NPASS Compound

Structure

NPC159692 OpenBabel07101719512D 38 42 0 0 1 0 0 0 0 0999 V2000 1.6701 5.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8214 -1.7210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3051 1.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9510 0.6245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9286 0.9225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5744 -0.1574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0564 3.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7969 1.8653 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 -1.5283 3.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0805 2.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9370 4.4020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 -2.0917 2.8209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3163 1.5553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5633 -0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1490 2.9888 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0441 4.5953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6928 2.3372 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 -0.5311 3.7219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4645 5.5026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0581 3.2680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4640 3.3617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9972 2.0747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1868 -0.7902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7040 2.1881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 36 1 0 0 0 0 7 9 1 0 0 0 0 7 20 2 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 16 2 0 0 0 0 11 23 1 0 0 0 0 12 19 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 29 1 0 0 0 0 14 19 1 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 15 37 1 0 0 0 0 16 25 1 0 0 0 0 17 30 1 6 0 0 0 18 31 2 0 0 0 0 18 38 1 0 0 0 0 20 26 1 0 0 0 0 21 36 1 0 0 0 0 22 24 1 0 0 0 0 22 30 1 6 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 29 1 6 0 0 0 25 28 1 0 0 0 0 25 32 2 0 0 0 0 26 33 2 0 0 0 0 26 37 1 0 0 0 0 27 29 1 0 0 0 0 28 34 1 1 0 0 0 29 38 1 6 0 0 0 30 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.24
Volume:	533.884
LogP:	4.187
LogD:	2.949
LogS:	-4.675
# Rotatable Bonds:	7
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	4.97
Fsp3:	0.567
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.976
MDCK Permeability:	2.8314520022831857e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.195
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.643

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.919
Plasma Protein Binding (PPB):	89.23267364501953%
Volume Distribution (VD):	2.02
Pgp-substrate:	11.080376625061035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.271
CYP2C19-inhibitor:	0.728
CYP2C19-substrate:	0.657
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.148
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.761

ADMET: Excretion

Clearance (CL):	3.637
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.755
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.083
Carcinogencity:	0.679
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC159692

Natural Product ID:	NPC159692
*Common Name:**	VZTYCOZKQWHNRH-NVAWVSNDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VZTYCOZKQWHNRH-NVAWVSNDSA-N
Standard InCHI:	InChI=1S/C30H36O8/c1-16-11-23-28(34,25(16)32)14-19(15-37-26(33)20-7-9-21(36-6)10-8-20)12-22-24-27(4,5)29(24,38-18(3)31)13-17(2)30(22,23)35/h7-12,17,22-24,34-35H,13-15H2,1-6H3/t17-,22+,23-,24-,28-,29+,30-/m1/s1
SMILES:	CC1=C[C@@H]2[C@](CC(=C[C@H]3[C@@H]4C(C)(C)[C@@]4(C[C@@H](C)[C@]23O)OC(=O)C)COC(=O)c2ccc(cc2)OC)(C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451125
PubChem CID:	24812994
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids [CHEMONTID:0002906] Phorbol esters

*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
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	8.5	ug.mL-1	PMID[536873]

