NPASS Compound

Structure

NPC279410 OpenBabel07101718292D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.8767 -5.3851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1336 -2.8785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1733 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1996 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3361 -1.9261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2904 0.8895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2816 -3.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0052 -4.1318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4840 -2.5279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1848 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6125 0.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8027 -5.0842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4101 -2.2270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5263 -5.7357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6125 -1.2746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 0.4868 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 3.3729 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3239 -6.6881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4524 -5.4348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 25 1 0 0 0 0 20 2 1 1 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 29 1 1 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 6 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	5.703
LogD:	3.922
LogS:	-4.24
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	5.171
Fsp3:	0.833
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:	-5.066
MDCK Permeability:	1.8015753084910102e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.747
30% Bioavailability (F30%):	0.514

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.354
Plasma Protein Binding (PPB):	93.83560180664062%
Volume Distribution (VD):	0.649
Pgp-substrate:	4.3641767501831055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.35
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.646
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.444
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.44
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	3.066
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.739
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.785
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.928
Carcinogencity:	0.392
Eye Corrosion:	0.03
Eye Irritation:	0.068
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC279410

Natural Product ID:	NPC279410
*Common Name:**	Garcihombronane H
IUPAC Name:	(E,6R)-6-[(3R,5S,8S,9R,10S,14S,17S)-3,9-dihydroxy-4,4,10,14,17-pentamethyl-1,2,3,5,6,7,8,11,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoic acid
Synonyms:	Garcihombronane H
Standard InCHIKey:	GBEVCPIJOYQRAL-DHEFQOKPSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-19(25(32)33)9-8-10-20(2)27(5)17-18-28(6)22(27)13-16-30(34)23(28)12-11-21-26(3,4)24(31)14-15-29(21,30)7/h9,13,20-21,23-24,31,34H,8,10-12,14-18H2,1-7H3,(H,32,33)/b19-9+/t20-,21+,23+,24-,27+,28-,29+,30-/m1/s1
SMILES:	C/C(=CCC[C@@H](C)[C@]1(C)CC[C@]2(C)C1=CC[C@]1([C@H]2CC[C@H]2C(C)(C)[C@@H](CC[C@]12C)O)O)/C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470245
PubChem CID:	44559182
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO20779	Garcinia hombroniana	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[527897]

☑ 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 NPC279410 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	164
0.1-0.2	1064
0.2-0.3	4143
0.3-0.4	10634
0.4-0.5	11314
0.5-0.6	6190
0.6-0.7	5677
0.7-0.8	3116
0.8-0.85	334
0.85-0.9	49
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC119562
0.9667	High Similarity	NPC99726
0.9318	High Similarity	NPC146554
0.9318	High Similarity	NPC262858
0.9318	High Similarity	NPC472240
0.914	High Similarity	NPC218107
0.9121	High Similarity	NPC476186
0.9101	High Similarity	NPC314727
