Similarity	NPC85624
0.8413	Intermediate Similarity	NPC172253
0.8413	Intermediate Similarity	NPC59561
0.8406	Intermediate Similarity	NPC472523
0.8397	Intermediate Similarity	NPC149796
0.8394	Intermediate Similarity	NPC270256
0.8394	Intermediate Similarity	NPC307883
0.8385	Intermediate Similarity	NPC93219
0.8385	Intermediate Similarity	NPC244495
0.8358	Intermediate Similarity	NPC175159
0.8357	Intermediate Similarity	NPC471824
0.8321	Intermediate Similarity	NPC471068
0.8321	Intermediate Similarity	NPC471069
0.832	Intermediate Similarity	NPC128633
0.831	Intermediate Similarity	NPC296377
0.8309	Intermediate Similarity	NPC229128
0.8298	Intermediate Similarity	NPC295696
0.8296	Intermediate Similarity	NPC2363
0.8296	Intermediate Similarity	NPC77196

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 NPC60704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	955
0.2-0.3	1647
0.3-0.4	2601
0.4-0.5	1942
0.5-0.6	1107
0.6-0.7	371
0.7-0.8	125
0.8-0.85	26
0.85-0.9	17
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9603	High Similarity	NPD5123	Clinical (unspecified phase)
0.9603	High Similarity	NPD5124	Phase 1
0.8217	Intermediate Similarity	NPD422	Phase 1
0.8074	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1652	Phase 2
0.7926	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD4908	Phase 1
0.781	Intermediate Similarity	NPD1296	Phase 2
0.781	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3748	Approved
0.7717	Intermediate Similarity	NPD5535	Approved
0.7676	Intermediate Similarity	NPD2796	Approved
0.7669	Intermediate Similarity	NPD1610	Phase 2
0.7667	Intermediate Similarity	NPD7411	Suspended
0.7651	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1548	Phase 1
0.763	Intermediate Similarity	NPD3225	Approved
0.7586	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5691	Approved
0.7574	Intermediate Similarity	NPD3267	Approved
0.7574	Intermediate Similarity	NPD2797	Approved
0.7574	Intermediate Similarity	NPD3266	Approved
0.7566	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD3134	Approved
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7466	Intermediate Similarity	NPD3750	Approved
0.7451	Intermediate Similarity	NPD7819	Suspended
0.744	Intermediate Similarity	NPD9697	Approved
0.7429	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3268	Approved
0.7426	Intermediate Similarity	NPD4749	Approved
0.7419	Intermediate Similarity	NPD7075	Discontinued
0.7413	Intermediate Similarity	NPD7097	Phase 1
0.7403	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5403	Approved
0.74	Intermediate Similarity	NPD920	Approved
0.7397	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1243	Approved
0.7383	Intermediate Similarity	NPD5401	Approved
0.7383	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7033	Discontinued
0.7357	Intermediate Similarity	NPD4625	Phase 3
0.7355	Intermediate Similarity	NPD7768	Phase 2
0.7351	Intermediate Similarity	NPD1653	Approved
0.7329	Intermediate Similarity	NPD1549	Phase 2
0.7323	Intermediate Similarity	NPD1358	Approved
0.7315	Intermediate Similarity	NPD6799	Approved
0.7293	Intermediate Similarity	NPD7644	Approved
0.7286	Intermediate Similarity	NPD6832	Phase 2
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4626	Approved
0.7255	Intermediate Similarity	NPD4380	Phase 2
0.723	Intermediate Similarity	NPD7466	Approved
0.7226	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5844	Phase 1
0.7219	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5494	Approved
0.7211	Intermediate Similarity	NPD2424	Discontinued
0.7206	Intermediate Similarity	NPD3496	Discontinued
0.7203	Intermediate Similarity	NPD4307	Phase 2
0.7203	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4060	Phase 1
0.7203	Intermediate Similarity	NPD1613	Approved
0.72	Intermediate Similarity	NPD7213	Phase 3
0.72	Intermediate Similarity	NPD7212	Phase 2
0.7183	Intermediate Similarity	NPD6798	Discontinued
0.7153	Intermediate Similarity	NPD4340	Discontinued
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7134	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD8651	Approved
0.7095	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2861	Phase 2
0.7089	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4140	Approved
0.707	Intermediate Similarity	NPD3817	Phase 2
0.707	Intermediate Similarity	NPD5402	Approved
0.7055	Intermediate Similarity	NPD2200	Suspended
