NPASS Compound

Structure

NPC190713 OpenBabel07101719142D 35 38 0 0 1 0 0 0 0 0999 V2000 4.8747 -2.6765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 -1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 3.8660 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 0.7431 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5568 -5.2509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1805 -2.3164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6453 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9236 -2.9855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3884 -1.3383 0.0000 C 0 0 1 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7157 -3.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3395 -1.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4589 -4.6328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7647 -4.2727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 35 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 24 2 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 27 1 0 0 0 0 20 2 1 1 0 0 0 20 30 1 0 0 0 0 21 32 1 1 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 6 0 0 0 26 28 1 0 0 0 0 26 33 1 1 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 29 5 1 6 0 0 0 30 31 1 1 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.36
Volume:	535.121
LogP:	5.67
LogD:	4.416
LogS:	-4.588
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	4.998
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.137
MDCK Permeability:	2.343538471905049e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	85.40180206298828%
Volume Distribution (VD):	1.184
Pgp-substrate:	3.3193938732147217%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.428
CYP2C19-inhibitor:	0.207
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.369
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	11.485
Half-life (T1/2):	0.086

ADMET: Toxicity

hERG Blockers:	0.846
Human Hepatotoxicity (H-HT):	0.561
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.616
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.256
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC190713

Natural Product ID:	NPC190713
*Common Name:**	Garcihombronanes C
IUPAC Name:	methyl (E,4R,6R)-4-hydroxy-6-[(3R,5R,10S,13S,17S)-3-hydroxy-4,4,10,13,17-pentamethyl-2,3,5,6,7,11,12,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoate
Synonyms:	Garcihombronanes C
Standard InCHIKey:	DSRXFFLSYVPYKU-NVHZQPCMSA-N
Standard InCHI:	InChI=1S/C31H48O4/c1-19(27(34)35-8)17-21(32)18-20(2)30(6)15-12-24-22-9-10-25-28(3,4)26(33)13-14-29(25,5)23(22)11-16-31(24,30)7/h12,17,20-21,25-26,32-33H,9-11,13-16,18H2,1-8H3/b19-17+/t20-,21+,25+,26-,29-,30+,31-/m1/s1
SMILES:	COC(=O)/C(=C/[C@@H](C[C@H]([C@]1(C)CC=C2[C@@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511954
PubChem CID:	44593343
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	barks	n.a.	n.a.	PMID[15620248]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25515	Garcinia speciosa	Species	Clusiaceae	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
GI50	3
MIC	1
Others	1

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	22300.0	nM	PMID[451947]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	37900.0	nM	PMID[451947]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	38600.0	nM	PMID[451947]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	17.36	%	PMID[451947]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[451948]