0.9011	High Similarity	NPC214697
0.9011	High Similarity	NPC476304
0.9011	High Similarity	NPC38232
0.8901	High Similarity	NPC110923
0.8901	High Similarity	NPC212948
0.8901	High Similarity	NPC74296
0.883	High Similarity	NPC108078
0.883	High Similarity	NPC141401
0.883	High Similarity	NPC320306
0.8764	High Similarity	NPC261266
0.8764	High Similarity	NPC6391
0.8736	High Similarity	NPC2524
0.8723	High Similarity	NPC54248
0.8723	High Similarity	NPC276103
0.8723	High Similarity	NPC195366
0.8723	High Similarity	NPC114743
0.871	High Similarity	NPC474922
0.866	High Similarity	NPC293753
0.8646	High Similarity	NPC327431
0.8646	High Similarity	NPC470074
0.8621	High Similarity	NPC159148
0.8617	High Similarity	NPC271195
0.8571	High Similarity	NPC85742
0.8556	High Similarity	NPC474970
0.8556	High Similarity	NPC475069
0.8556	High Similarity	NPC175145
0.8542	High Similarity	NPC114274
0.8526	High Similarity	NPC190713
0.8511	High Similarity	NPC57117
0.8506	High Similarity	NPC281880
0.85	High Similarity	NPC472925
0.8495	Intermediate Similarity	NPC234335
0.8469	Intermediate Similarity	NPC136289
0.8469	Intermediate Similarity	NPC234892
0.8454	Intermediate Similarity	NPC154072
0.8454	Intermediate Similarity	NPC251680
0.8444	Intermediate Similarity	NPC109528
0.8438	Intermediate Similarity	NPC253826
0.8427	Intermediate Similarity	NPC476927
0.8427	Intermediate Similarity	NPC79945
0.8421	Intermediate Similarity	NPC276110
0.8409	Intermediate Similarity	NPC209620
0.8409	Intermediate Similarity	NPC23852
0.84	Intermediate Similarity	NPC323834
0.8387	Intermediate Similarity	NPC48010
0.8387	Intermediate Similarity	NPC469400
0.8387	Intermediate Similarity	NPC295668
0.8387	Intermediate Similarity	NPC78973
0.8384	Intermediate Similarity	NPC297617
0.8384	Intermediate Similarity	NPC95899
0.8384	Intermediate Similarity	NPC249187
0.8384	Intermediate Similarity	NPC247957
0.8384	Intermediate Similarity	NPC478057
0.837	Intermediate Similarity	NPC104560
0.837	Intermediate Similarity	NPC474668
0.8367	Intermediate Similarity	NPC295110
0.8367	Intermediate Similarity	NPC247701
0.8367	Intermediate Similarity	NPC81530
0.8367	Intermediate Similarity	NPC25177
0.8367	Intermediate Similarity	NPC472924
0.8367	Intermediate Similarity	NPC222875
0.8367	Intermediate Similarity	NPC268829
0.8352	Intermediate Similarity	NPC152808
0.8352	Intermediate Similarity	NPC293287
0.8351	Intermediate Similarity	NPC103051
0.8351	Intermediate Similarity	NPC478056
0.8333	Intermediate Similarity	NPC301534
0.8333	Intermediate Similarity	NPC302360
0.8333	Intermediate Similarity	NPC472941
0.8333	Intermediate Similarity	NPC33913
0.8333	Intermediate Similarity	NPC456
0.8333	Intermediate Similarity	NPC7124
0.8333	Intermediate Similarity	NPC250757
0.8333	Intermediate Similarity	NPC205845
0.8333	Intermediate Similarity	NPC472265
0.8316	Intermediate Similarity	NPC8993
0.8316	Intermediate Similarity	NPC470957
0.8316	Intermediate Similarity	NPC196485
0.8316	Intermediate Similarity	NPC245972
0.8316	Intermediate Similarity	NPC469406
0.8316	Intermediate Similarity	NPC105490
0.8316	Intermediate Similarity	NPC470958
0.8315	Intermediate Similarity	NPC49964
0.8315	Intermediate Similarity	NPC101462
0.8315	Intermediate Similarity	NPC256112
0.8315	Intermediate Similarity	NPC50964
0.83	Intermediate Similarity	NPC72255
0.83	Intermediate Similarity	NPC473543
0.8298	Intermediate Similarity	NPC97404
0.8298	Intermediate Similarity	NPC233116
0.8298	Intermediate Similarity	NPC475806
0.8298	Intermediate Similarity	NPC473998
0.8298	Intermediate Similarity	NPC41554
0.8298	Intermediate Similarity	NPC177641
0.8298	Intermediate Similarity	NPC473675
0.8283	Intermediate Similarity	NPC109195
0.8283	Intermediate Similarity	NPC475038
0.828	Intermediate Similarity	NPC16265
0.828	Intermediate Similarity	NPC475921
0.828	Intermediate Similarity	NPC309603
0.828	Intermediate Similarity	NPC470361
0.828	Intermediate Similarity	NPC474704
0.828	Intermediate Similarity	NPC170633
0.828	Intermediate Similarity	NPC473999