☑ 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 NPC159692 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	352
0.1-0.2	1352
0.2-0.3	2689
0.3-0.4	5906
0.4-0.5	10545
0.5-0.6	7169
0.6-0.7	8961
0.7-0.8	5652
0.8-0.85	57
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC183540
0.8645	High Similarity	NPC138641
0.8645	High Similarity	NPC469647
0.8645	High Similarity	NPC283875
0.8645	High Similarity	NPC469648
0.8645	High Similarity	NPC22571
0.8543	High Similarity	NPC51181
0.8526	High Similarity	NPC145649
0.8526	High Similarity	NPC233581
0.8516	High Similarity	NPC125033
0.8481	Intermediate Similarity	NPC11410
0.8466	Intermediate Similarity	NPC161151
0.8462	Intermediate Similarity	NPC472398
0.8452	Intermediate Similarity	NPC286038
0.8397	Intermediate Similarity	NPC66991
0.8375	Intermediate Similarity	NPC41880
0.8353	Intermediate Similarity	NPC254588
0.8323	Intermediate Similarity	NPC195954
0.8323	Intermediate Similarity	NPC169942
0.8304	Intermediate Similarity	NPC102367
0.8302	Intermediate Similarity	NPC246164
0.8302	Intermediate Similarity	NPC48671
0.8291	Intermediate Similarity	NPC212257
0.8269	Intermediate Similarity	NPC132652
0.8246	Intermediate Similarity	NPC93685
0.8246	Intermediate Similarity	NPC108191
0.8239	Intermediate Similarity	NPC119252
0.8239	Intermediate Similarity	NPC140133
0.821	Intermediate Similarity	NPC88007
0.8187	Intermediate Similarity	NPC251139
0.8176	Intermediate Similarity	NPC35160
0.8176	Intermediate Similarity	NPC87630
0.8176	Intermediate Similarity	NPC116292
0.8176	Intermediate Similarity	NPC179128
0.8176	Intermediate Similarity	NPC162569
0.8176	Intermediate Similarity	NPC267469
0.8171	Intermediate Similarity	NPC68848
0.815	Intermediate Similarity	NPC186746
0.8148	Intermediate Similarity	NPC104736
0.8129	Intermediate Similarity	NPC121158
0.8125	Intermediate Similarity	NPC231668
0.8117	Intermediate Similarity	NPC475012
0.8113	Intermediate Similarity	NPC211625
0.811	Intermediate Similarity	NPC68619
0.8105	Intermediate Similarity	NPC170718
0.8098	Intermediate Similarity	NPC304692
0.8098	Intermediate Similarity	NPC194499
0.8084	Intermediate Similarity	NPC478179
0.8065	Intermediate Similarity	NPC140021
0.8063	Intermediate Similarity	NPC228842
0.8063	Intermediate Similarity	NPC156189
0.8061	Intermediate Similarity	NPC188649
0.8049	Intermediate Similarity	NPC474611
0.8049	Intermediate Similarity	NPC268602
0.8038	Intermediate Similarity	NPC208293
0.8036	Intermediate Similarity	NPC291742
0.8025	Intermediate Similarity	NPC127857
0.8025	Intermediate Similarity	NPC251865
0.8025	Intermediate Similarity	NPC114880
0.8024	Intermediate Similarity	NPC120012
0.8013	Intermediate Similarity	NPC263337
0.8013	Intermediate Similarity	NPC95449
0.8012	Intermediate Similarity	NPC195972
0.8012	Intermediate Similarity	NPC475039
0.8012	Intermediate Similarity	NPC88841
0.8012	Intermediate Similarity	NPC261659
0.8012	Intermediate Similarity	NPC285567
0.8012	Intermediate Similarity	NPC663
0.8012	Intermediate Similarity	NPC14499
0.8012	Intermediate Similarity	NPC316457
0.8012	Intermediate Similarity	NPC288602
0.8012	Intermediate Similarity	NPC476035
0.8012	Intermediate Similarity	NPC224394
0.8	Intermediate Similarity	NPC101043
0.8	Intermediate Similarity	NPC472299
0.8	Intermediate Similarity	NPC472654
0.8	Intermediate Similarity	NPC8389
0.8	Intermediate Similarity	NPC51602
0.8	Intermediate Similarity	NPC472803
0.8	Intermediate Similarity	NPC279442
0.8	Intermediate Similarity	NPC471103
0.8	Intermediate Similarity	NPC306799
0.8	Intermediate Similarity	NPC470789
0.8	Intermediate Similarity	NPC473719
0.7988	Intermediate Similarity	NPC249021
0.7988	Intermediate Similarity	NPC7059
0.7987	Intermediate Similarity	NPC255414
0.7976	Intermediate Similarity	NPC270312
0.7976	Intermediate Similarity	NPC473753
0.7976	Intermediate Similarity	NPC473766
0.7976	Intermediate Similarity	NPC476853
0.7975	Intermediate Similarity	NPC471305
0.7975	Intermediate Similarity	NPC75310
0.7975	Intermediate Similarity	NPC62051
0.7975	Intermediate Similarity	NPC471451
0.7964	Intermediate Similarity	NPC476856
0.7964	Intermediate Similarity	NPC476858
0.7964	Intermediate Similarity	NPC476860
