NPASS Compound

Structure

NPC96597 OpenBabel07101718312D 34 36 0 0 1 0 0 0 0 0999 V2000 1.1340 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0000 3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5981 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 -1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 9 27 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 18 3 1 6 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 29 2 0 0 0 0 19 33 1 0 0 0 0 20 28 1 6 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 24 1 0 0 0 0 22 30 1 6 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 24 33 1 6 0 0 0 25 32 1 0 0 0 0 25 34 1 6 0 0 0 27 7 1 1 0 0 0 27 34 1 0 0 0 0 28 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.33
Volume:	512.007
LogP:	4.951
LogD:	3.957
LogS:	-4.891
# Rotatable Bonds:	8
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.399
Synthetic Accessibility Score:	4.995
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.68
MDCK Permeability:	2.16151984204771e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.193
Human Intestinal Absorption (HIA):	0.112
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.049

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	90.81713104248047%
Volume Distribution (VD):	2.361
Pgp-substrate:	6.818767547607422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.204
CYP2C9-substrate:	0.12
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.267
CYP3A4-inhibitor:	0.781
CYP3A4-substrate:	0.323

ADMET: Excretion

Clearance (CL):	1.843
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.266
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.524
Carcinogencity:	0.055
Eye Corrosion:	0.023
Eye Irritation:	0.036
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC96597

Natural Product ID:	NPC96597
*Common Name:**	(13R)-Labda-7,14-Diene 13-O-Beta-D-(3'-O-Acetyl)Fucopyranoside
IUPAC Name:	[(2S,3R,4S,5S,6R)-2-[(3R)-5-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-1-en-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate
Synonyms:
Standard InCHIKey:	WWGDINVWMUFHKK-QNKMPZKGSA-N
Standard InCHI:	InChI=1S/C28H46O6/c1-9-27(7,34-25-23(31)24(33-19(4)29)22(30)18(3)32-25)16-13-20-17(2)11-12-21-26(5,6)14-10-15-28(20,21)8/h9,11,18,20-25,30-31H,1,10,12-16H2,2-8H3/t18-,20+,21+,22+,23-,24+,25+,27+,28-/m1/s1
SMILES:	C=C[C@](O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O)OC(=O)C)O)(CC[C@H]1C(=CC[C@@H]2[C@]1(C)CCCC2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463564
PubChem CID:	11712695
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO3386	Aster spathulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252909]
NPO3386	Aster spathulifolius	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17121178]
NPO3386	Aster spathulifolius	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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.6	ug ml-1	PMID[485015]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	3.8	ug ml-1	PMID[485015]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.5	ug ml-1	PMID[485015]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	5.1	ug ml-1	PMID[485015]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	3.8	ug ml-1	PMID[485015]