0.8265	Intermediate Similarity	NPC38855
0.8261	Intermediate Similarity	NPC474684
0.8261	Intermediate Similarity	NPC142361
0.8247	Intermediate Similarity	NPC122294
0.8242	Intermediate Similarity	NPC470360
0.8235	Intermediate Similarity	NPC472218
0.8235	Intermediate Similarity	NPC472217
0.8235	Intermediate Similarity	NPC472219
0.8229	Intermediate Similarity	NPC318282
0.8229	Intermediate Similarity	NPC476174
0.8229	Intermediate Similarity	NPC174948
0.8229	Intermediate Similarity	NPC469995
0.8229	Intermediate Similarity	NPC53565
0.8229	Intermediate Similarity	NPC279974
0.8229	Intermediate Similarity	NPC266899
0.8229	Intermediate Similarity	NPC173875
0.8222	Intermediate Similarity	NPC57370
0.8222	Intermediate Similarity	NPC474634
0.8218	Intermediate Similarity	NPC119855
0.8218	Intermediate Similarity	NPC257353
0.8218	Intermediate Similarity	NPC220217
0.8218	Intermediate Similarity	NPC149047
0.8211	Intermediate Similarity	NPC7349
0.8202	Intermediate Similarity	NPC264245
0.8202	Intermediate Similarity	NPC476646
0.8202	Intermediate Similarity	NPC170303
0.82	Intermediate Similarity	NPC97487
0.82	Intermediate Similarity	NPC160583
0.82	Intermediate Similarity	NPC189588
0.82	Intermediate Similarity	NPC10232
0.82	Intermediate Similarity	NPC187302
0.82	Intermediate Similarity	NPC196471
0.82	Intermediate Similarity	NPC112009
0.82	Intermediate Similarity	NPC36688
0.82	Intermediate Similarity	NPC473523
0.8191	Intermediate Similarity	NPC280149
0.8191	Intermediate Similarity	NPC11216
0.8191	Intermediate Similarity	NPC291484
0.8191	Intermediate Similarity	NPC221111
0.8191	Intermediate Similarity	NPC329596
0.8191	Intermediate Similarity	NPC204188
0.8191	Intermediate Similarity	NPC3345
0.8191	Intermediate Similarity	NPC80561
0.8182	Intermediate Similarity	NPC143182
0.8182	Intermediate Similarity	NPC81306
0.8182	Intermediate Similarity	NPC163372
0.8182	Intermediate Similarity	NPC302537
0.8182	Intermediate Similarity	NPC28862
0.8182	Intermediate Similarity	NPC47982
0.8182	Intermediate Similarity	NPC471412
0.8182	Intermediate Similarity	NPC30986
0.8182	Intermediate Similarity	NPC475617
0.8182	Intermediate Similarity	NPC282524
0.8182	Intermediate Similarity	NPC109546
0.8182	Intermediate Similarity	NPC84694
0.8182	Intermediate Similarity	NPC209430
0.8173	Intermediate Similarity	NPC255401
0.8173	Intermediate Similarity	NPC470076
0.8173	Intermediate Similarity	NPC472928
0.8173	Intermediate Similarity	NPC284162
0.8172	Intermediate Similarity	NPC229612
0.8172	Intermediate Similarity	NPC291665
0.8172	Intermediate Similarity	NPC133588
0.8172	Intermediate Similarity	NPC7280
0.8172	Intermediate Similarity	NPC242864
0.8172	Intermediate Similarity	NPC48107
0.8163	Intermediate Similarity	NPC275086
0.8163	Intermediate Similarity	NPC477854
0.8163	Intermediate Similarity	NPC235464
0.8163	Intermediate Similarity	NPC197386
0.8163	Intermediate Similarity	NPC325229
0.8163	Intermediate Similarity	NPC92275
0.8163	Intermediate Similarity	NPC166745
0.8163	Intermediate Similarity	NPC16021
0.8161	Intermediate Similarity	NPC132542
0.8152	Intermediate Similarity	NPC82979
0.8152	Intermediate Similarity	NPC472986
0.8152	Intermediate Similarity	NPC73038
0.8152	Intermediate Similarity	NPC155011
0.8152	Intermediate Similarity	NPC472985
0.8152	Intermediate Similarity	NPC299068
0.8152	Intermediate Similarity	NPC473226
0.8144	Intermediate Similarity	NPC249954
0.8144	Intermediate Similarity	NPC253115
0.8144	Intermediate Similarity	NPC328371
0.8144	Intermediate Similarity	NPC304899
0.8144	Intermediate Similarity	NPC173272
0.8144	Intermediate Similarity	NPC477853

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 NPC279410 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1296
0.2-0.3	3896
0.3-0.4	2564
0.4-0.5	758
0.5-0.6	181
0.6-0.7	147
0.7-0.8	162
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8454	Intermediate Similarity	NPD7640	Approved
0.8454	Intermediate Similarity	NPD7639	Approved
0.8351	Intermediate Similarity	NPD7638	Approved