☑ 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 NPC190713 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	177
0.1-0.2	959
0.2-0.3	3857
0.3-0.4	8519
0.4-0.5	14713
0.5-0.6	7568
0.6-0.7	5170
0.7-0.8	1559
0.8-0.85	136
0.85-0.9	37
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC92275
0.9444	High Similarity	NPC214697
0.9333	High Similarity	NPC212948
0.9247	High Similarity	NPC141401
0.9032	High Similarity	NPC474909
0.8947	High Similarity	NPC218107
0.8901	High Similarity	NPC472240
0.8901	High Similarity	NPC262858
0.8817	High Similarity	NPC38232
0.8723	High Similarity	NPC469406
0.8696	High Similarity	NPC146554
0.8667	High Similarity	NPC109528
0.8646	High Similarity	NPC99726
0.8646	High Similarity	NPC253826
0.8617	High Similarity	NPC476304
0.8602	High Similarity	NPC280149
0.8602	High Similarity	NPC221111
0.8586	High Similarity	NPC85742
0.8557	High Similarity	NPC57079
0.8557	High Similarity	NPC108368
0.8557	High Similarity	NPC471717
0.8526	High Similarity	NPC476186
0.8526	High Similarity	NPC279410
0.8526	High Similarity	NPC119562
0.8511	High Similarity	NPC74296
0.8511	High Similarity	NPC110923
0.85	High Similarity	NPC472868
0.8478	Intermediate Similarity	NPC475772
0.8421	Intermediate Similarity	NPC205034
0.8421	Intermediate Similarity	NPC152778
0.8421	Intermediate Similarity	NPC472871
0.8421	Intermediate Similarity	NPC162615
0.8404	Intermediate Similarity	NPC182136
0.8404	Intermediate Similarity	NPC310479
0.8404	Intermediate Similarity	NPC78973
0.84	Intermediate Similarity	NPC171014
0.8384	Intermediate Similarity	NPC118174
0.8367	Intermediate Similarity	NPC48647
0.8367	Intermediate Similarity	NPC166745
0.8367	Intermediate Similarity	NPC235464
0.8365	Intermediate Similarity	NPC284162
0.8365	Intermediate Similarity	NPC255401
0.8352	Intermediate Similarity	NPC302360
0.8351	Intermediate Similarity	NPC472941
0.8351	Intermediate Similarity	NPC114743
0.8351	Intermediate Similarity	NPC456
0.8351	Intermediate Similarity	NPC473153
0.8351	Intermediate Similarity	NPC195366
0.8351	Intermediate Similarity	NPC250757
0.8351	Intermediate Similarity	NPC16967
0.8351	Intermediate Similarity	NPC301534
0.8333	Intermediate Similarity	NPC256112
0.8333	Intermediate Similarity	NPC474922
0.8333	Intermediate Similarity	NPC202389
0.8333	Intermediate Similarity	NPC191521
0.8316	Intermediate Similarity	NPC329842
0.83	Intermediate Similarity	NPC293753
0.8298	Intermediate Similarity	NPC102414
0.8298	Intermediate Similarity	NPC77168
0.8298	Intermediate Similarity	NPC84271
0.8298	Intermediate Similarity	NPC314727
0.8283	Intermediate Similarity	NPC201406
0.8283	Intermediate Similarity	NPC251680
0.8265	Intermediate Similarity	NPC320306
0.8252	Intermediate Similarity	NPC220155
0.8242	Intermediate Similarity	NPC57370
0.8235	Intermediate Similarity	NPC295843
0.8235	Intermediate Similarity	NPC266570
0.8235	Intermediate Similarity	NPC189863
0.8218	Intermediate Similarity	NPC297617
0.8218	Intermediate Similarity	NPC112009
0.8211	Intermediate Similarity	NPC477147
0.8211	Intermediate Similarity	NPC477149
0.8211	Intermediate Similarity	NPC469400
0.82	Intermediate Similarity	NPC99411
0.8191	Intermediate Similarity	NPC229612
0.8191	Intermediate Similarity	NPC24816
0.8191	Intermediate Similarity	NPC7280
0.819	Intermediate Similarity	NPC262083
0.819	Intermediate Similarity	NPC474315
0.819	Intermediate Similarity	NPC471484
0.8182	Intermediate Similarity	NPC186810
0.8182	Intermediate Similarity	NPC478056
0.8172	Intermediate Similarity	NPC131813
0.8172	Intermediate Similarity	NPC474970
0.8163	Intermediate Similarity	NPC88009
0.8163	Intermediate Similarity	NPC7124
0.8163	Intermediate Similarity	NPC328371
0.8163	Intermediate Similarity	NPC117133
0.8155	Intermediate Similarity	NPC79298
0.8155	Intermediate Similarity	NPC43063
0.8152	Intermediate Similarity	NPC231310
0.8144	Intermediate Similarity	NPC57117
0.8144	Intermediate Similarity	NPC201725
0.8144	Intermediate Similarity	NPC49670
0.8132	Intermediate Similarity	NPC470049
0.8132	Intermediate Similarity	NPC2524
0.8125	Intermediate Similarity	NPC234335
0.8125	Intermediate Similarity	NPC177641
