NPASS Compound

Structure

CID238992 OpenBabel06191716042D 35 39 0 0 1 0 0 0 0 0999 V2000 -2.3202 3.5263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7687 3.2177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8195 -2.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7707 -2.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4713 0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6476 0.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6476 -1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1189 -0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2951 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 -1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 2.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4713 2.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2951 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 1.4268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4713 -1.4268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6476 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1189 -1.4268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4713 1.4268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8238 -0.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6476 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6476 2.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2951 -1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4713 -0.4756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8238 -0.4756 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 -1.6476 0.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1189 0.4756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9427 -1.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2951 0.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 -1.4268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4713 -0.4756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 1 0 0 0 19 26 1 0 0 0 0 19 27 1 6 0 0 0 20 27 1 6 0 0 0 20 28 1 0 0 0 0 21 26 1 0 0 0 0 21 32 1 6 0 0 0 22 30 1 1 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 1 0 0 0 23 34 1 0 0 0 0 24 30 1 1 0 0 0 24 35 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.37
Volume:	525.968
LogP:	4.092
LogD:	3.998
LogS:	-4.033
# Rotatable Bonds:	1
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	5.13
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.956
MDCK Permeability:	1.8322542018722743e-05
Pgp-inhibitor:	0.17
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.786
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.365
Plasma Protein Binding (PPB):	89.54134368896484%
Volume Distribution (VD):	0.896
Pgp-substrate:	8.840424537658691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	5.068
Half-life (T1/2):	0.297

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.963
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.17
Carcinogencity:	0.135
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC238992

Natural Product ID:	NPC238992
*Common Name:**	A1-Barrigenol
IUPAC Name:	(3S,4aR,6aR,6bS,7R,8S,8aS,9S,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,7,8,9-tetrol
Synonyms:	A1-Barrigenol
Standard InCHIKey:	MBKUYULYIBPFSF-OJSXYETASA-N
Standard InCHI:	InChI=1S/C30H50O5/c1-25(2)14-18-17-8-9-20-27(5)12-11-21(32)26(3,4)19(27)10-13-28(20,6)29(17,7)23(34)24(35)30(18,16-31)22(33)15-25/h8,18-24,31-35H,9-16H2,1-7H3/t18-,19-,20+,21-,22-,23-,24+,27-,28+,29-,30+/m0/s1
SMILES:	CC1(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)[C@H]([C@H]([C@@]2(CO)[C@H](C1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518227
PubChem CID:	12299984
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
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	n.a.	n.a.	PMID[15620235]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	Nanning City, Guangxi Province, People's Republic of China	1997-Jan	PMID[17190442]
NPO40059	Camellia crapnelliana	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29064696]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20274	Cynanchum formosanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20056	Pinus monophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8121	Symplocos chinensis	Species	Symplocaceae	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	6