0.7917	Intermediate Similarity	NPD7515	Phase 2
0.7917	Intermediate Similarity	NPD6079	Approved
0.7895	Intermediate Similarity	NPD5328	Approved
0.7889	Intermediate Similarity	NPD7525	Registered
0.7872	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4225	Approved
0.7798	Intermediate Similarity	NPD7115	Discovery
0.7766	Intermediate Similarity	NPD3618	Phase 1
0.7745	Intermediate Similarity	NPD7632	Discontinued
0.7745	Intermediate Similarity	NPD5211	Phase 2
0.7742	Intermediate Similarity	NPD4786	Approved
0.7727	Intermediate Similarity	NPD7339	Approved
0.7727	Intermediate Similarity	NPD6942	Approved
0.7714	Intermediate Similarity	NPD6899	Approved
0.7714	Intermediate Similarity	NPD6881	Approved
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.7653	Intermediate Similarity	NPD6399	Phase 3
0.7653	Intermediate Similarity	NPD4202	Approved
0.7619	Intermediate Similarity	NPD5697	Approved
0.76	Intermediate Similarity	NPD5222	Approved
0.76	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5221	Approved
0.7596	Intermediate Similarity	NPD5141	Approved
0.7576	Intermediate Similarity	NPD7748	Approved
0.757	Intermediate Similarity	NPD6883	Approved
0.757	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD7290	Approved
0.7551	Intermediate Similarity	NPD7637	Suspended
0.7549	Intermediate Similarity	NPD4696	Approved
0.7549	Intermediate Similarity	NPD5285	Approved
0.7549	Intermediate Similarity	NPD5286	Approved
0.7547	Intermediate Similarity	NPD6011	Approved
0.7547	Intermediate Similarity	NPD7320	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7525	Intermediate Similarity	NPD6084	Phase 2
0.7525	Intermediate Similarity	NPD6083	Phase 2
0.7525	Intermediate Similarity	NPD4755	Approved
0.7525	Intermediate Similarity	NPD5173	Approved
0.7523	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6931	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD6930	Phase 2
0.7477	Intermediate Similarity	NPD6012	Approved
0.7477	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6013	Approved
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7476	Intermediate Similarity	NPD5223	Approved
0.7474	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5701	Approved
0.7447	Intermediate Similarity	NPD6695	Phase 3
0.7444	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD8297	Approved
0.7431	Intermediate Similarity	NPD6882	Approved
0.7426	Intermediate Similarity	NPD4697	Phase 3
0.7404	Intermediate Similarity	NPD5225	Approved
0.7404	Intermediate Similarity	NPD5226	Approved
0.7404	Intermediate Similarity	NPD5224	Approved
0.7404	Intermediate Similarity	NPD4633	Approved
0.7391	Intermediate Similarity	NPD4195	Approved
0.7391	Intermediate Similarity	NPD6929	Approved
0.7379	Intermediate Similarity	NPD4700	Approved
0.7368	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3133	Approved
0.7358	Intermediate Similarity	NPD6008	Approved
0.7353	Intermediate Similarity	NPD7902	Approved
0.7347	Intermediate Similarity	NPD6051	Approved
0.7347	Intermediate Similarity	NPD4753	Phase 2
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5174	Approved
0.7333	Intermediate Similarity	NPD5175	Approved
0.7321	Intermediate Similarity	NPD6009	Approved
0.7312	Intermediate Similarity	NPD7514	Phase 3
0.7257	Intermediate Similarity	NPD7327	Approved
0.7257	Intermediate Similarity	NPD7328	Approved
0.7248	Intermediate Similarity	NPD4634	Approved
0.7245	Intermediate Similarity	NPD6672	Approved
0.7245	Intermediate Similarity	NPD5737	Approved
0.7222	Intermediate Similarity	NPD6926	Approved
0.7222	Intermediate Similarity	NPD6924	Approved
0.7217	Intermediate Similarity	NPD8033	Approved
0.7217	Intermediate Similarity	NPD7503	Approved
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7216	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7645	Phase 2
0.7193	Intermediate Similarity	NPD7516	Approved
0.7174	Intermediate Similarity	NPD5776	Phase 2
0.7174	Intermediate Similarity	NPD6925	Approved
0.717	Intermediate Similarity	NPD4754	Approved
