NPASS Compound

Structure

NPC310586 OpenBabel07101718242D 41 45 0 0 1 0 0 0 0 0999 V2000 4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9847 4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -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 0.8660 1.5000 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 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2500 5.8564 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 3.9192 5.1132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6102 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9921 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7709 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6757 3.5385 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6320 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3230 3.0032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 3.5591 6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7709 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3024 3.3305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9629 4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3448 2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 2 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 31 1 0 0 0 0 9 10 1 0 0 0 0 9 24 1 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 33 1 0 0 0 0 13 14 1 0 0 0 0 13 31 1 0 0 0 0 15 26 1 0 0 0 0 15 32 1 0 0 0 0 16 18 1 0 0 0 0 16 35 1 0 0 0 0 17 33 1 0 0 0 0 17 34 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 29 1 0 0 0 0 20 3 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 4 1 1 0 0 0 21 28 1 0 0 0 0 21 30 1 0 0 0 0 22 36 2 0 0 0 0 22 40 1 0 0 0 0 23 37 2 0 0 0 0 23 41 1 0 0 0 0 24 33 1 1 0 0 0 25 38 2 0 0 0 0 26 28 1 0 0 0 0 26 40 1 1 0 0 0 27 32 1 6 0 0 0 27 34 1 0 0 0 0 28 31 1 1 0 0 0 29 39 2 0 0 0 0 30 29 1 1 0 0 0 30 41 1 0 0 0 0 31 32 1 1 0 0 0 32 8 1 6 0 0 0 33 34 1 6 0 0 0 34 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.36
Volume:	602.187
LogP:	3.75
LogD:	2.979
LogS:	-4.46
# Rotatable Bonds:	10
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.305
Synthetic Accessibility Score:	6.16
Fsp3:	0.824
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.154
MDCK Permeability:	1.3345291336008813e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	86.97512817382812%
Volume Distribution (VD):	0.774
Pgp-substrate:	9.509241104125977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.746
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.636

ADMET: Excretion

Clearance (CL):	3.821
Half-life (T1/2):	0.567

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.788
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.539
Carcinogencity:	0.712
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC310586

Natural Product ID:	NPC310586
*Common Name:**	DVYXBXNSRWHEAH-QDNFKKIJSA-N
IUPAC Name:	n.a.
Synonyms:	1,2-Dihydroneoboutomellerone
Standard InCHIKey:	DVYXBXNSRWHEAH-QDNFKKIJSA-N
Standard InCHI:	InChI=1S/C34H50O7/c1-18(16-35)19(2)29(39)30(41-23(6)37)21(4)28-26(40-22(5)36)15-32(8)27-10-9-24-20(3)25(38)11-12-33(24)17-34(27,33)14-13-31(28,32)7/h18,20-21,24,26-28,30,35H,2,9-17H2,1,3-8H3/t18-,20-,21-,24-,26-,27-,28-,30+,31+,32-,33+,34-/m0/s1
SMILES:	OC[C@@H](C(=C)C(=O)[C@@H]([C@H]([C@H]1[C@@H](OC(=O)C)C[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CCC(=O)[C@H]2C)C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1941153
PubChem CID:	57331837
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22168134]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22206869]