☑ 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 NPC96597 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	203
0.1-0.2	1319
0.2-0.3	4439
0.3-0.4	10376
0.4-0.5	11292
0.5-0.6	7171
0.6-0.7	5596
0.7-0.8	2169
0.8-0.85	102
0.85-0.9	19
0.9-0.95	1
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC309503
1.0	High Similarity	NPC155319
1.0	High Similarity	NPC91197
1.0	High Similarity	NPC125551
1.0	High Similarity	NPC239547
0.9556	High Similarity	NPC91654
0.9556	High Similarity	NPC474792
0.9556	High Similarity	NPC67398
0.9468	High Similarity	NPC280991
0.9341	High Similarity	NPC474835
0.9032	High Similarity	NPC178949
0.9032	High Similarity	NPC96736
0.9022	High Similarity	NPC302584
0.8936	High Similarity	NPC275310
0.8936	High Similarity	NPC286612
0.8936	High Similarity	NPC230347
0.8889	High Similarity	NPC470763
0.8889	High Similarity	NPC470767
0.883	High Similarity	NPC211238
0.8776	High Similarity	NPC154452
0.8776	High Similarity	NPC470571
0.871	High Similarity	NPC202886
0.8673	High Similarity	NPC21064
0.8673	High Similarity	NPC121072
0.8673	High Similarity	NPC285231
0.8673	High Similarity	NPC21568
0.8667	High Similarity	NPC166279
0.866	High Similarity	NPC477928
0.8632	High Similarity	NPC305160
0.8614	High Similarity	NPC472390
0.8602	High Similarity	NPC473058
0.8602	High Similarity	NPC309310
0.8602	High Similarity	NPC477748
0.86	High Similarity	NPC470768
0.8558	High Similarity	NPC473125
0.8557	High Similarity	NPC98112
0.8529	High Similarity	NPC217921
0.8529	High Similarity	NPC128795
0.8529	High Similarity	NPC135015
0.8529	High Similarity	NPC48548
0.8515	High Similarity	NPC82251
0.8515	High Similarity	NPC239961
0.8511	High Similarity	NPC474249
0.8511	High Similarity	NPC261990
0.8511	High Similarity	NPC159876
0.8495	Intermediate Similarity	NPC248312
0.8485	Intermediate Similarity	NPC198992
0.8476	Intermediate Similarity	NPC49413
0.8476	Intermediate Similarity	NPC473159
0.8476	Intermediate Similarity	NPC44298
0.8476	Intermediate Similarity	NPC473128
0.8476	Intermediate Similarity	NPC290608
0.8476	Intermediate Similarity	NPC40133
0.8454	Intermediate Similarity	NPC90583
0.8447	Intermediate Similarity	NPC316974
0.8447	Intermediate Similarity	NPC40728
0.8431	Intermediate Similarity	NPC88013
0.8431	Intermediate Similarity	NPC125423
0.8431	Intermediate Similarity	NPC33053
0.8421	Intermediate Similarity	NPC477749
0.8416	Intermediate Similarity	NPC31430
0.8416	Intermediate Similarity	NPC85593
0.8416	Intermediate Similarity	NPC173583
0.84	Intermediate Similarity	NPC238397
0.84	Intermediate Similarity	NPC471363
0.8384	Intermediate Similarity	NPC477716
0.8384	Intermediate Similarity	NPC477721
0.837	Intermediate Similarity	NPC477747
0.837	Intermediate Similarity	NPC477746
0.8367	Intermediate Similarity	NPC240372
0.8365	Intermediate Similarity	NPC83005
0.835	Intermediate Similarity	NPC311223
0.835	Intermediate Similarity	NPC177524
0.835	Intermediate Similarity	NPC392
0.835	Intermediate Similarity	NPC219900
0.8333	Intermediate Similarity	NPC473199
0.8317	Intermediate Similarity	NPC127933
0.8317	Intermediate Similarity	NPC473124
0.8317	Intermediate Similarity	NPC473123
0.8317	Intermediate Similarity	NPC134270
0.8317	Intermediate Similarity	NPC475889
0.8317	Intermediate Similarity	NPC7644
0.8317	Intermediate Similarity	NPC7613
0.8302	Intermediate Similarity	NPC293658
0.8302	Intermediate Similarity	NPC75167
0.8302	Intermediate Similarity	NPC474410
0.8302	Intermediate Similarity	NPC311592
0.83	Intermediate Similarity	NPC477717
0.83	Intermediate Similarity	NPC154127
0.8283	Intermediate Similarity	NPC158088
0.828	Intermediate Similarity	NPC470836
0.8269	Intermediate Similarity	NPC206618
0.8265	Intermediate Similarity	NPC207617
0.8252	Intermediate Similarity	NPC293512
0.8247	Intermediate Similarity	NPC477927
0.8247	Intermediate Similarity	NPC72817
0.8241	Intermediate Similarity	NPC203862
0.8235	Intermediate Similarity	NPC81567
0.8235	Intermediate Similarity	NPC93352
0.8235	Intermediate Similarity	NPC203354
0.8235	Intermediate Similarity	NPC201880