0.7964	Intermediate Similarity	NPC476857
0.7964	Intermediate Similarity	NPC475106
0.7964	Intermediate Similarity	NPC261184
0.7963	Intermediate Similarity	NPC124842
0.7963	Intermediate Similarity	NPC294511
0.7963	Intermediate Similarity	NPC121615
0.7963	Intermediate Similarity	NPC221249
0.7962	Intermediate Similarity	NPC243577
0.7953	Intermediate Similarity	NPC148185
0.7952	Intermediate Similarity	NPC96443
0.7952	Intermediate Similarity	NPC290400
0.7952	Intermediate Similarity	NPC79571
0.795	Intermediate Similarity	NPC474305
0.795	Intermediate Similarity	NPC146014
0.7949	Intermediate Similarity	NPC475063
0.7949	Intermediate Similarity	NPC475044
0.7947	Intermediate Similarity	NPC125153
0.7941	Intermediate Similarity	NPC202428
0.7941	Intermediate Similarity	NPC266545
0.7939	Intermediate Similarity	NPC123153
0.7939	Intermediate Similarity	NPC158542
0.7939	Intermediate Similarity	NPC84349
0.7937	Intermediate Similarity	NPC93666
0.7937	Intermediate Similarity	NPC325032
0.7937	Intermediate Similarity	NPC477483
0.7937	Intermediate Similarity	NPC19747
0.7933	Intermediate Similarity	NPC194979
0.7929	Intermediate Similarity	NPC296558
0.7929	Intermediate Similarity	NPC200726
0.7927	Intermediate Similarity	NPC99381
0.7927	Intermediate Similarity	NPC472807
0.7925	Intermediate Similarity	NPC328623
0.7922	Intermediate Similarity	NPC471670
0.7922	Intermediate Similarity	NPC71638
0.7922	Intermediate Similarity	NPC64230
0.7917	Intermediate Similarity	NPC121995
0.7917	Intermediate Similarity	NPC475779
0.7917	Intermediate Similarity	NPC23387
0.7917	Intermediate Similarity	NPC478178
0.7917	Intermediate Similarity	NPC100420
0.7917	Intermediate Similarity	NPC308156
0.7914	Intermediate Similarity	NPC70344
0.7911	Intermediate Similarity	NPC471100
0.7911	Intermediate Similarity	NPC471107
0.7908	Intermediate Similarity	NPC311339
0.7907	Intermediate Similarity	NPC167340
0.7904	Intermediate Similarity	NPC477627
0.7904	Intermediate Similarity	NPC234660
0.7904	Intermediate Similarity	NPC51568
0.7904	Intermediate Similarity	NPC283209
0.7901	Intermediate Similarity	NPC272590
0.7898	Intermediate Similarity	NPC477894
0.7895	Intermediate Similarity	NPC193698
0.7892	Intermediate Similarity	NPC477188
0.7892	Intermediate Similarity	NPC239118
0.7892	Intermediate Similarity	NPC25255
0.7892	Intermediate Similarity	NPC43304
0.7892	Intermediate Similarity	NPC287559
0.7892	Intermediate Similarity	NPC472653
0.7892	Intermediate Similarity	NPC477190
0.7888	Intermediate Similarity	NPC125182
0.7888	Intermediate Similarity	NPC146388
0.7888	Intermediate Similarity	NPC470790
0.7888	Intermediate Similarity	NPC475848
0.7888	Intermediate Similarity	NPC474306
0.7888	Intermediate Similarity	NPC253591
0.7888	Intermediate Similarity	NPC470791
0.7888	Intermediate Similarity	NPC17600
0.7888	Intermediate Similarity	NPC69647
0.7885	Intermediate Similarity	NPC475045
0.7885	Intermediate Similarity	NPC67003
0.7882	Intermediate Similarity	NPC177362
0.7882	Intermediate Similarity	NPC302392
0.7882	Intermediate Similarity	NPC118086
0.7882	Intermediate Similarity	NPC473094
0.7879	Intermediate Similarity	NPC474360
0.7879	Intermediate Similarity	NPC472772
0.7879	Intermediate Similarity	NPC471968
0.7879	Intermediate Similarity	NPC81405
0.7875	Intermediate Similarity	NPC250046
0.7875	Intermediate Similarity	NPC60509
0.7875	Intermediate Similarity	NPC81698
0.7875	Intermediate Similarity	NPC71821
0.7875	Intermediate Similarity	NPC216755
0.7875	Intermediate Similarity	NPC471174
0.7871	Intermediate Similarity	NPC156888
0.7871	Intermediate Similarity	NPC470721
0.7871	Intermediate Similarity	NPC276652
0.7871	Intermediate Similarity	NPC6100
0.7871	Intermediate Similarity	NPC470722
0.7871	Intermediate Similarity	NPC119542
0.787	Intermediate Similarity	NPC472774
0.787	Intermediate Similarity	NPC314653
0.787	Intermediate Similarity	NPC472775
0.787	Intermediate Similarity	NPC476861
0.787	Intermediate Similarity	NPC316262
0.787	Intermediate Similarity	NPC476850
0.7867	Intermediate Similarity	NPC2596
0.7866	Intermediate Similarity	NPC477669
0.7862	Intermediate Similarity	NPC274085
0.7862	Intermediate Similarity	NPC475552
0.7862	Intermediate Similarity	NPC89664