0.8125	Intermediate Similarity	NPC477574
0.8125	Intermediate Similarity	NPC72845
0.8119	Intermediate Similarity	NPC155332
0.8119	Intermediate Similarity	NPC114540
0.8119	Intermediate Similarity	NPC234892
0.8119	Intermediate Similarity	NPC32577
0.8111	Intermediate Similarity	NPC281880
0.8105	Intermediate Similarity	NPC50488
0.8105	Intermediate Similarity	NPC214387
0.8105	Intermediate Similarity	NPC474396
0.8105	Intermediate Similarity	NPC177141
0.8105	Intermediate Similarity	NPC16265
0.81	Intermediate Similarity	NPC470074
0.81	Intermediate Similarity	NPC476299
0.81	Intermediate Similarity	NPC287833
0.81	Intermediate Similarity	NPC474012
0.81	Intermediate Similarity	NPC266955
0.81	Intermediate Similarity	NPC476274
0.81	Intermediate Similarity	NPC327431
0.81	Intermediate Similarity	NPC227865
0.809	Intermediate Similarity	NPC318136
0.8085	Intermediate Similarity	NPC159046
0.8085	Intermediate Similarity	NPC233836
0.8085	Intermediate Similarity	NPC187376
0.8085	Intermediate Similarity	NPC166857
0.8081	Intermediate Similarity	NPC202705
0.8081	Intermediate Similarity	NPC210337
0.8081	Intermediate Similarity	NPC476253
0.8077	Intermediate Similarity	NPC275060
0.8077	Intermediate Similarity	NPC304276
0.8077	Intermediate Similarity	NPC137462
0.8065	Intermediate Similarity	NPC266511
0.8065	Intermediate Similarity	NPC35933
0.8065	Intermediate Similarity	NPC474013
0.8061	Intermediate Similarity	NPC162001
0.8061	Intermediate Similarity	NPC45324
0.8061	Intermediate Similarity	NPC222845
0.8061	Intermediate Similarity	NPC318282
0.8061	Intermediate Similarity	NPC173875
0.8061	Intermediate Similarity	NPC470016
0.8061	Intermediate Similarity	NPC183012
0.8061	Intermediate Similarity	NPC171395
0.8061	Intermediate Similarity	NPC174948
0.8061	Intermediate Similarity	NPC469995
0.8061	Intermediate Similarity	NPC139459
0.8061	Intermediate Similarity	NPC317586
0.8043	Intermediate Similarity	NPC79945
0.8043	Intermediate Similarity	NPC476927
0.8041	Intermediate Similarity	NPC53555
0.8041	Intermediate Similarity	NPC107674
0.8041	Intermediate Similarity	NPC170220
0.8041	Intermediate Similarity	NPC139692
0.8041	Intermediate Similarity	NPC69454
0.8041	Intermediate Similarity	NPC141497
0.8041	Intermediate Similarity	NPC134826
0.8039	Intermediate Similarity	NPC476237
0.8039	Intermediate Similarity	NPC180204
0.8022	Intermediate Similarity	NPC159148
0.8022	Intermediate Similarity	NPC6663
0.8022	Intermediate Similarity	NPC170303
0.8021	Intermediate Similarity	NPC111585
0.8021	Intermediate Similarity	NPC148414
0.8021	Intermediate Similarity	NPC175628
0.802	Intermediate Similarity	NPC295110
0.802	Intermediate Similarity	NPC25177
0.802	Intermediate Similarity	NPC247701
0.802	Intermediate Similarity	NPC476223
0.802	Intermediate Similarity	NPC268829
0.802	Intermediate Similarity	NPC224720
0.802	Intermediate Similarity	NPC222875
0.802	Intermediate Similarity	NPC115899
0.802	Intermediate Similarity	NPC476240
0.802	Intermediate Similarity	NPC472924
0.802	Intermediate Similarity	NPC282524
0.802	Intermediate Similarity	NPC473160
0.8	Intermediate Similarity	NPC242767
0.8	Intermediate Similarity	NPC103051
0.8	Intermediate Similarity	NPC104560
0.8	Intermediate Similarity	NPC325229
0.8	Intermediate Similarity	NPC474440
0.8	Intermediate Similarity	NPC278673
0.8	Intermediate Similarity	NPC197386
0.8	Intermediate Similarity	NPC472870
0.8	Intermediate Similarity	NPC75389
0.8	Intermediate Similarity	NPC477813
0.8	Intermediate Similarity	NPC275086
0.8	Intermediate Similarity	NPC242864
0.7981	Intermediate Similarity	NPC91034
0.7981	Intermediate Similarity	NPC472925
0.798	Intermediate Similarity	NPC54248
0.798	Intermediate Similarity	NPC234993
0.798	Intermediate Similarity	NPC249954
0.798	Intermediate Similarity	NPC242848
0.798	Intermediate Similarity	NPC134072
0.798	Intermediate Similarity	NPC276103
0.7979	Intermediate Similarity	NPC55309
0.7979	Intermediate Similarity	NPC28252
0.7979	Intermediate Similarity	NPC475069
0.7979	Intermediate Similarity	NPC175145
0.7959	Intermediate Similarity	NPC91010
0.7959	Intermediate Similarity	NPC104925