0.7048	Intermediate Similarity	NPD7549	Discontinued
0.7047	Intermediate Similarity	NPD6674	Discontinued
0.7044	Intermediate Similarity	NPD919	Approved
0.7042	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7447	Phase 1
0.7039	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7029	Intermediate Similarity	NPD1091	Approved
0.7029	Intermediate Similarity	NPD1611	Approved
0.702	Intermediate Similarity	NPD6667	Approved
0.702	Intermediate Similarity	NPD6666	Approved
0.7012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2799	Discontinued
0.7007	Intermediate Similarity	NPD1510	Phase 2
0.7007	Intermediate Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD2684	Approved
0.6992	Remote Similarity	NPD1241	Discontinued
0.6986	Remote Similarity	NPD6651	Approved
0.6981	Remote Similarity	NPD3749	Approved
0.6972	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6099	Approved
0.6959	Remote Similarity	NPD6100	Approved
0.6959	Remote Similarity	NPD1551	Phase 2
0.6944	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2313	Discontinued
0.6944	Remote Similarity	NPD7985	Registered
0.6943	Remote Similarity	NPD1934	Approved
0.6933	Remote Similarity	NPD2800	Approved
0.6933	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7843	Approved
0.6914	Remote Similarity	NPD7229	Phase 3
0.6913	Remote Similarity	NPD5762	Approved
0.6913	Remote Similarity	NPD5763	Approved
0.6906	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1019	Discontinued
0.6899	Remote Similarity	NPD8455	Phase 2
0.6897	Remote Similarity	NPD6233	Phase 2
0.6887	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4628	Phase 3
0.6884	Remote Similarity	NPD17	Approved
0.6884	Remote Similarity	NPD1778	Approved
0.6883	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5890	Approved
0.6879	Remote Similarity	NPD5889	Approved
0.6875	Remote Similarity	NPD3027	Phase 3
0.6861	Remote Similarity	NPD1894	Discontinued
0.6857	Remote Similarity	NPD9717	Approved
0.6855	Remote Similarity	NPD4288	Approved
0.6852	Remote Similarity	NPD6959	Discontinued
0.6849	Remote Similarity	NPD1240	Approved
0.6846	Remote Similarity	NPD2935	Discontinued
0.6842	Remote Similarity	NPD1139	Approved
0.6842	Remote Similarity	NPD1137	Approved
0.6829	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4536	Approved
0.6824	Remote Similarity	NPD4538	Approved
0.6824	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6585	Discontinued
0.6812	Remote Similarity	NPD5585	Approved
0.6809	Remote Similarity	NPD5327	Phase 3
0.6803	Remote Similarity	NPD4618	Approved
0.6803	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4622	Approved
0.6803	Remote Similarity	NPD1933	Approved
0.6797	Remote Similarity	NPD5058	Phase 3
0.6794	Remote Similarity	NPD290	Approved
0.6791	Remote Similarity	NPD1138	Approved
0.6786	Remote Similarity	NPD6559	Discontinued
0.6781	Remote Similarity	NPD8032	Phase 2
0.6776	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6273	Approved
0.6765	Remote Similarity	NPD6387	Discontinued
0.6765	Remote Similarity	NPD7157	Approved
0.6765	Remote Similarity	NPD6671	Approved
0.6759	Remote Similarity	NPD7095	Approved
0.6757	Remote Similarity	NPD1607	Approved
0.675	Remote Similarity	NPD2415	Discontinued
0.6748	Remote Similarity	NPD7199	Phase 2
0.6738	Remote Similarity	NPD1608	Approved
0.6736	Remote Similarity	NPD3018	Phase 2
0.6736	Remote Similarity	NPD2237	Approved
0.6735	Remote Similarity	NPD2979	Phase 3
0.6735	Remote Similarity	NPD2203	Discontinued
0.6733	Remote Similarity	NPD2438	Suspended
0.6733	Remote Similarity	NPD4476	Approved
0.6733	Remote Similarity	NPD4477	Approved
0.6731	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.673	Remote Similarity	NPD37	Approved
0.6727	Remote Similarity	NPD6166	Phase 2
0.6727	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3847	Discontinued
0.6713	Remote Similarity	NPD1203	Approved
0.6711	Remote Similarity	NPD5688	Approved
0.6711	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5689	Approved
0.6708	Remote Similarity	NPD4965	Approved
0.6708	Remote Similarity	NPD4967	Phase 2
0.6708	Remote Similarity	NPD4966	Approved
0.6707	Remote Similarity	NPD5710	Approved
0.6707	Remote Similarity	NPD5711	Approved
0.6707	Remote Similarity	NPD7054	Approved
0.6692	Remote Similarity	NPD5451	Approved
0.669	Remote Similarity	NPD3685	Discontinued
0.6689	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2346	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