0.8235	Intermediate Similarity	NPC470321
0.8235	Intermediate Similarity	NPC264867
0.8235	Intermediate Similarity	NPC473127
0.8235	Intermediate Similarity	NPC110656
0.8235	Intermediate Similarity	NPC473207
0.8229	Intermediate Similarity	NPC289361
0.8224	Intermediate Similarity	NPC181145
0.8224	Intermediate Similarity	NPC69576
0.8224	Intermediate Similarity	NPC471633
0.8224	Intermediate Similarity	NPC31354
0.8224	Intermediate Similarity	NPC84949
0.8222	Intermediate Similarity	NPC100697
0.8218	Intermediate Similarity	NPC121423
0.8218	Intermediate Similarity	NPC201191
0.8208	Intermediate Similarity	NPC321272
0.8208	Intermediate Similarity	NPC470025
0.8208	Intermediate Similarity	NPC317460
0.8208	Intermediate Similarity	NPC328074
0.82	Intermediate Similarity	NPC477971
0.82	Intermediate Similarity	NPC228251
0.82	Intermediate Similarity	NPC477972
0.82	Intermediate Similarity	NPC469942
0.82	Intermediate Similarity	NPC161527
0.82	Intermediate Similarity	NPC20113
0.82	Intermediate Similarity	NPC477968
0.82	Intermediate Similarity	NPC219285
0.82	Intermediate Similarity	NPC64348
0.819	Intermediate Similarity	NPC316708
0.819	Intermediate Similarity	NPC191439
0.819	Intermediate Similarity	NPC119550
0.819	Intermediate Similarity	NPC170974
0.819	Intermediate Similarity	NPC103627
0.8182	Intermediate Similarity	NPC471770
0.8182	Intermediate Similarity	NPC473890
0.8182	Intermediate Similarity	NPC243728
0.8182	Intermediate Similarity	NPC278939
0.8182	Intermediate Similarity	NPC477719
0.8182	Intermediate Similarity	NPC477718
0.8182	Intermediate Similarity	NPC473555
0.8173	Intermediate Similarity	NPC38948
0.8173	Intermediate Similarity	NPC472988
0.8173	Intermediate Similarity	NPC295980
0.8173	Intermediate Similarity	NPC38376
0.8173	Intermediate Similarity	NPC295389
0.8173	Intermediate Similarity	NPC80210
0.8173	Intermediate Similarity	NPC38217
0.8163	Intermediate Similarity	NPC471362
0.8163	Intermediate Similarity	NPC472189
0.8163	Intermediate Similarity	NPC108141
0.8163	Intermediate Similarity	NPC471372
0.8155	Intermediate Similarity	NPC252296
0.8155	Intermediate Similarity	NPC162033
0.8152	Intermediate Similarity	NPC49208
0.8152	Intermediate Similarity	NPC23748
0.8148	Intermediate Similarity	NPC5311
0.8148	Intermediate Similarity	NPC310341
0.8148	Intermediate Similarity	NPC207637
0.8148	Intermediate Similarity	NPC193382
0.8148	Intermediate Similarity	NPC199428
0.8148	Intermediate Similarity	NPC99620
0.8137	Intermediate Similarity	NPC281378
0.8131	Intermediate Similarity	NPC470027
0.8119	Intermediate Similarity	NPC11974
0.8119	Intermediate Similarity	NPC475617
0.8119	Intermediate Similarity	NPC267510
0.8119	Intermediate Similarity	NPC470434
0.8113	Intermediate Similarity	NPC17791
0.8113	Intermediate Similarity	NPC65034
0.8113	Intermediate Similarity	NPC470026
0.8113	Intermediate Similarity	NPC208189
0.81	Intermediate Similarity	NPC157739
0.81	Intermediate Similarity	NPC56071
0.81	Intermediate Similarity	NPC5358
0.81	Intermediate Similarity	NPC198422
0.81	Intermediate Similarity	NPC216260
0.81	Intermediate Similarity	NPC40182
0.81	Intermediate Similarity	NPC70733
0.81	Intermediate Similarity	NPC312325
0.8095	Intermediate Similarity	NPC237503
0.8095	Intermediate Similarity	NPC285253
0.8095	Intermediate Similarity	NPC43976
0.8095	Intermediate Similarity	NPC473318
0.8095	Intermediate Similarity	NPC51925
0.8095	Intermediate Similarity	NPC296761
0.8095	Intermediate Similarity	NPC167383
0.8095	Intermediate Similarity	NPC473328
0.8095	Intermediate Similarity	NPC57362
0.8095	Intermediate Similarity	NPC154085
0.8095	Intermediate Similarity	NPC195116
0.8095	Intermediate Similarity	NPC306746
0.8095	Intermediate Similarity	NPC137917
0.8095	Intermediate Similarity	NPC28844
0.8095	Intermediate Similarity	NPC204407
0.8095	Intermediate Similarity	NPC221110
0.8095	Intermediate Similarity	NPC180459
0.8095	Intermediate Similarity	NPC125361
0.8081	Intermediate Similarity	NPC171598
0.8077	Intermediate Similarity	NPC281939
0.8077	Intermediate Similarity	NPC109376