Others	1

Activity Type	# Activity
Cell Line	5
CELL-LINE	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[480216]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[480216]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[480216]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[480216]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[480216]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	16790.0	nM	PMID[480217]
NPT21742	CELL-LINE	L02	Homo sapiens	Activity	<	50.0	%	PMID[480217]

☑ 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 NPC238992 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	228
0.1-0.2	1737
0.2-0.3	5925
0.3-0.4	15572
0.4-0.5	8669
0.5-0.6	4936
0.6-0.7	3846
0.7-0.8	1420
0.8-0.85	261
0.85-0.9	65
0.9-0.95	30
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9872	High Similarity	NPC159168
0.9872	High Similarity	NPC253402
0.975	High Similarity	NPC237344
0.9744	High Similarity	NPC47763
0.9359	High Similarity	NPC53744
0.9231	High Similarity	NPC470396
0.9231	High Similarity	NPC99168
0.9231	High Similarity	NPC22955
0.9231	High Similarity	NPC196753
0.9231	High Similarity	NPC253807
0.9231	High Similarity	NPC474989
0.9231	High Similarity	NPC230295
0.9231	High Similarity	NPC98386
0.9231	High Similarity	NPC158662
0.9231	High Similarity	NPC300499
0.9167	High Similarity	NPC259875
0.9167	High Similarity	NPC187785
0.9114	High Similarity	NPC291379
0.9103	High Similarity	NPC34177
0.9103	High Similarity	NPC101475
0.9103	High Similarity	NPC477924
0.9103	High Similarity	NPC40394
0.9103	High Similarity	NPC157996
0.8974	High Similarity	NPC27765
0.8974	High Similarity	NPC274079
0.8974	High Similarity	NPC477925
0.8974	High Similarity	NPC30590
0.8974	High Similarity	NPC290598
0.8974	High Similarity	NPC122418
0.8974	High Similarity	NPC106364
0.8974	High Similarity	NPC265328
0.8974	High Similarity	NPC120098
0.8929	High Similarity	NPC470620
0.8902	High Similarity	NPC82538
0.8902	High Similarity	NPC237795
0.8889	High Similarity	NPC242350
0.8846	High Similarity	NPC477923
0.8846	High Similarity	NPC34700
0.8846	High Similarity	NPC66566
0.8846	High Similarity	NPC138374
0.8765	High Similarity	NPC287749
0.8765	High Similarity	NPC295131
0.8764	High Similarity	NPC73004
0.8764	High Similarity	NPC173744
0.8764	High Similarity	NPC204961
0.875	High Similarity	NPC145667
0.875	High Similarity	NPC32407
0.875	High Similarity	NPC231063
0.875	High Similarity	NPC299996
0.875	High Similarity	NPC263548
0.875	High Similarity	NPC88116
0.875	High Similarity	NPC282395
0.875	High Similarity	NPC20235
0.8721	High Similarity	NPC105495
0.8718	High Similarity	NPC100334
0.8675	High Similarity	NPC207013
0.8667	High Similarity	NPC247139
0.8667	High Similarity	NPC9613
0.8659	High Similarity	NPC116202
0.8659	High Similarity	NPC474531
0.8652	High Similarity	NPC96916
0.8652	High Similarity	NPC32118
0.8625	High Similarity	NPC90979
0.8625	High Similarity	NPC472805
0.8625	High Similarity	NPC130136
0.8608	High Similarity	NPC291503
0.8571	High Similarity	NPC111214
0.8571	High Similarity	NPC271614
0.8571	High Similarity	NPC29765
0.8556	High Similarity	NPC19376
0.8556	High Similarity	NPC201657
0.8556	High Similarity	NPC207922
0.8556	High Similarity	NPC259733
0.8556	High Similarity	NPC25848
0.8556	High Similarity	NPC158371
0.8556	High Similarity	NPC307282
0.8556	High Similarity	NPC305464
0.8554	High Similarity	NPC30166
0.8554	High Similarity	NPC304285
0.8537	High Similarity	NPC236112
0.8523	High Similarity	NPC52021
0.8523	High Similarity	NPC84319
0.8523	High Similarity	NPC300351
0.8523	High Similarity	NPC71074
0.8523	High Similarity	NPC235884
0.8523	High Similarity	NPC472149
0.8523	High Similarity	NPC25299
0.8523	High Similarity	NPC306541
0.8519	High Similarity	NPC72507
0.8481	Intermediate Similarity	NPC243342
0.8481	Intermediate Similarity	NPC471797
0.8481	Intermediate Similarity	NPC91858
0.8481	Intermediate Similarity	NPC477138