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 NPC190713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1195
0.2-0.3	3616
0.3-0.4	2682
0.4-0.5	1034
0.5-0.6	232
0.6-0.7	225
0.7-0.8	11
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
0.8283	Intermediate Similarity	NPD7640	Approved
0.8283	Intermediate Similarity	NPD7639	Approved
0.8182	Intermediate Similarity	NPD7638	Approved
0.7822	Intermediate Similarity	NPD4225	Approved
0.7658	Intermediate Similarity	NPD7115	Discovery
0.7596	Intermediate Similarity	NPD7632	Discontinued
0.7576	Intermediate Similarity	NPD6079	Approved
0.7576	Intermediate Similarity	NPD7515	Phase 2
0.7551	Intermediate Similarity	NPD5328	Approved
0.7426	Intermediate Similarity	NPD7748	Approved
0.7423	Intermediate Similarity	NPD3618	Phase 1
0.7423	Intermediate Similarity	NPD5279	Phase 3
0.7407	Intermediate Similarity	NPD6899	Approved
0.7407	Intermediate Similarity	NPD6881	Approved
0.7383	Intermediate Similarity	NPD7128	Approved
0.7383	Intermediate Similarity	NPD6675	Approved
0.7383	Intermediate Similarity	NPD6402	Approved
0.7383	Intermediate Similarity	NPD5739	Approved
0.7374	Intermediate Similarity	NPD6051	Approved
0.734	Intermediate Similarity	NPD7525	Registered
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7315	Intermediate Similarity	NPD5697	Approved
0.7282	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5221	Approved
0.7282	Intermediate Similarity	NPD5222	Approved
0.7273	Intermediate Similarity	NPD7102	Approved
0.7273	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD6883	Approved
0.7264	Intermediate Similarity	NPD5211	Phase 2
0.7248	Intermediate Similarity	NPD7320	Approved
0.7248	Intermediate Similarity	NPD6011	Approved
0.7241	Intermediate Similarity	NPD7503	Approved
0.7238	Intermediate Similarity	NPD6404	Discontinued
0.7228	Intermediate Similarity	NPD5281	Approved
0.7228	Intermediate Similarity	NPD5284	Approved
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7216	Intermediate Similarity	NPD4786	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7212	Intermediate Similarity	NPD5173	Approved
0.7212	Intermediate Similarity	NPD7902	Approved
0.7207	Intermediate Similarity	NPD8130	Phase 1
0.7207	Intermediate Similarity	NPD6649	Approved
0.7207	Intermediate Similarity	NPD6847	Approved
0.7207	Intermediate Similarity	NPD6617	Approved
0.7207	Intermediate Similarity	NPD6869	Approved
0.7207	Intermediate Similarity	NPD6650	Approved
0.7188	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5695	Phase 3
0.7182	Intermediate Similarity	NPD6013	Approved
0.7182	Intermediate Similarity	NPD6372	Approved
0.7182	Intermediate Similarity	NPD6373	Approved
0.7182	Intermediate Similarity	NPD6012	Approved
0.7182	Intermediate Similarity	NPD6014	Approved
0.7174	Intermediate Similarity	NPD6942	Approved
0.7174	Intermediate Similarity	NPD8264	Approved
0.7174	Intermediate Similarity	NPD7339	Approved
0.7157	Intermediate Similarity	NPD4202	Approved
0.7156	Intermediate Similarity	NPD5701	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5141	Approved
0.7115	Intermediate Similarity	NPD4697	Phase 3
0.71	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5737	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7059	Intermediate Similarity	NPD6050	Approved
0.7059	Intermediate Similarity	NPD6411	Approved
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7645	Phase 2
0.7048	Intermediate Similarity	NPD4755	Approved
0.7041	Intermediate Similarity	NPD3133	Approved
0.7041	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3666	Approved
0.7041	Intermediate Similarity	NPD3665	Phase 1
0.701	Intermediate Similarity	NPD3667	Approved
0.7009	Intermediate Similarity	NPD5223	Approved