NPO16384	Neoboutonia melleri	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	2
Others	6

Activity Type	# Activity
Others	8

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	48.0	n.a.	PMID[461122]
NPT2	Others	Unspecified	FC	=	45.0	n.a.	PMID[461122]
NPT2	Others	Unspecified	FC	=	0.9	n.a.	PMID[461122]
NPT2	Others	Unspecified	IC50	=	13000.0	nM	PMID[461122]
NPT2	Others	Unspecified	IC50	=	17000.0	nM	PMID[461122]
NPT2	Others	Unspecified	FC	=	48.0	n.a.	PMID[461123]
NPT2	Others	Unspecified	FC	=	45.0	n.a.	PMID[461123]
NPT2	Others	Unspecified	FC	=	0.9	n.a.	PMID[461123]

☑ 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 NPC310586 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	248
0.1-0.2	1824
0.2-0.3	6637
0.3-0.4	13425
0.4-0.5	6965
0.5-0.6	6204
0.6-0.7	5799
0.7-0.8	1463
0.8-0.85	111
0.85-0.9	13
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC15396
0.9412	High Similarity	NPC470281
0.9307	High Similarity	NPC211224
0.9223	High Similarity	NPC118860
0.9223	High Similarity	NPC231589
0.9223	High Similarity	NPC214797
0.9135	High Similarity	NPC170487
0.9048	High Similarity	NPC202889
0.9029	High Similarity	NPC241927
0.9029	High Similarity	NPC258543
0.8922	High Similarity	NPC265127
0.8879	High Similarity	NPC270958
0.8774	High Similarity	NPC71348
0.875	High Similarity	NPC470269
0.8738	High Similarity	NPC181265
0.8725	High Similarity	NPC470310
0.8716	High Similarity	NPC118638
0.8687	High Similarity	NPC29410
0.8687	High Similarity	NPC200054
0.8641	High Similarity	NPC235889
0.8586	High Similarity	NPC98639
0.8571	High Similarity	NPC94529
0.8558	High Similarity	NPC50535
0.8544	High Similarity	NPC87927
0.8544	High Similarity	NPC469985
0.8544	High Similarity	NPC221421
0.8529	High Similarity	NPC163963
0.8529	High Similarity	NPC289148
0.8529	High Similarity	NPC52899
0.8515	High Similarity	NPC162459
0.8515	High Similarity	NPC20479
0.8515	High Similarity	NPC38296
0.8515	High Similarity	NPC471038
0.8515	High Similarity	NPC38471
0.8515	High Similarity	NPC28864
0.8515	High Similarity	NPC98837
0.8476	Intermediate Similarity	NPC176949
0.8476	Intermediate Similarity	NPC86852
0.8476	Intermediate Similarity	NPC201908
0.8476	Intermediate Similarity	NPC251824
0.8462	Intermediate Similarity	NPC47281
0.8462	Intermediate Similarity	NPC29705
0.8447	Intermediate Similarity	NPC286519
0.8447	Intermediate Similarity	NPC214946
0.8447	Intermediate Similarity	NPC304832
0.8447	Intermediate Similarity	NPC88203
0.8447	Intermediate Similarity	NPC271266
0.8447	Intermediate Similarity	NPC308351
0.8447	Intermediate Similarity	NPC246736
0.8447	Intermediate Similarity	NPC76866
0.8447	Intermediate Similarity	NPC148628
0.8431	Intermediate Similarity	NPC293866
0.8431	Intermediate Similarity	NPC287676
0.8381	Intermediate Similarity	NPC278628
0.8381	Intermediate Similarity	NPC196528
0.8381	Intermediate Similarity	NPC231530
0.8381	Intermediate Similarity	NPC28791
0.835	Intermediate Similarity	NPC252614
0.835	Intermediate Similarity	NPC46848
0.835	Intermediate Similarity	NPC253886
0.835	Intermediate Similarity	NPC121218
0.8333	Intermediate Similarity	NPC89099
0.8333	Intermediate Similarity	NPC78427
0.8333	Intermediate Similarity	NPC16911
0.8318	Intermediate Similarity	NPC304495
0.8317	Intermediate Similarity	NPC42042
0.8317	Intermediate Similarity	NPC329910
0.8317	Intermediate Similarity	NPC219353
0.8286	Intermediate Similarity	NPC98603
0.8269	Intermediate Similarity	NPC275990
0.8269	Intermediate Similarity	NPC170615
