NPASS Compound

Structure

NPC202886 OpenBabel07101718192D 32 33 0 0 1 0 0 0 0 0999 V2000 1.1340 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4641 -2.0000 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 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2679 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 -0.5000 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 3.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 -1.5000 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 -3.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2679 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 -1.5000 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 2.8660 -0.5000 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 -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 2.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 16 2 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 26 1 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 19 6 1 1 0 0 0 19 22 1 0 0 0 0 19 30 1 0 0 0 0 20 26 1 6 0 0 0 21 27 2 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 1 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 29 1 6 0 0 0 24 31 1 1 0 0 0 25 30 1 0 0 0 0 25 32 1 1 0 0 0 26 7 1 6 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.3
Volume:	483.335
LogP:	6.05
LogD:	4.203
LogS:	-4.742
# Rotatable Bonds:	9
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	4.754
Fsp3:	0.731
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:	-4.675
MDCK Permeability:	2.140597098332364e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.178

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	87.14415740966797%
Volume Distribution (VD):	2.233
Pgp-substrate:	7.549870014190674%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.224
CYP2C19-inhibitor:	0.243
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.615
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.626
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	7.115
Half-life (T1/2):	0.137

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.894
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.95
Carcinogencity:	0.062
Eye Corrosion:	0.021
Eye Irritation:	0.103
Respiratory Toxicity:	0.892

Download Data

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

Natural Product: NPC202886

Natural Product ID:	NPC202886
*Common Name:**	Rel-O-3'-Senecioyl Alpha-Bisabolol Beta-D-Fucopyranoside
IUPAC Name:	[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-methyl-6-[(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-yl]oxyoxan-4-yl] 3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	HEVSYGGJPULUNF-SVCOBJLLSA-N
Standard InCHI:	InChI=1S/C26H42O6/c1-16(2)9-8-14-26(7,20-12-10-18(5)11-13-20)32-25-23(29)24(22(28)19(6)30-25)31-21(27)15-17(3)4/h9-10,15,19-20,22-25,28-29H,8,11-14H2,1-7H3/t19-,20-,22+,23-,24+,25+,26+/m1/s1
SMILES:	CC(=CCC[C@@](C)([C@@H]1CC=C(C)CC1)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](C)O1)O)OC(=O)C=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023565
PubChem CID:	57380393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO32613	carthamus glaucus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22309250]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	IC50	=	110000.0	nM	PMID[468079]
NPT2	Others	Unspecified		IC50	=	60000.0	nM	PMID[468079]