0.699	Remote Similarity	NPD5779	Approved
0.699	Remote Similarity	NPD5778	Approved
0.6983	Remote Similarity	NPD7327	Approved
0.6983	Remote Similarity	NPD7328	Approved
0.697	Remote Similarity	NPD1696	Phase 3
0.6961	Remote Similarity	NPD5692	Phase 3
0.6961	Remote Similarity	NPD5785	Approved
0.6957	Remote Similarity	NPD6868	Approved
0.6947	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD6695	Phase 3
0.6937	Remote Similarity	NPD6686	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6903	Approved
0.693	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7900	Approved
0.6923	Remote Similarity	NPD7516	Approved
0.6916	Remote Similarity	NPD4700	Approved
0.6916	Remote Similarity	NPD6648	Approved
0.6915	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5280	Approved
0.69	Remote Similarity	NPD4694	Approved
0.6893	Remote Similarity	NPD8035	Phase 2
0.6893	Remote Similarity	NPD8034	Phase 2
0.6893	Remote Similarity	NPD5694	Approved
0.6893	Remote Similarity	NPD5693	Phase 1
0.6882	Remote Similarity	NPD6926	Approved
0.6882	Remote Similarity	NPD6924	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6875	Remote Similarity	NPD6929	Approved
0.6875	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4195	Approved
0.6869	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8294	Approved
0.6864	Remote Similarity	NPD8377	Approved
0.6863	Remote Similarity	NPD6101	Approved
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4753	Phase 2
0.6863	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5344	Discontinued
0.6838	Remote Similarity	NPD6335	Approved
0.6832	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5696	Approved
0.681	Remote Similarity	NPD6274	Approved
0.6807	Remote Similarity	NPD8379	Approved
0.6807	Remote Similarity	NPD8296	Approved
0.6807	Remote Similarity	NPD8335	Approved
0.6807	Remote Similarity	NPD8033	Approved
0.6807	Remote Similarity	NPD8380	Approved
0.6807	Remote Similarity	NPD8378	Approved
0.6804	Remote Similarity	NPD6930	Phase 2
0.6804	Remote Similarity	NPD7332	Phase 2
0.6804	Remote Similarity	NPD6931	Approved
0.6804	Remote Similarity	NPD7509	Discontinued
0.6796	Remote Similarity	NPD5207	Approved
0.678	Remote Similarity	NPD7101	Approved
0.678	Remote Similarity	NPD7100	Approved
0.6771	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5362	Discontinued
0.6752	Remote Similarity	NPD6009	Approved
0.6752	Remote Similarity	NPD6317	Approved
0.6737	Remote Similarity	NPD6933	Approved
0.6733	Remote Similarity	NPD5690	Phase 2
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4623	Approved
0.6733	Remote Similarity	NPD4519	Discontinued
0.6727	Remote Similarity	NPD4754	Approved
0.6721	Remote Similarity	NPD7507	Approved
0.6699	Remote Similarity	NPD6080	Approved
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6698	Remote Similarity	NPD5210	Approved
0.6698	Remote Similarity	NPD4629	Approved
0.6696	Remote Similarity	NPD6053	Discontinued
0.6695	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6637	Remote Similarity	NPD5128	Approved
0.6637	Remote Similarity	NPD5168	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6635	Remote Similarity	NPD7838	Discovery
0.6634	Remote Similarity	NPD5329	Approved
0.6634	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7514	Phase 3
0.6633	Remote Similarity	NPD4748	Discontinued
0.6633	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6923	Approved
0.663	Remote Similarity	NPD6922	Approved
0.6607	Remote Similarity	NPD4768	Approved
0.6607	Remote Similarity	NPD4767	Approved
0.6607	Remote Similarity	NPD6008	Approved
0.6598	Remote Similarity	NPD7145	Approved
0.6583	Remote Similarity	NPD6319	Approved
0.6566	Remote Similarity	NPD6898	Phase 1

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