0.8478	Intermediate Similarity	NPC476195
0.8478	Intermediate Similarity	NPC474190
0.8478	Intermediate Similarity	NPC35239
0.8478	Intermediate Similarity	NPC473790
0.8462	Intermediate Similarity	NPC261935
0.8462	Intermediate Similarity	NPC43686
0.8462	Intermediate Similarity	NPC259788
0.8462	Intermediate Similarity	NPC255589
0.8462	Intermediate Similarity	NPC106112
0.8427	Intermediate Similarity	NPC74855
0.8427	Intermediate Similarity	NPC136313
0.8427	Intermediate Similarity	NPC275809
0.8427	Intermediate Similarity	NPC229281
0.8427	Intermediate Similarity	NPC474806
0.8427	Intermediate Similarity	NPC307335
0.8427	Intermediate Similarity	NPC133579
0.8409	Intermediate Similarity	NPC49320
0.8409	Intermediate Similarity	NPC470589
0.8409	Intermediate Similarity	NPC126369
0.8409	Intermediate Similarity	NPC130278
0.8409	Intermediate Similarity	NPC111110
0.8395	Intermediate Similarity	NPC471798
0.8391	Intermediate Similarity	NPC475664
0.8391	Intermediate Similarity	NPC67872
0.8387	Intermediate Similarity	NPC476132
0.8387	Intermediate Similarity	NPC256247
0.8372	Intermediate Similarity	NPC137306
0.8372	Intermediate Similarity	NPC24277
0.8372	Intermediate Similarity	NPC213412
0.8372	Intermediate Similarity	NPC84121
0.837	Intermediate Similarity	NPC477876
0.837	Intermediate Similarity	NPC477875
0.8354	Intermediate Similarity	NPC211009
0.8354	Intermediate Similarity	NPC471799
0.8354	Intermediate Similarity	NPC182717
0.8353	Intermediate Similarity	NPC185568
0.8352	Intermediate Similarity	NPC473158
0.8352	Intermediate Similarity	NPC88847
0.8333	Intermediate Similarity	NPC215700
0.8333	Intermediate Similarity	NPC248886
0.8333	Intermediate Similarity	NPC87095
0.8333	Intermediate Similarity	NPC114159
0.8333	Intermediate Similarity	NPC191412
0.8333	Intermediate Similarity	NPC6818
0.8333	Intermediate Similarity	NPC92801
0.8315	Intermediate Similarity	NPC187722
0.8313	Intermediate Similarity	NPC236237
0.8313	Intermediate Similarity	NPC102253
0.8313	Intermediate Similarity	NPC13554
0.8313	Intermediate Similarity	NPC322313
0.8298	Intermediate Similarity	NPC273668
0.8295	Intermediate Similarity	NPC143232
0.8295	Intermediate Similarity	NPC198664
0.8295	Intermediate Similarity	NPC121798
0.8295	Intermediate Similarity	NPC263393
0.8295	Intermediate Similarity	NPC61543
0.8295	Intermediate Similarity	NPC225585
0.8295	Intermediate Similarity	NPC127689
0.8295	Intermediate Similarity	NPC234346
0.8295	Intermediate Similarity	NPC290972
0.8295	Intermediate Similarity	NPC25906
0.8295	Intermediate Similarity	NPC64872
0.8295	Intermediate Similarity	NPC293048
0.8295	Intermediate Similarity	NPC59263
0.8295	Intermediate Similarity	NPC270768
0.8295	Intermediate Similarity	NPC130520
0.8295	Intermediate Similarity	NPC274330
0.8293	Intermediate Similarity	NPC167037
0.8293	Intermediate Similarity	NPC102708
0.8293	Intermediate Similarity	NPC244385
0.8293	Intermediate Similarity	NPC167891
0.8293	Intermediate Similarity	NPC6978
0.8293	Intermediate Similarity	NPC83351
0.8293	Intermediate Similarity	NPC138621
0.828	Intermediate Similarity	NPC254567
0.828	Intermediate Similarity	NPC474571
0.8276	Intermediate Similarity	NPC474657
0.8276	Intermediate Similarity	NPC186145
0.8276	Intermediate Similarity	NPC73064
0.8272	Intermediate Similarity	NPC106432
0.8256	Intermediate Similarity	NPC191965
0.8256	Intermediate Similarity	NPC133954
0.8242	Intermediate Similarity	NPC198245
0.8235	Intermediate Similarity	NPC317458
0.8228	Intermediate Similarity	NPC242001
0.8228	Intermediate Similarity	NPC167706
0.8228	Intermediate Similarity	NPC242992
0.8228	Intermediate Similarity	NPC301226
0.8222	Intermediate Similarity	NPC202728
0.8222	Intermediate Similarity	NPC158059
0.8222	Intermediate Similarity	NPC118519
0.8214	Intermediate Similarity	NPC476646
0.8202	Intermediate Similarity	NPC92885
0.8202	Intermediate Similarity	NPC77796
0.8202	Intermediate Similarity	NPC473956
0.8202	Intermediate Similarity	NPC18872
0.8202	Intermediate Similarity	NPC210037
0.8202	Intermediate Similarity	NPC120968
0.8202	Intermediate Similarity	NPC471432
0.8202	Intermediate Similarity	NPC477872
0.8202	Intermediate Similarity	NPC290614