0.8252	Intermediate Similarity	NPC218383
0.8252	Intermediate Similarity	NPC94906
0.8241	Intermediate Similarity	NPC197428
0.8235	Intermediate Similarity	NPC10864
0.8224	Intermediate Similarity	NPC231278
0.8224	Intermediate Similarity	NPC218123
0.8224	Intermediate Similarity	NPC112895
0.8218	Intermediate Similarity	NPC470229
0.8218	Intermediate Similarity	NPC470232
0.8208	Intermediate Similarity	NPC37600
0.8208	Intermediate Similarity	NPC470267
0.8208	Intermediate Similarity	NPC475571
0.8208	Intermediate Similarity	NPC474101
0.82	Intermediate Similarity	NPC294263
0.819	Intermediate Similarity	NPC140723
0.819	Intermediate Similarity	NPC216114
0.819	Intermediate Similarity	NPC277074
0.819	Intermediate Similarity	NPC209298
0.819	Intermediate Similarity	NPC122811
0.8173	Intermediate Similarity	NPC75941
0.8155	Intermediate Similarity	NPC474793
0.8155	Intermediate Similarity	NPC472028
0.8137	Intermediate Similarity	NPC13949
0.8137	Intermediate Similarity	NPC234564
0.8119	Intermediate Similarity	NPC475118
0.8119	Intermediate Similarity	NPC47853
0.8119	Intermediate Similarity	NPC470385
0.8119	Intermediate Similarity	NPC470386
0.8113	Intermediate Similarity	NPC84928
0.8113	Intermediate Similarity	NPC96268
0.8113	Intermediate Similarity	NPC301787
0.81	Intermediate Similarity	NPC250753
0.8095	Intermediate Similarity	NPC124544
0.8091	Intermediate Similarity	NPC280782
0.8077	Intermediate Similarity	NPC470388
0.8077	Intermediate Similarity	NPC267921
0.8077	Intermediate Similarity	NPC293890
0.8056	Intermediate Similarity	NPC273155
0.8039	Intermediate Similarity	NPC210214
0.8039	Intermediate Similarity	NPC469599
0.8037	Intermediate Similarity	NPC295366
0.8037	Intermediate Similarity	NPC222833
0.8037	Intermediate Similarity	NPC138908
0.8037	Intermediate Similarity	NPC470309
0.8037	Intermediate Similarity	NPC200957
0.8036	Intermediate Similarity	NPC148458
0.8021	Intermediate Similarity	NPC245866
0.802	Intermediate Similarity	NPC224060
0.802	Intermediate Similarity	NPC206810
0.802	Intermediate Similarity	NPC244356
0.8019	Intermediate Similarity	NPC159442
0.8019	Intermediate Similarity	NPC139347
0.8	Intermediate Similarity	NPC236585
0.8	Intermediate Similarity	NPC71706
0.8	Intermediate Similarity	NPC471790
0.8	Intermediate Similarity	NPC295276
0.8	Intermediate Similarity	NPC43775
0.8	Intermediate Similarity	NPC329953
0.7981	Intermediate Similarity	NPC26270
0.7965	Intermediate Similarity	NPC239273
0.7963	Intermediate Similarity	NPC44063
0.7963	Intermediate Similarity	NPC166993
0.7961	Intermediate Similarity	NPC104568
0.7961	Intermediate Similarity	NPC470387
0.7959	Intermediate Similarity	NPC471042
0.7959	Intermediate Similarity	NPC70661
0.7946	Intermediate Similarity	NPC300051
0.7944	Intermediate Similarity	NPC13149
0.7944	Intermediate Similarity	NPC137657
0.7944	Intermediate Similarity	NPC474558
0.7944	Intermediate Similarity	NPC202793
0.7941	Intermediate Similarity	NPC191094
0.7941	Intermediate Similarity	NPC272635
0.7941	Intermediate Similarity	NPC169751
0.7941	Intermediate Similarity	NPC470423
0.7941	Intermediate Similarity	NPC302008
0.7928	Intermediate Similarity	NPC100267
0.7928	Intermediate Similarity	NPC475524
0.7925	Intermediate Similarity	NPC309388
0.7925	Intermediate Similarity	NPC475803
0.7921	Intermediate Similarity	NPC154101
0.7921	Intermediate Similarity	NPC52756
0.7921	Intermediate Similarity	NPC211403
0.7921	Intermediate Similarity	NPC198054
0.7921	Intermediate Similarity	NPC476168
0.7921	Intermediate Similarity	NPC470230