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 NPC96597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1524
0.2-0.3	3889
0.3-0.4	2280
0.4-0.5	805
0.5-0.6	271
0.6-0.7	183
0.7-0.8	20
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.835	Intermediate Similarity	NPD6686	Approved
0.8108	Intermediate Similarity	NPD7503	Approved
0.8	Intermediate Similarity	NPD7328	Approved
0.8	Intermediate Similarity	NPD7327	Approved
0.7928	Intermediate Similarity	NPD7516	Approved
0.7905	Intermediate Similarity	NPD6412	Phase 2
0.7857	Intermediate Similarity	NPD8294	Approved
0.7857	Intermediate Similarity	NPD8377	Approved
0.7788	Intermediate Similarity	NPD8380	Approved
0.7788	Intermediate Similarity	NPD8296	Approved
0.7788	Intermediate Similarity	NPD8379	Approved
0.7788	Intermediate Similarity	NPD8033	Approved
0.7788	Intermediate Similarity	NPD8335	Approved
0.7788	Intermediate Similarity	NPD8378	Approved
0.7636	Intermediate Similarity	NPD8133	Approved
0.7593	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7507	Approved
0.7333	Intermediate Similarity	NPD7319	Approved
0.7264	Intermediate Similarity	NPD5344	Discontinued
0.7238	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7638	Approved
0.7203	Intermediate Similarity	NPD8328	Phase 3
0.7182	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8513	Phase 3
0.7179	Intermediate Similarity	NPD8516	Approved
0.7179	Intermediate Similarity	NPD8515	Approved
0.7179	Intermediate Similarity	NPD8517	Approved
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD7838	Discovery
0.6975	Remote Similarity	NPD6370	Approved
0.6967	Remote Similarity	NPD7736	Approved
0.6961	Remote Similarity	NPD6051	Approved
0.6931	Remote Similarity	NPD7524	Approved
0.6916	Remote Similarity	NPD4225	Approved
0.6885	Remote Similarity	NPD8293	Discontinued
0.686	Remote Similarity	NPD7492	Approved
0.6852	Remote Similarity	NPD6648	Approved
0.6838	Remote Similarity	NPD7115	Discovery
0.6838	Remote Similarity	NPD6009	Approved
0.6827	Remote Similarity	NPD6411	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6803	Remote Similarity	NPD6616	Approved
0.68	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6882	Approved
0.6762	Remote Similarity	NPD6399	Phase 3
0.6754	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7078	Approved
0.6724	Remote Similarity	NPD4632	Approved
0.67	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6638	Remote Similarity	NPD6053	Discontinued
0.6638	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6101	Approved
0.6633	Remote Similarity	NPD7645	Phase 2
0.6613	Remote Similarity	NPD8074	Phase 3
0.6612	Remote Similarity	NPD6015	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.6604	Remote Similarity	NPD5778	Approved
0.6604	Remote Similarity	NPD5779	Approved
0.6579	Remote Similarity	NPD6899	Approved
0.6579	Remote Similarity	NPD6881	Approved
0.6577	Remote Similarity	NPD7632	Discontinued
0.6566	Remote Similarity	NPD7525	Registered
0.6557	Remote Similarity	NPD5988	Approved
0.6549	Remote Similarity	NPD5739	Approved
0.6549	Remote Similarity	NPD6402	Approved
0.6549	Remote Similarity	NPD7128	Approved
0.6549	Remote Similarity	NPD6675	Approved
0.6542	Remote Similarity	NPD7748	Approved
0.6535	Remote Similarity	NPD3669	Approved
0.6535	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7902	Approved
0.6509	Remote Similarity	NPD7515	Phase 2
0.6509	Remote Similarity	NPD7983	Approved
0.6504	Remote Similarity	NPD6067	Discontinued
0.6491	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5697	Approved
0.6481	Remote Similarity	NPD5695	Phase 3
0.6475	Remote Similarity	NPD6921	Approved
0.6466	Remote Similarity	NPD6371	Approved
0.6466	Remote Similarity	NPD6883	Approved
0.6466	Remote Similarity	NPD7290	Approved
0.6466	Remote Similarity	NPD7102	Approved
0.6458	Remote Similarity	NPD1810	Approved
0.6458	Remote Similarity	NPD1811	Approved
0.6442	Remote Similarity	NPD7750	Discontinued
0.6435	Remote Similarity	NPD7320	Approved
0.641	Remote Similarity	NPD6869	Approved
0.641	Remote Similarity	NPD6650	Approved
0.641	Remote Similarity	NPD6617	Approved