0.7158	Intermediate Similarity	NPD4223	Phase 3
0.7158	Intermediate Similarity	NPD4221	Approved
0.7157	Intermediate Similarity	NPD5210	Approved
0.7157	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7157	Intermediate Similarity	NPD4629	Approved
0.7156	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5344	Discontinued
0.7143	Intermediate Similarity	NPD7750	Discontinued
0.7143	Intermediate Similarity	NPD7524	Approved
0.713	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD8377	Approved
0.713	Intermediate Similarity	NPD8294	Approved
0.7128	Intermediate Similarity	NPD7332	Phase 2
0.7115	Intermediate Similarity	NPD5696	Approved
0.7113	Intermediate Similarity	NPD6893	Approved
0.7113	Intermediate Similarity	NPD5329	Approved
0.7105	Intermediate Similarity	NPD6335	Approved
0.7097	Intermediate Similarity	NPD7145	Approved
0.7097	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD6118	Approved
0.7097	Intermediate Similarity	NPD6114	Approved
0.7097	Intermediate Similarity	NPD6697	Approved
0.7094	Intermediate Similarity	NPD7604	Phase 2
0.708	Intermediate Similarity	NPD6274	Approved
0.708	Intermediate Similarity	NPD6868	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7071	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8378	Approved
0.7069	Intermediate Similarity	NPD8379	Approved
0.7069	Intermediate Similarity	NPD8296	Approved
0.7069	Intermediate Similarity	NPD5983	Phase 2
0.7069	Intermediate Similarity	NPD8335	Approved
0.7069	Intermediate Similarity	NPD8380	Approved
0.7065	Intermediate Similarity	NPD6933	Approved
0.7064	Intermediate Similarity	NPD4730	Approved
0.7064	Intermediate Similarity	NPD4729	Approved
0.7064	Intermediate Similarity	NPD6686	Approved
0.7064	Intermediate Similarity	NPD5128	Approved
0.7059	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7900	Approved
0.7053	Intermediate Similarity	NPD6902	Approved
0.7043	Intermediate Similarity	NPD7101	Approved
0.7043	Intermediate Similarity	NPD7100	Approved
0.7041	Intermediate Similarity	NPD5279	Phase 3
0.7041	Intermediate Similarity	NPD4623	Approved
0.7041	Intermediate Similarity	NPD4519	Discontinued
0.7037	Intermediate Similarity	NPD4767	Approved
0.7037	Intermediate Similarity	NPD4768	Approved
0.7034	Intermediate Similarity	NPD7492	Approved
0.7033	Intermediate Similarity	NPD4784	Approved
0.7033	Intermediate Similarity	NPD4785	Approved
0.703	Intermediate Similarity	NPD5284	Approved
0.703	Intermediate Similarity	NPD8035	Phase 2
0.703	Intermediate Similarity	NPD8034	Phase 2
0.703	Intermediate Similarity	NPD5281	Approved
0.7018	Intermediate Similarity	NPD6317	Approved
0.701	Intermediate Similarity	NPD3668	Phase 3
0.701	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.7	Intermediate Similarity	NPD4243	Approved
0.6989	Remote Similarity	NPD6932	Approved
0.6983	Remote Similarity	NPD6054	Approved
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7507	Approved
0.6975	Remote Similarity	NPD6616	Approved
0.6975	Remote Similarity	NPD6336	Discontinued
0.697	Remote Similarity	NPD3573	Approved
0.6964	Remote Similarity	NPD6053	Discontinued
0.6961	Remote Similarity	NPD5778	Approved
0.6961	Remote Similarity	NPD5779	Approved
0.6957	Remote Similarity	NPD8264	Approved
0.6957	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD6314	Approved
0.6952	Remote Similarity	NPD5290	Discontinued
0.6947	Remote Similarity	NPD4695	Discontinued
0.6947	Remote Similarity	NPD4748	Discontinued
0.6939	Remote Similarity	NPD1696	Phase 3
0.6937	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5250	Approved
0.6937	Remote Similarity	NPD5169	Approved
0.6937	Remote Similarity	NPD5247	Approved
0.6937	Remote Similarity	NPD5135	Approved
0.6937	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5251	Approved
0.6937	Remote Similarity	NPD5248	Approved
0.6937	Remote Similarity	NPD5249	Phase 3
0.6917	Remote Similarity	NPD7078	Approved
0.6915	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5168	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