☑ 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 NPC202886 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	189
0.1-0.2	1238
0.2-0.3	4770
0.3-0.4	10669
0.4-0.5	12478
0.5-0.6	7659
0.6-0.7	4756
0.7-0.8	866
0.8-0.85	56
0.85-0.9	13
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC477748
0.9651	High Similarity	NPC477749
0.8953	High Similarity	NPC477746
0.8953	High Similarity	NPC477747
0.8837	High Similarity	NPC266718
0.881	High Similarity	NPC100697
0.871	High Similarity	NPC239547
0.871	High Similarity	NPC309503
0.871	High Similarity	NPC91197
0.871	High Similarity	NPC125551
0.871	High Similarity	NPC96597
0.871	High Similarity	NPC155319
0.8681	High Similarity	NPC238090
0.8681	High Similarity	NPC472196
0.8681	High Similarity	NPC472195
0.8652	High Similarity	NPC248312
0.8587	High Similarity	NPC159698
0.8523	High Similarity	NPC471494
0.8438	Intermediate Similarity	NPC280991
0.8427	Intermediate Similarity	NPC311163
0.8409	Intermediate Similarity	NPC475035
0.8391	Intermediate Similarity	NPC20072
0.8387	Intermediate Similarity	NPC178949
0.8387	Intermediate Similarity	NPC96736
0.8351	Intermediate Similarity	NPC201191
0.8333	Intermediate Similarity	NPC130792
0.8283	Intermediate Similarity	NPC239961
0.828	Intermediate Similarity	NPC474792
0.828	Intermediate Similarity	NPC67398
0.828	Intermediate Similarity	NPC320089
0.828	Intermediate Similarity	NPC91654
0.8276	Intermediate Similarity	NPC469469
0.8247	Intermediate Similarity	NPC198992
0.8191	Intermediate Similarity	NPC2003
0.8191	Intermediate Similarity	NPC25701
0.8191	Intermediate Similarity	NPC256368
0.8172	Intermediate Similarity	NPC302584
0.8161	Intermediate Similarity	NPC163362
0.8161	Intermediate Similarity	NPC127295
0.8152	Intermediate Similarity	NPC309310
0.8132	Intermediate Similarity	NPC475037
0.81	Intermediate Similarity	NPC82251
0.8085	Intermediate Similarity	NPC474835
0.8081	Intermediate Similarity	NPC151516
0.8065	Intermediate Similarity	NPC118078
0.8061	Intermediate Similarity	NPC475157
0.8061	Intermediate Similarity	NPC57586
0.8061	Intermediate Similarity	NPC471637
0.8061	Intermediate Similarity	NPC154132
0.8061	Intermediate Similarity	NPC2313
0.8061	Intermediate Similarity	NPC475655
0.8041	Intermediate Similarity	NPC198422
0.8041	Intermediate Similarity	NPC40182
0.8039	Intermediate Similarity	NPC206618
0.8022	Intermediate Similarity	NPC470836
0.8021	Intermediate Similarity	NPC54731
0.8021	Intermediate Similarity	NPC143446
0.8	Intermediate Similarity	NPC294293
0.798	Intermediate Similarity	NPC121423
0.7979	Intermediate Similarity	NPC472197
0.7979	Intermediate Similarity	NPC472199
0.7959	Intermediate Similarity	NPC477721
0.7959	Intermediate Similarity	NPC477716
0.7957	Intermediate Similarity	NPC133450
0.7941	Intermediate Similarity	NPC219900
0.7941	Intermediate Similarity	NPC38948
0.7941	Intermediate Similarity	NPC392
0.7941	Intermediate Similarity	NPC177524
0.7935	Intermediate Similarity	NPC316138
0.7935	Intermediate Similarity	NPC313658
0.7917	Intermediate Similarity	NPC108141
0.7912	Intermediate Similarity	NPC475034
0.7912	Intermediate Similarity	NPC470124
0.7907	Intermediate Similarity	NPC229655
0.7905	Intermediate Similarity	NPC287075
0.7905	Intermediate Similarity	NPC473159
0.79	Intermediate Similarity	NPC197736
0.7895	Intermediate Similarity	NPC61201
0.7889	Intermediate Similarity	NPC31019
0.7889	Intermediate Similarity	NPC27314
0.7889	Intermediate Similarity	NPC231601
0.7889	Intermediate Similarity	NPC2379
0.7889	Intermediate Similarity	NPC106912
0.7889	Intermediate Similarity	NPC263087
0.7879	Intermediate Similarity	NPC477717
0.7872	Intermediate Similarity	NPC3952
0.7872	Intermediate Similarity	NPC6414
0.7872	Intermediate Similarity	NPC327253
0.7872	Intermediate Similarity	NPC177668
0.7872	Intermediate Similarity	NPC303451
0.7872	Intermediate Similarity	NPC471569
0.7857	Intermediate Similarity	NPC472015
0.7857	Intermediate Similarity	NPC65700
0.7857	Intermediate Similarity	NPC169468
0.7857	Intermediate Similarity	NPC307517
0.7857	Intermediate Similarity	NPC61630
0.7857	Intermediate Similarity	NPC81483