0.8202	Intermediate Similarity	NPC471433
0.8202	Intermediate Similarity	NPC475751
0.8202	Intermediate Similarity	NPC7260
0.8202	Intermediate Similarity	NPC227467
0.8202	Intermediate Similarity	NPC273621
0.8202	Intermediate Similarity	NPC476226

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 NPC238992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	2017
0.2-0.3	4090
0.3-0.4	2049
0.4-0.5	449
0.5-0.6	198
0.6-0.7	141
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9114	High Similarity	NPD7645	Phase 2
0.8313	Intermediate Similarity	NPD7525	Registered
0.7927	Intermediate Similarity	NPD7339	Approved
0.7927	Intermediate Similarity	NPD6942	Approved
0.7912	Intermediate Similarity	NPD7515	Phase 2
0.7831	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.7412	Intermediate Similarity	NPD6933	Approved
0.7333	Intermediate Similarity	NPD4786	Approved
0.7303	Intermediate Similarity	NPD3667	Approved
0.7188	Intermediate Similarity	NPD7900	Approved
0.7188	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6926	Approved
0.7176	Intermediate Similarity	NPD6924	Approved
0.7174	Intermediate Similarity	NPD3618	Phase 1
0.7128	Intermediate Similarity	NPD5328	Approved
0.7108	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7524	Approved
0.7093	Intermediate Similarity	NPD8264	Approved
0.7079	Intermediate Similarity	NPD7509	Discontinued
0.7065	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6079	Approved
0.6977	Remote Similarity	NPD4784	Approved
0.6977	Remote Similarity	NPD4785	Approved
0.697	Remote Similarity	NPD4755	Approved
0.6966	Remote Similarity	NPD6929	Approved
0.6957	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7152	Approved
0.6941	Remote Similarity	NPD4243	Approved
0.6941	Remote Similarity	NPD7151	Approved
0.6941	Remote Similarity	NPD7150	Approved
0.6915	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6399	Phase 3
0.6907	Remote Similarity	NPD4202	Approved
0.6905	Remote Similarity	NPD6922	Approved
0.6905	Remote Similarity	NPD6923	Approved
0.6889	Remote Similarity	NPD4748	Discontinued
0.6889	Remote Similarity	NPD6931	Approved
0.6889	Remote Similarity	NPD6930	Phase 2
0.6848	Remote Similarity	NPD6695	Phase 3
0.6832	Remote Similarity	NPD4696	Approved
0.6832	Remote Similarity	NPD5285	Approved
0.6832	Remote Similarity	NPD5286	Approved
0.6832	Remote Similarity	NPD4700	Approved
0.6824	Remote Similarity	NPD7144	Approved
0.6824	Remote Similarity	NPD7143	Approved
0.6804	Remote Similarity	NPD8035	Phase 2
0.6804	Remote Similarity	NPD8034	Phase 2
0.6792	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3665	Phase 1
0.6774	Remote Similarity	NPD3133	Approved
0.6774	Remote Similarity	NPD3668	Phase 3
0.6774	Remote Similarity	NPD3666	Approved
0.6742	Remote Similarity	NPD6932	Approved
0.6742	Remote Similarity	NPD5776	Phase 2
0.6742	Remote Similarity	NPD6925	Approved
0.6733	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD4225	Approved
0.67	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5222	Approved
0.67	Remote Similarity	NPD5221	Approved
0.67	Remote Similarity	NPD4697	Phase 3
0.6699	Remote Similarity	NPD5225	Approved
0.6699	Remote Similarity	NPD5226	Approved
0.6699	Remote Similarity	NPD5211	Phase 2
0.6699	Remote Similarity	NPD4633	Approved
0.6699	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5175	Approved
0.6635	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD5173	Approved
0.6609	Remote Similarity	NPD8328	Phase 3
0.6604	Remote Similarity	NPD6412	Phase 2
0.6602	Remote Similarity	NPD5223	Approved
0.6602	Remote Similarity	NPD4159	Approved
0.6598	Remote Similarity	NPD4753	Phase 2
0.6598	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6683	Phase 2
0.6579	Remote Similarity	NPD8033	Approved
0.6574	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD5141	Approved
0.6562	Remote Similarity	NPD7750	Discontinued
0.6549	Remote Similarity	NPD7516	Approved
0.6542	Remote Similarity	NPD6899	Approved
0.6542	Remote Similarity	NPD7320	Approved
0.6542	Remote Similarity	NPD6881	Approved
0.6526	Remote Similarity	NPD6893	Approved
0.6522	Remote Similarity	NPD7332	Phase 2