0.641	Remote Similarity	NPD6649	Approved
0.641	Remote Similarity	NPD6847	Approved
0.641	Remote Similarity	NPD8130	Phase 1
0.64	Remote Similarity	NPD6931	Approved
0.64	Remote Similarity	NPD8451	Approved
0.64	Remote Similarity	NPD6930	Phase 2
0.6392	Remote Similarity	NPD7339	Approved
0.6392	Remote Similarity	NPD6942	Approved
0.6379	Remote Similarity	NPD6014	Approved
0.6379	Remote Similarity	NPD6012	Approved
0.6379	Remote Similarity	NPD6373	Approved
0.6379	Remote Similarity	NPD6372	Approved
0.6379	Remote Similarity	NPD6013	Approved
0.6371	Remote Similarity	NPD7604	Phase 2
0.635	Remote Similarity	NPD7625	Phase 1
0.6349	Remote Similarity	NPD8448	Approved
0.6348	Remote Similarity	NPD5701	Approved
0.6346	Remote Similarity	NPD7146	Approved
0.6346	Remote Similarity	NPD6684	Approved
0.6346	Remote Similarity	NPD7334	Approved
0.6346	Remote Similarity	NPD5330	Approved
0.6346	Remote Similarity	NPD6409	Approved
0.6346	Remote Similarity	NPD7521	Approved
0.6341	Remote Similarity	NPD5983	Phase 2
0.6328	Remote Similarity	NPD8390	Approved
0.6328	Remote Similarity	NPD8391	Approved
0.6328	Remote Similarity	NPD8392	Approved
0.6327	Remote Similarity	NPD6933	Approved
0.6327	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4786	Approved
0.6306	Remote Similarity	NPD5696	Approved
0.63	Remote Similarity	NPD6929	Approved
0.6296	Remote Similarity	NPD8171	Discontinued
0.6293	Remote Similarity	NPD6011	Approved
0.629	Remote Similarity	NPD5126	Approved
0.629	Remote Similarity	NPD5125	Phase 3
0.6286	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3667	Approved
0.627	Remote Similarity	NPD6336	Discontinued
0.6263	Remote Similarity	NPD6932	Approved
0.6262	Remote Similarity	NPD3168	Discontinued
0.624	Remote Similarity	NPD7829	Approved
0.624	Remote Similarity	NPD7830	Approved
0.6239	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7900	Approved
0.6238	Remote Similarity	NPD7332	Phase 2
0.6238	Remote Similarity	NPD7514	Phase 3
0.6231	Remote Similarity	NPD8449	Approved
0.6226	Remote Similarity	NPD5737	Approved
0.6226	Remote Similarity	NPD6903	Approved
0.6226	Remote Similarity	NPD6672	Approved
0.6226	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8444	Approved
0.6207	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5284	Approved
0.6204	Remote Similarity	NPD5693	Phase 1
0.6204	Remote Similarity	NPD7087	Discontinued
0.6204	Remote Similarity	NPD5281	Approved
0.6202	Remote Similarity	NPD5956	Approved
0.62	Remote Similarity	NPD7145	Approved
0.619	Remote Similarity	NPD8299	Approved
0.619	Remote Similarity	NPD8341	Approved
0.619	Remote Similarity	NPD8340	Approved
0.619	Remote Similarity	NPD8342	Approved
0.6186	Remote Similarity	NPD4634	Approved
0.6183	Remote Similarity	NPD8450	Suspended
0.6172	Remote Similarity	NPD6033	Approved
0.6168	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD3666	Approved
0.6154	Remote Similarity	NPD3133	Approved
0.6154	Remote Similarity	NPD7260	Phase 2
0.6154	Remote Similarity	NPD3665	Phase 1
0.6146	Remote Similarity	NPD2254	Approved
0.6146	Remote Similarity	NPD2686	Approved
0.6146	Remote Similarity	NPD2687	Approved
0.614	Remote Similarity	NPD5211	Phase 2
0.6139	Remote Similarity	NPD4195	Approved
0.6134	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3573	Approved
0.6132	Remote Similarity	NPD4250	Approved
0.6132	Remote Similarity	NPD4251	Approved
0.6126	Remote Similarity	NPD7839	Suspended
0.6126	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4784	Approved
0.6122	Remote Similarity	NPD6926	Approved
0.6122	Remote Similarity	NPD4785	Approved
0.6122	Remote Similarity	NPD6924	Approved
0.6121	Remote Similarity	NPD6008	Approved
0.6111	Remote Similarity	NPD7642	Approved
0.6106	Remote Similarity	NPD5286	Approved
0.6106	Remote Similarity	NPD4696	Approved
0.6106	Remote Similarity	NPD5285	Approved
0.61	Remote Similarity	NPD6925	Approved
0.61	Remote Similarity	NPD5776	Phase 2
0.6098	Remote Similarity	NPD7641	Discontinued
0.6095	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6893	Approved

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