0.785	Intermediate Similarity	NPC203862
0.7843	Intermediate Similarity	NPC472390
0.783	Intermediate Similarity	NPC31354
0.783	Intermediate Similarity	NPC84949
0.783	Intermediate Similarity	NPC471633
0.783	Intermediate Similarity	NPC69576
0.7826	Intermediate Similarity	NPC208473
0.7822	Intermediate Similarity	NPC470768
0.7816	Intermediate Similarity	NPC40049
0.7812	Intermediate Similarity	NPC472198
0.7812	Intermediate Similarity	NPC211238
0.781	Intermediate Similarity	NPC328074
0.781	Intermediate Similarity	NPC317460
0.781	Intermediate Similarity	NPC321272
0.781	Intermediate Similarity	NPC470025
0.7802	Intermediate Similarity	NPC166279
0.7802	Intermediate Similarity	NPC473308
0.78	Intermediate Similarity	NPC223834
0.78	Intermediate Similarity	NPC470571
0.78	Intermediate Similarity	NPC472815
0.7788	Intermediate Similarity	NPC316708
0.7778	Intermediate Similarity	NPC324841
0.7778	Intermediate Similarity	NPC79631
0.7778	Intermediate Similarity	NPC251026
0.7767	Intermediate Similarity	NPC48548
0.7767	Intermediate Similarity	NPC217921
0.7767	Intermediate Similarity	NPC135015
0.7767	Intermediate Similarity	NPC128795
0.7766	Intermediate Similarity	NPC470734
0.7757	Intermediate Similarity	NPC193382
0.7757	Intermediate Similarity	NPC310341
0.7757	Intermediate Similarity	NPC199428
0.7757	Intermediate Similarity	NPC207637
0.7757	Intermediate Similarity	NPC99620
0.7757	Intermediate Similarity	NPC5311
0.7755	Intermediate Similarity	NPC477719
0.7755	Intermediate Similarity	NPC477718
0.7755	Intermediate Similarity	NPC474182
0.7755	Intermediate Similarity	NPC98112
0.7745	Intermediate Similarity	NPC315070
0.7745	Intermediate Similarity	NPC85670
0.7745	Intermediate Similarity	NPC470763
0.7745	Intermediate Similarity	NPC470767
0.7742	Intermediate Similarity	NPC471055
0.7742	Intermediate Similarity	NPC118077
0.7742	Intermediate Similarity	NPC471056
0.7742	Intermediate Similarity	NPC475186
0.7736	Intermediate Similarity	NPC470027
0.7732	Intermediate Similarity	NPC240838
0.7732	Intermediate Similarity	NPC230347
0.7732	Intermediate Similarity	NPC275310
0.7732	Intermediate Similarity	NPC469543
0.7732	Intermediate Similarity	NPC286612
0.7727	Intermediate Similarity	NPC477089
0.7723	Intermediate Similarity	NPC120009
0.7723	Intermediate Similarity	NPC281378
0.7717	Intermediate Similarity	NPC163606
0.7717	Intermediate Similarity	NPC470658
0.7714	Intermediate Similarity	NPC17791
0.7714	Intermediate Similarity	NPC470026
0.7708	Intermediate Similarity	NPC320552
0.7701	Intermediate Similarity	NPC469880
0.7701	Intermediate Similarity	NPC326661
0.77	Intermediate Similarity	NPC285231
0.77	Intermediate Similarity	NPC11974
0.77	Intermediate Similarity	NPC154127
0.77	Intermediate Similarity	NPC219038
0.77	Intermediate Similarity	NPC21568
0.77	Intermediate Similarity	NPC472554
0.7692	Intermediate Similarity	NPC133625
0.7692	Intermediate Similarity	NPC473315
0.7692	Intermediate Similarity	NPC142111
0.7692	Intermediate Similarity	NPC316974
0.7692	Intermediate Similarity	NPC40728
0.7692	Intermediate Similarity	NPC44261
0.7685	Intermediate Similarity	NPC142066
0.7685	Intermediate Similarity	NPC471354
0.7685	Intermediate Similarity	NPC34390
0.7685	Intermediate Similarity	NPC152615
0.7685	Intermediate Similarity	NPC196429
0.7685	Intermediate Similarity	NPC471351
0.7685	Intermediate Similarity	NPC77319
0.7685	Intermediate Similarity	NPC290693
0.7685	Intermediate Similarity	NPC309034
0.7685	Intermediate Similarity	NPC471355
0.7685	Intermediate Similarity	NPC99728
0.7685	Intermediate Similarity	NPC50305
0.7685	Intermediate Similarity	NPC84987
0.7685	Intermediate Similarity	NPC244402
0.7685	Intermediate Similarity	NPC87250
0.7685	Intermediate Similarity	NPC93883
0.7685	Intermediate Similarity	NPC158344
0.7685	Intermediate Similarity	NPC243196
0.7685	Intermediate Similarity	NPC157376
0.7685	Intermediate Similarity	NPC27507
0.7685	Intermediate Similarity	NPC471353
0.7685	Intermediate Similarity	NPC473852
0.7685	Intermediate Similarity	NPC474418
0.7677	Intermediate Similarity	NPC203627
0.7677	Intermediate Similarity	NPC70733
0.7677	Intermediate Similarity	NPC477928