0.6522	Remote Similarity	NPD7514	Phase 3
0.6522	Remote Similarity	NPD4695	Discontinued
0.6518	Remote Similarity	NPD7115	Discovery
0.6517	Remote Similarity	NPD4190	Phase 3
0.6517	Remote Similarity	NPD5275	Approved
0.6509	Remote Similarity	NPD4768	Approved
0.6509	Remote Similarity	NPD4767	Approved
0.6491	Remote Similarity	NPD8294	Approved
0.6491	Remote Similarity	NPD8377	Approved
0.6484	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD4754	Approved
0.6465	Remote Similarity	NPD6411	Approved
0.6463	Remote Similarity	NPD368	Approved
0.646	Remote Similarity	NPD7328	Approved
0.646	Remote Similarity	NPD7327	Approved
0.6455	Remote Similarity	NPD8297	Approved
0.6452	Remote Similarity	NPD6902	Approved
0.6452	Remote Similarity	NPD6898	Phase 1
0.6449	Remote Similarity	NPD5697	Approved
0.6449	Remote Similarity	NPD5701	Approved
0.6435	Remote Similarity	NPD8378	Approved
0.6435	Remote Similarity	NPD8296	Approved
0.6435	Remote Similarity	NPD8335	Approved
0.6435	Remote Similarity	NPD8380	Approved
0.6435	Remote Similarity	NPD8379	Approved
0.6422	Remote Similarity	NPD6883	Approved
0.6422	Remote Similarity	NPD7290	Approved
0.6422	Remote Similarity	NPD7102	Approved
0.6413	Remote Similarity	NPD4195	Approved
0.6408	Remote Similarity	NPD5290	Discontinued
0.6389	Remote Similarity	NPD5128	Approved
0.6389	Remote Similarity	NPD4730	Approved
0.6389	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6364	Remote Similarity	NPD6869	Approved
0.6364	Remote Similarity	NPD6847	Approved
0.6364	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD6617	Approved
0.6339	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6012	Approved
0.633	Remote Similarity	NPD6014	Approved
0.633	Remote Similarity	NPD6013	Approved
0.6327	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6084	Phase 2
0.6311	Remote Similarity	NPD6083	Phase 2
0.6306	Remote Similarity	NPD6882	Approved
0.63	Remote Similarity	NPD7087	Discontinued
0.6293	Remote Similarity	NPD7503	Approved
0.6289	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5279	Phase 3
0.6286	Remote Similarity	NPD5344	Discontinued
0.6275	Remote Similarity	NPD4629	Approved
0.6275	Remote Similarity	NPD5210	Approved
0.6273	Remote Similarity	NPD5248	Approved
0.6273	Remote Similarity	NPD5250	Approved
0.6273	Remote Similarity	NPD5247	Approved
0.6273	Remote Similarity	NPD5251	Approved
0.6273	Remote Similarity	NPD5249	Phase 3
0.6263	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD4632	Approved
0.6239	Remote Similarity	NPD6011	Approved
0.6216	Remote Similarity	NPD5215	Approved
0.6216	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5216	Approved
0.6216	Remote Similarity	NPD5217	Approved
0.6211	Remote Similarity	NPD4221	Approved
0.6211	Remote Similarity	NPD4223	Phase 3
0.62	Remote Similarity	NPD3168	Discontinued
0.6196	Remote Similarity	NPD6116	Phase 1
0.6186	Remote Similarity	NPD5329	Approved
0.617	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4788	Approved
0.6126	Remote Similarity	NPD5135	Approved
0.6126	Remote Similarity	NPD5169	Approved
0.6126	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5330	Approved
0.6122	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD6409	Approved
0.6122	Remote Similarity	NPD7521	Approved
0.6122	Remote Similarity	NPD6684	Approved
0.6122	Remote Similarity	NPD7146	Approved
0.6106	Remote Similarity	NPD8133	Approved
0.61	Remote Similarity	NPD6051	Approved
0.6091	Remote Similarity	NPD6686	Approved
0.6091	Remote Similarity	NPD5168	Approved
0.6091	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6117	Approved
0.6083	Remote Similarity	NPD7507	Approved
0.6082	Remote Similarity	NPD4197	Approved
0.6075	Remote Similarity	NPD7632	Discontinued
0.6071	Remote Similarity	NPD5127	Approved
0.6068	Remote Similarity	NPD6054	Approved
0.6068	Remote Similarity	NPD6059	Approved
0.6068	Remote Similarity	NPD6319	Approved
0.6067	Remote Similarity	NPD4787	Phase 1
0.6061	Remote Similarity	NPD3573	Approved
0.6058	Remote Similarity	NPD7614	Phase 1
0.604	Remote Similarity	NPD7136	Phase 2
0.6	Remote Similarity	NPD4809	Clinical (unspecified phase)

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