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 NPC159692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	901
0.2-0.3	1554
0.3-0.4	2534
0.4-0.5	2131
0.5-0.6	1166
0.6-0.7	484
0.7-0.8	86
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
0.8246	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4628	Phase 3
0.7886	Intermediate Similarity	NPD8434	Phase 2
0.7866	Intermediate Similarity	NPD7819	Suspended
0.7799	Intermediate Similarity	NPD7236	Approved
0.7791	Intermediate Similarity	NPD6599	Discontinued
0.7722	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7669	Intermediate Similarity	NPD7239	Suspended
0.7654	Intermediate Similarity	NPD6273	Approved
0.7651	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7458	Discontinued
0.7619	Intermediate Similarity	NPD7075	Discontinued
0.7593	Intermediate Similarity	NPD2534	Approved
0.7593	Intermediate Similarity	NPD2533	Approved
0.7593	Intermediate Similarity	NPD2532	Approved
0.7545	Intermediate Similarity	NPD5761	Phase 2
0.7545	Intermediate Similarity	NPD5760	Phase 2
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.7531	Intermediate Similarity	NPD6799	Approved
0.7515	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD6764	Approved
0.75	Intermediate Similarity	NPD6765	Approved
0.7485	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7467	Intermediate Similarity	NPD3972	Approved
0.7453	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7003	Approved
0.7438	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7411	Suspended
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3764	Approved
0.7418	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7396	Intermediate Similarity	NPD3817	Phase 2
0.7389	Intermediate Similarity	NPD6355	Discontinued
0.7381	Intermediate Similarity	NPD6801	Discontinued
0.7378	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2346	Discontinued
0.7375	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1608	Approved
0.7346	Intermediate Similarity	NPD3750	Approved
0.7341	Intermediate Similarity	NPD6232	Discontinued
0.7333	Intermediate Similarity	NPD6784	Approved
0.7333	Intermediate Similarity	NPD6785	Approved
0.733	Intermediate Similarity	NPD5844	Phase 1
0.7312	Intermediate Similarity	NPD6100	Approved
0.7312	Intermediate Similarity	NPD6099	Approved
0.7294	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7799	Discontinued
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD5763	Approved
0.7262	Intermediate Similarity	NPD4380	Phase 2
0.7261	Intermediate Similarity	NPD8032	Phase 2
0.7255	Intermediate Similarity	NPD1876	Approved
0.7255	Intermediate Similarity	NPD1283	Approved
0.7251	Intermediate Similarity	NPD7057	Phase 3
0.7251	Intermediate Similarity	NPD7058	Phase 2
0.7251	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3882	Suspended
0.725	Intermediate Similarity	NPD1510	Phase 2
0.725	Intermediate Similarity	NPD3748	Approved
0.7248	Intermediate Similarity	NPD9545	Approved
0.7247	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1607	Approved
0.7225	Intermediate Similarity	NPD5494	Approved
0.7215	Intermediate Similarity	NPD1240	Approved
0.7215	Intermediate Similarity	NPD2979	Phase 3
0.7211	Intermediate Similarity	NPD7497	Discontinued
0.7209	Intermediate Similarity	NPD3749	Approved
0.7205	Intermediate Similarity	NPD2796	Approved
0.7198	Intermediate Similarity	NPD8150	Discontinued
0.7197	Intermediate Similarity	NPD2313	Discontinued
0.7195	Intermediate Similarity	NPD6190	Approved
0.7193	Intermediate Similarity	NPD5402	Approved
0.7186	Intermediate Similarity	NPD920	Approved
0.7186	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6832	Phase 2
0.7178	Intermediate Similarity	NPD2800	Approved
0.7176	Intermediate Similarity	NPD37	Approved
0.7169	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7159	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD17	Approved
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4966	Approved
0.7151	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7135	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7095	Approved
0.7134	Intermediate Similarity	NPD8166	Discontinued
0.7125	Intermediate Similarity	NPD6651	Approved