0.7677	Intermediate Similarity	NPC56071
0.767	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 NPC202886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1578
0.2-0.3	3981
0.3-0.4	2314
0.4-0.5	700
0.5-0.6	328
0.6-0.7	76
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7941	Intermediate Similarity	NPD6686	Approved
0.7872	Intermediate Similarity	NPD46	Approved
0.7872	Intermediate Similarity	NPD6698	Approved
0.7857	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD7328	Approved
0.7615	Intermediate Similarity	NPD7327	Approved
0.7609	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7503	Approved
0.7545	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD7838	Discovery
0.7477	Intermediate Similarity	NPD8294	Approved
0.7477	Intermediate Similarity	NPD8377	Approved
0.7411	Intermediate Similarity	NPD8296	Approved
0.7411	Intermediate Similarity	NPD8380	Approved
0.7411	Intermediate Similarity	NPD8335	Approved
0.7411	Intermediate Similarity	NPD8379	Approved
0.7411	Intermediate Similarity	NPD8378	Approved
0.7411	Intermediate Similarity	NPD8033	Approved
0.7353	Intermediate Similarity	NPD5344	Discontinued
0.7333	Intermediate Similarity	NPD6412	Phase 2
0.7257	Intermediate Similarity	NPD8517	Approved
0.7257	Intermediate Similarity	NPD8515	Approved
0.7257	Intermediate Similarity	NPD8513	Phase 3
0.7257	Intermediate Similarity	NPD8516	Approved
0.7155	Intermediate Similarity	NPD7507	Approved
0.7064	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7319	Approved
0.6923	Remote Similarity	NPD6648	Approved
0.6827	Remote Similarity	NPD7638	Approved
0.6786	Remote Similarity	NPD8133	Approved
0.6762	Remote Similarity	NPD7640	Approved
0.6762	Remote Similarity	NPD7639	Approved
0.6744	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7983	Approved
0.6727	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6053	Discontinued
0.6695	Remote Similarity	NPD7829	Approved
0.6695	Remote Similarity	NPD8328	Phase 3
0.6695	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6598	Remote Similarity	NPD6110	Phase 1
0.6555	Remote Similarity	NPD7642	Approved
0.6505	Remote Similarity	NPD5779	Approved
0.6505	Remote Similarity	NPD5778	Approved
0.6465	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8451	Approved
0.641	Remote Similarity	NPD7641	Discontinued
0.6408	Remote Similarity	NPD7637	Suspended
0.6395	Remote Similarity	NPD368	Approved
0.6393	Remote Similarity	NPD8448	Approved
0.6393	Remote Similarity	NPD8293	Discontinued
0.6387	Remote Similarity	NPD8444	Approved
0.6372	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7736	Approved
0.6337	Remote Similarity	NPD7524	Approved
0.6337	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD4251	Approved
0.6333	Remote Similarity	NPD6370	Approved
0.6325	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7115	Discovery
0.6321	Remote Similarity	NPD7839	Suspended
0.6289	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4819	Approved
0.6289	Remote Similarity	NPD4821	Approved
0.6289	Remote Similarity	NPD4822	Approved
0.6289	Remote Similarity	NPD4820	Approved
0.624	Remote Similarity	NPD8390	Approved
0.624	Remote Similarity	NPD8392	Approved
0.624	Remote Similarity	NPD8391	Approved
0.6238	Remote Similarity	NPD4249	Approved
0.623	Remote Similarity	NPD8299	Approved
0.623	Remote Similarity	NPD7492	Approved
0.623	Remote Similarity	NPD8342	Approved
0.623	Remote Similarity	NPD8341	Approved
0.623	Remote Similarity	NPD8340	Approved
0.6214	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6051	Approved
0.6214	Remote Similarity	NPD6101	Approved
0.6202	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6009	Approved
0.6182	Remote Similarity	NPD7632	Discontinued
0.6179	Remote Similarity	NPD6616	Approved
0.6167	Remote Similarity	NPD6059	Approved
0.6167	Remote Similarity	NPD6054	Approved
0.6154	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7078	Approved
0.6121	Remote Similarity	NPD6882	Approved
0.6111	Remote Similarity	NPD6083	Phase 2
0.6111	Remote Similarity	NPD6084	Phase 2
0.6106	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6695	Phase 3