0.7921	Intermediate Similarity	NPC198242
0.7909	Intermediate Similarity	NPC471093
0.7905	Intermediate Similarity	NPC37047
0.7905	Intermediate Similarity	NPC108371
0.7905	Intermediate Similarity	NPC180733
0.7905	Intermediate Similarity	NPC41971
0.7905	Intermediate Similarity	NPC15390
0.7885	Intermediate Similarity	NPC87090
0.7879	Intermediate Similarity	NPC134197
0.7879	Intermediate Similarity	NPC153604
0.7876	Intermediate Similarity	NPC298278
0.787	Intermediate Similarity	NPC96377
0.787	Intermediate Similarity	NPC4115
0.7864	Intermediate Similarity	NPC84018
0.7864	Intermediate Similarity	NPC263135
0.7864	Intermediate Similarity	NPC231060
0.7864	Intermediate Similarity	NPC138245
0.7864	Intermediate Similarity	NPC288906
0.7857	Intermediate Similarity	NPC52634
0.7857	Intermediate Similarity	NPC472926
0.7857	Intermediate Similarity	NPC471252
0.785	Intermediate Similarity	NPC96217
0.785	Intermediate Similarity	NPC266
0.7843	Intermediate Similarity	NPC181594
0.7843	Intermediate Similarity	NPC144739
0.7838	Intermediate Similarity	NPC94650
0.7838	Intermediate Similarity	NPC29505
0.783	Intermediate Similarity	NPC148279
0.783	Intermediate Similarity	NPC474327
0.783	Intermediate Similarity	NPC477356
0.783	Intermediate Similarity	NPC39683
0.7822	Intermediate Similarity	NPC80401
0.7822	Intermediate Similarity	NPC100313
0.7822	Intermediate Similarity	NPC77756
0.7818	Intermediate Similarity	NPC2766
0.781	Intermediate Similarity	NPC271387
0.781	Intermediate Similarity	NPC153792
0.7807	Intermediate Similarity	NPC472927
0.78	Intermediate Similarity	NPC56413
0.7798	Intermediate Similarity	NPC475294
0.7798	Intermediate Similarity	NPC186054
0.7788	Intermediate Similarity	NPC256227
0.7788	Intermediate Similarity	NPC49371

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 NPC310586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	2196
0.2-0.3	4081
0.3-0.4	1739
0.4-0.5	426
0.5-0.6	212
0.6-0.7	157
0.7-0.8	99
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
0.8056	Intermediate Similarity	NPD6881	Approved
0.8056	Intermediate Similarity	NPD6899	Approved
0.8037	Intermediate Similarity	NPD7128	Approved
0.8037	Intermediate Similarity	NPD5739	Approved
0.8037	Intermediate Similarity	NPD6675	Approved
0.8037	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6649	Approved
0.8	Intermediate Similarity	NPD6650	Approved
0.7982	Intermediate Similarity	NPD6372	Approved
0.7982	Intermediate Similarity	NPD6373	Approved
0.7963	Intermediate Similarity	NPD5697	Approved
0.7928	Intermediate Similarity	NPD8297	Approved
0.7909	Intermediate Similarity	NPD6883	Approved
0.7909	Intermediate Similarity	NPD7290	Approved
0.7909	Intermediate Similarity	NPD7102	Approved
0.789	Intermediate Similarity	NPD6011	Approved
0.789	Intermediate Similarity	NPD7320	Approved
0.7885	Intermediate Similarity	NPD6084	Phase 2
0.7885	Intermediate Similarity	NPD6083	Phase 2
0.7863	Intermediate Similarity	NPD7604	Phase 2
0.7838	Intermediate Similarity	NPD6869	Approved
0.7838	Intermediate Similarity	NPD6617	Approved
0.7838	Intermediate Similarity	NPD6847	Approved
0.7818	Intermediate Similarity	NPD6012	Approved
0.7818	Intermediate Similarity	NPD6014	Approved
0.7818	Intermediate Similarity	NPD6013	Approved
0.7798	Intermediate Similarity	NPD5701	Approved
0.7768	Intermediate Similarity	NPD6882	Approved
0.7745	Intermediate Similarity	NPD8034	Phase 2
0.7745	Intermediate Similarity	NPD8035	Phase 2
0.7706	Intermediate Similarity	NPD6008	Approved
0.7699	Intermediate Similarity	NPD4632	Approved