0.712	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1549	Phase 2
0.7108	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4140	Approved
0.7102	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2438	Suspended
0.7091	Intermediate Similarity	NPD3887	Approved
0.7091	Intermediate Similarity	NPD2354	Approved
0.7089	Intermediate Similarity	NPD3268	Approved
0.7086	Intermediate Similarity	NPD5585	Approved
0.7086	Intermediate Similarity	NPD6959	Discontinued
0.7069	Intermediate Similarity	NPD6234	Discontinued
0.7066	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD230	Phase 1
0.7059	Intermediate Similarity	NPD7028	Phase 2
0.7059	Intermediate Similarity	NPD1281	Approved
0.7055	Intermediate Similarity	NPD2344	Approved
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD1552	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
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2798	Approved
0.7045	Intermediate Similarity	NPD5710	Approved
0.7045	Intermediate Similarity	NPD5711	Approved
0.7044	Intermediate Similarity	NPD6233	Phase 2
0.7044	Intermediate Similarity	NPD6663	Approved
0.7039	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1778	Approved
0.7037	Intermediate Similarity	NPD4308	Phase 3
0.7037	Intermediate Similarity	NPD7033	Discontinued
0.7035	Intermediate Similarity	NPD2801	Approved
0.7033	Intermediate Similarity	NPD8312	Approved
0.7033	Intermediate Similarity	NPD8313	Approved
0.7031	Intermediate Similarity	NPD7435	Discontinued
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4110	Phase 3
0.7024	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6385	Approved
0.7018	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6386	Approved
0.7017	Intermediate Similarity	NPD8368	Discontinued
0.7011	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5736	Approved
0.7	Intermediate Similarity	NPD4060	Phase 1
0.6995	Remote Similarity	NPD8407	Phase 2
0.6994	Remote Similarity	NPD1551	Phase 2
0.6994	Remote Similarity	NPD4477	Approved
0.6994	Remote Similarity	NPD4476	Approved
0.6989	Remote Similarity	NPD7199	Phase 2
0.6987	Remote Similarity	NPD2797	Approved
0.6983	Remote Similarity	NPD3818	Discontinued
0.6983	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5403	Approved
0.6981	Remote Similarity	NPD6798	Discontinued
0.6978	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1934	Approved
0.6975	Remote Similarity	NPD7097	Phase 1
0.6974	Remote Similarity	NPD5691	Approved
0.6971	Remote Similarity	NPD919	Approved
0.697	Remote Similarity	NPD1243	Approved
0.6966	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6166	Phase 2
0.6966	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5401	Approved
0.6961	Remote Similarity	NPD5953	Discontinued
0.6951	Remote Similarity	NPD2353	Approved
0.6951	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7286	Phase 2
0.6943	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7961	Discontinued
0.6936	Remote Similarity	NPD1465	Phase 2
0.6928	Remote Similarity	NPD4626	Approved
0.6928	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1512	Approved
0.6923	Remote Similarity	NPD5049	Phase 3
0.6923	Remote Similarity	NPD6559	Discontinued
0.6919	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3926	Phase 2
0.6894	Remote Similarity	NPD4307	Phase 2
0.6893	Remote Similarity	NPD1247	Approved
0.689	Remote Similarity	NPD2531	Phase 2
0.6889	Remote Similarity	NPD7177	Discontinued
0.6889	Remote Similarity	NPD3751	Discontinued
0.6889	Remote Similarity	NPD7228	Approved
0.6886	Remote Similarity	NPD2309	Approved
0.6883	Remote Similarity	NPD3496	Discontinued
0.6879	Remote Similarity	NPD3266	Approved
0.6879	Remote Similarity	NPD3267	Approved
0.6875	Remote Similarity	NPD6778	Approved
0.6875	Remote Similarity	NPD6781	Approved
0.6875	Remote Similarity	NPD6776	Approved
0.6875	Remote Similarity	NPD6779	Approved
0.6875	Remote Similarity	NPD6782	Approved
0.6875	Remote Similarity	NPD6780	Approved
0.6875	Remote Similarity	NPD6777	Approved
0.6875	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD8404	Phase 2
0.6863	Remote Similarity	NPD1651	Approved
0.6859	Remote Similarity	NPD4359	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