0.61	Remote Similarity	NPD7154	Phase 3
0.6095	Remote Similarity	NPD6411	Approved
0.6082	Remote Similarity	NPD4271	Approved
0.6082	Remote Similarity	NPD4268	Approved
0.6068	Remote Similarity	NPD4632	Approved
0.6066	Remote Similarity	NPD8080	Discontinued
0.605	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6319	Approved
0.6029	Remote Similarity	NPD7625	Phase 1
0.6019	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD4211	Phase 1
0.6018	Remote Similarity	NPD5739	Approved
0.6018	Remote Similarity	NPD6675	Approved
0.6018	Remote Similarity	NPD7128	Approved
0.6018	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD6435	Approved
0.6	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3168	Discontinued
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.5983	Remote Similarity	NPD8297	Approved
0.5981	Remote Similarity	NPD5282	Discontinued
0.5981	Remote Similarity	NPD7748	Approved
0.598	Remote Similarity	NPD1694	Approved
0.5963	Remote Similarity	NPD7902	Approved
0.596	Remote Similarity	NPD7332	Phase 2
0.596	Remote Similarity	NPD7514	Phase 3
0.5943	Remote Similarity	NPD7515	Phase 2
0.5941	Remote Similarity	NPD3669	Approved
0.5941	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5362	Discontinued
0.5935	Remote Similarity	NPD5988	Approved
0.5926	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5695	Phase 3
0.5918	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7505	Discontinued
0.5913	Remote Similarity	NPD6881	Approved
0.5913	Remote Similarity	NPD7320	Approved
0.5913	Remote Similarity	NPD6899	Approved
0.5905	Remote Similarity	NPD1695	Approved
0.5889	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6399	Phase 3
0.5865	Remote Similarity	NPD7750	Discontinued
0.5862	Remote Similarity	NPD6373	Approved
0.5862	Remote Similarity	NPD6372	Approved
0.5854	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5209	Approved
0.5833	Remote Similarity	NPD1811	Approved
0.5833	Remote Similarity	NPD1810	Approved
0.5827	Remote Similarity	NPD8337	Approved
0.5827	Remote Similarity	NPD8336	Approved
0.5826	Remote Similarity	NPD5701	Approved
0.5826	Remote Similarity	NPD5697	Approved
0.5825	Remote Similarity	NPD5363	Approved
0.5816	Remote Similarity	NPD6925	Approved
0.5816	Remote Similarity	NPD6932	Approved
0.5816	Remote Similarity	NPD5776	Phase 2
0.5814	Remote Similarity	NPD7260	Phase 2
0.5812	Remote Similarity	NPD7102	Approved
0.5812	Remote Similarity	NPD7290	Approved
0.5812	Remote Similarity	NPD6883	Approved
0.5806	Remote Similarity	NPD5126	Approved
0.5806	Remote Similarity	NPD5125	Phase 3
0.58	Remote Similarity	NPD5368	Approved
0.58	Remote Similarity	NPD6930	Phase 2
0.58	Remote Similarity	NPD6931	Approved
0.5794	Remote Similarity	NPD8273	Phase 1
0.5785	Remote Similarity	NPD7500	Approved
0.5784	Remote Similarity	NPD5331	Approved
0.5784	Remote Similarity	NPD5332	Approved
0.5773	Remote Similarity	NPD8264	Approved
0.5773	Remote Similarity	NPD8039	Approved
0.5769	Remote Similarity	NPD7521	Approved
0.5769	Remote Similarity	NPD7334	Approved
0.5769	Remote Similarity	NPD6409	Approved
0.5769	Remote Similarity	NPD5330	Approved
0.5769	Remote Similarity	NPD6684	Approved
0.5769	Remote Similarity	NPD7146	Approved
0.5766	Remote Similarity	NPD5696	Approved
0.5763	Remote Similarity	NPD8130	Phase 1
0.5763	Remote Similarity	NPD6869	Approved
0.5763	Remote Similarity	NPD6847	Approved
0.5763	Remote Similarity	NPD6650	Approved
0.5763	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6649	Approved
0.5763	Remote Similarity	NPD6617	Approved
0.576	Remote Similarity	NPD7604	Phase 2
0.5758	Remote Similarity	NPD7145	Approved
0.5743	Remote Similarity	NPD6898	Phase 1
0.5743	Remote Similarity	NPD5369	Approved
0.5743	Remote Similarity	NPD6902	Approved
0.5743	Remote Similarity	NPD4790	Discontinued
0.5739	Remote Similarity	NPD6640	Phase 3
0.5726	Remote Similarity	NPD5983	Phase 2
0.5726	Remote Similarity	NPD6014	Approved
0.5726	Remote Similarity	NPD6013	Approved
0.5726	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6933	Approved
0.5703	Remote Similarity	NPD6033	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