0.7679	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6399	Phase 3
0.7653	Intermediate Similarity	NPD4788	Approved
0.7652	Intermediate Similarity	NPD6009	Approved
0.7642	Intermediate Similarity	NPD5696	Approved
0.7607	Intermediate Similarity	NPD6319	Approved
0.7603	Intermediate Similarity	NPD7736	Approved
0.7542	Intermediate Similarity	NPD5983	Phase 2
0.7524	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD7492	Approved
0.7458	Intermediate Similarity	NPD6054	Approved
0.7451	Intermediate Similarity	NPD5737	Approved
0.7451	Intermediate Similarity	NPD6672	Approved
0.7438	Intermediate Similarity	NPD6336	Discontinued
0.7438	Intermediate Similarity	NPD6616	Approved
0.7436	Intermediate Similarity	NPD6335	Approved
0.7414	Intermediate Similarity	NPD6274	Approved
0.7407	Intermediate Similarity	NPD5286	Approved
0.7407	Intermediate Similarity	NPD4696	Approved
0.7407	Intermediate Similarity	NPD5285	Approved
0.7383	Intermediate Similarity	NPD4755	Approved
0.7379	Intermediate Similarity	NPD6673	Approved
0.7379	Intermediate Similarity	NPD6904	Approved
0.7379	Intermediate Similarity	NPD6080	Approved
0.7377	Intermediate Similarity	NPD7078	Approved
0.7377	Intermediate Similarity	NPD8293	Discontinued
0.7373	Intermediate Similarity	NPD7101	Approved
0.7373	Intermediate Similarity	NPD7100	Approved
0.735	Intermediate Similarity	NPD6317	Approved
0.7339	Intermediate Similarity	NPD5223	Approved
0.7333	Intermediate Similarity	NPD6370	Approved
0.7327	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7638	Approved
0.7311	Intermediate Similarity	NPD6059	Approved
0.7288	Intermediate Similarity	NPD6314	Approved
0.7288	Intermediate Similarity	NPD6313	Approved
0.7282	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7255	Intermediate Similarity	NPD6409	Approved
0.7255	Intermediate Similarity	NPD6684	Approved
0.7255	Intermediate Similarity	NPD5330	Approved
0.7255	Intermediate Similarity	NPD7146	Approved
0.7255	Intermediate Similarity	NPD6098	Approved
0.7255	Intermediate Similarity	NPD7334	Approved
0.7255	Intermediate Similarity	NPD7521	Approved
0.725	Intermediate Similarity	NPD6015	Approved
0.725	Intermediate Similarity	NPD6016	Approved
0.7248	Intermediate Similarity	NPD7640	Approved
0.7248	Intermediate Similarity	NPD7639	Approved
0.7248	Intermediate Similarity	NPD4700	Approved
0.7212	Intermediate Similarity	NPD4753	Phase 2
0.7207	Intermediate Similarity	NPD5174	Approved
0.7207	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4629	Approved
0.7196	Intermediate Similarity	NPD5210	Approved
0.719	Intermediate Similarity	NPD5988	Approved
0.7168	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD5141	Approved
0.713	Intermediate Similarity	NPD4634	Approved
0.713	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5222	Approved
0.713	Intermediate Similarity	NPD4697	Phase 3
0.713	Intermediate Similarity	NPD5221	Approved
0.7119	Intermediate Similarity	NPD6868	Approved
0.7115	Intermediate Similarity	NPD6903	Approved
0.7107	Intermediate Similarity	NPD6909	Approved
0.7107	Intermediate Similarity	NPD6908	Approved
0.7107	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6050	Approved
0.7075	Intermediate Similarity	NPD6079	Approved
0.7075	Intermediate Similarity	NPD5693	Phase 1
0.7064	Intermediate Similarity	NPD7902	Approved
0.7064	Intermediate Similarity	NPD5173	Approved
0.7059	Intermediate Similarity	NPD3666	Approved
0.7059	Intermediate Similarity	NPD4786	Approved
0.7059	Intermediate Similarity	NPD3133	Approved
0.7059	Intermediate Similarity	NPD3665	Phase 1
0.7054	Intermediate Similarity	NPD4754	Approved
0.7048	Intermediate Similarity	NPD5328	Approved
0.7009	Intermediate Similarity	NPD6053	Discontinued
0.6992	Remote Similarity	NPD8328	Phase 3
0.699	Remote Similarity	NPD5329	Approved
0.6981	Remote Similarity	NPD5692	Phase 3
0.697	Remote Similarity	NPD6118	Approved
0.697	Remote Similarity	NPD6697	Approved
0.697	Remote Similarity	NPD6114	Approved
0.697	Remote Similarity	NPD6115	Approved
0.6957	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5128	Approved
0.6957	Remote Similarity	NPD4730	Approved
0.6957	Remote Similarity	NPD4729	Approved
0.6949	Remote Similarity	NPD8133	Approved
0.6944	Remote Similarity	NPD7748	Approved
0.693	Remote Similarity	NPD4768	Approved
0.693	Remote Similarity	NPD4767	Approved
0.6917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5694	Approved
0.6916	Remote Similarity	NPD5281	Approved
0.6916	Remote Similarity	NPD5284	Approved
0.6905	Remote Similarity	NPD6033	Approved
0.6893	Remote Similarity	NPD4197	Approved
0.688	Remote Similarity	NPD7507	Approved
0.6875	Remote Similarity	NPD5777	Approved
0.6869	Remote Similarity	NPD6116	Phase 1
0.6863	Remote Similarity	NPD3667	Approved
0.6852	Remote Similarity	NPD4202	Approved
0.6838	Remote Similarity	NPD5249	Phase 3
0.6838	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5251	Approved
0.6838	Remote Similarity	NPD5169	Approved
0.6838	Remote Similarity	NPD5247	Approved
0.6838	Remote Similarity	NPD5135	Approved
0.6838	Remote Similarity	NPD5250	Approved
0.6838	Remote Similarity	NPD5248	Approved
0.6837	Remote Similarity	NPD3702	Approved
0.6814	Remote Similarity	NPD7632	Discontinued
0.6789	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6001	Approved
0.6789	Remote Similarity	NPD7900	Approved
0.678	Remote Similarity	NPD5215	Approved
0.678	Remote Similarity	NPD5216	Approved
0.678	Remote Similarity	NPD5217	Approved
0.678	Remote Similarity	NPD5127	Approved
0.6777	Remote Similarity	NPD7115	Discovery
0.6771	Remote Similarity	NPD4244	Approved
0.6771	Remote Similarity	NPD4789	Approved
0.6771	Remote Similarity	NPD4245	Approved
0.6768	Remote Similarity	NPD6117	Approved
0.6762	Remote Similarity	NPD5279	Phase 3
0.6762	Remote Similarity	NPD3618	Phase 1
0.6762	Remote Similarity	NPD5690	Phase 2
0.6759	Remote Similarity	NPD7515	Phase 2
0.6757	Remote Similarity	NPD5959	Approved
0.6735	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6614	Approved
0.6719	Remote Similarity	NPD7319	Approved
0.6699	Remote Similarity	NPD4223	Phase 3
0.6699	Remote Similarity	NPD6435	Approved
0.6699	Remote Similarity	NPD4221	Approved
0.6696	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6371	Approved
0.6692	Remote Similarity	NPD6334	Approved
0.6692	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD3698	Phase 2
0.6636	Remote Similarity	NPD5208	Approved
0.6612	Remote Similarity	NPD5167	Approved
0.6604	Remote Similarity	NPD4694	Approved
0.6604	Remote Similarity	NPD5280	Approved
0.6579	Remote Similarity	NPD1700	Approved
0.6577	Remote Similarity	NPD5654	Approved
0.6574	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5956	Approved
0.6531	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6081	Approved
0.6531	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5168	Approved
0.6514	Remote Similarity	NPD5207	Approved
0.6514	Remote Similarity	NPD5785	Approved
0.6505	Remote Similarity	NPD5368	Approved
0.6505	Remote Similarity	NPD4695	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