NPASS Compound

Structure

CID146615 OpenBabel06191715502D 21 23 0 0 0 0 0 0 0 0999 V2000 3.3799 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2459 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5355 -0.5290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9693 0.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5382 -0.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.2470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4088 1.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 1.1982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8399 2.0992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -0.8765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 3.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3799 2.1235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 18 2 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	4.039
LogD:	3.123
LogS:	-3.664
# Rotatable Bonds:	1
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	3.068
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.007
MDCK Permeability:	1.877119211712852e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	100.28510284423828%
Volume Distribution (VD):	0.437
Pgp-substrate:	1.929470181465149%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.258
CYP2C19-substrate:	0.517
CYP2C9-inhibitor:	0.372
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.434
CYP2D6-substrate:	0.861
CYP3A4-inhibitor:	0.266
CYP3A4-substrate:	0.254

ADMET: Excretion

Clearance (CL):	7.361
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.742
AMES Toxicity:	0.135
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.821
Skin Sensitization:	0.957
Carcinogencity:	0.585
Eye Corrosion:	0.009
Eye Irritation:	0.934
Respiratory Toxicity:	0.456

Download Data

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

Natural Product: NPC146615

Natural Product ID:	NPC146615
*Common Name:**	Bauhinoxepin H
IUPAC Name:	7-hydroxy-3-methoxy-2-methyl-5,6-dihydrobenzo[b][1]benzoxepine-1,4-dione
Synonyms:	bauhinoxepin H
Standard InCHIKey:	JVENVIUECZOPJL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-8-13(18)16-10(14(19)15(8)20-2)7-6-9-11(17)4-3-5-12(9)21-16/h3-5,17H,6-7H2,1-2H3
SMILES:	COC1=C(C)C(=O)C2=C(C1=O)CCc1c(O2)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389849
PubChem CID:	16680046
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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
NPO809	Leitneria floridana	Species	Simaroubaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11141127]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15595606]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562827]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17480099]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	roots	Phitsanulok Province, Thailand	2004-MAY	PMID[17480099]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6828	Purpura aperta	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9608	Lepraria citrina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO809	Leitneria floridana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8807	Laurentia longiflora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4382	Elmerrillia papuana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25475	Syphonota geographica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1490	Goldfussia yunnanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9881	Petrosia hebes	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4628	Aloe deltoideodonta	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8977	0tholaena aschenborniana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3357	Alnus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2455	Thermopsis mollis	Species	Fabaceae	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
MIC	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	34900.0	nM	PMID[496688]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	15700.0	nM	PMID[496688]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	>	34900.0	nM	PMID[496688]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	87400.0	nM	PMID[496688]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	11200.0	nM	PMID[496688]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	174800.0	nM	PMID[496688]
NPT27	Others	Unspecified		IC50	=	11500.0	nM	PMID[496688]

☑ 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 NPC146615 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	308
0.1-0.2	1432
0.2-0.3	4164
0.3-0.4	10382
0.4-0.5	8064
0.5-0.6	4368
0.6-0.7	7635
0.7-0.8	5716
0.8-0.85	605
0.85-0.9	20
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC98509
0.9237	High Similarity	NPC266245
0.8915	High Similarity	NPC201419
0.8881	High Similarity	NPC309452
0.879	High Similarity	NPC152159
0.8788	High Similarity	NPC119985
0.8788	High Similarity	NPC280476
0.8702	High Similarity	NPC187907
0.8623	High Similarity	NPC146679
0.8623	High Similarity	NPC184536
0.8623	High Similarity	NPC230285
0.8623	High Similarity	NPC103342
0.8623	High Similarity	NPC59951
0.8623	High Similarity	NPC103904
0.8582	High Similarity	NPC128216
0.8571	High Similarity	NPC137264
0.8561	High Similarity	NPC262094
0.8561	High Similarity	NPC136840
0.8561	High Similarity	NPC90582
0.8551	High Similarity	NPC143799
0.8551	High Similarity	NPC49242
0.8551	High Similarity	NPC152042
0.8551	High Similarity	NPC241838
0.8551	High Similarity	NPC230902
0.854	High Similarity	NPC287068
0.854	High Similarity	NPC221046
0.8511	High Similarity	NPC71210
0.8507	High Similarity	NPC189106
0.8507	High Similarity	NPC186097
0.8507	High Similarity	NPC112192
0.8507	High Similarity	NPC31872
0.8507	High Similarity	NPC164236
0.8507	High Similarity	NPC475009
0.8507	High Similarity	NPC473584
0.8507	High Similarity	NPC128348
0.8507	High Similarity	NPC475589
0.8507	High Similarity	NPC475008
0.8507	High Similarity	NPC66384
0.8507	High Similarity	NPC309717
0.8496	Intermediate Similarity	NPC247779
0.8496	Intermediate Similarity	NPC115998
0.8496	Intermediate Similarity	NPC39753
0.8489	Intermediate Similarity	NPC281207
0.8489	Intermediate Similarity	NPC269652
0.8478	Intermediate Similarity	NPC25427
0.8478	Intermediate Similarity	NPC124269
0.8478	Intermediate Similarity	NPC268691
0.8467	Intermediate Similarity	NPC29353
0.8467	Intermediate Similarity	NPC127447
0.8467	Intermediate Similarity	NPC473887
0.8467	Intermediate Similarity	NPC187826
0.8467	Intermediate Similarity	NPC124784
0.8467	Intermediate Similarity	NPC234133
0.8467	Intermediate Similarity	NPC231772
0.8467	Intermediate Similarity	NPC121243
0.8467	Intermediate Similarity	NPC240147
0.8467	Intermediate Similarity	NPC194281
0.8467	Intermediate Similarity	NPC47815
0.8467	Intermediate Similarity	NPC174999
0.8456	Intermediate Similarity	NPC125920
0.8456	Intermediate Similarity	NPC248872
0.8456	Intermediate Similarity	NPC236974
0.8456	Intermediate Similarity	NPC144027
0.8451	Intermediate Similarity	NPC329678
0.8451	Intermediate Similarity	NPC306488
0.8451	Intermediate Similarity	NPC5820
0.8451	Intermediate Similarity	NPC178343
0.8444	Intermediate Similarity	NPC203817
0.8444	Intermediate Similarity	NPC25937
0.8444	Intermediate Similarity	NPC10971
0.844	Intermediate Similarity	NPC470216
0.844	Intermediate Similarity	NPC158874
0.8433	Intermediate Similarity	NPC270369
0.8433	Intermediate Similarity	NPC5515
0.8421	Intermediate Similarity	NPC474289
0.8421	Intermediate Similarity	NPC197425
0.8417	Intermediate Similarity	NPC274784
0.8417	Intermediate Similarity	NPC78913
0.8417	Intermediate Similarity	NPC150648
0.8417	Intermediate Similarity	NPC23257
0.8417	Intermediate Similarity	NPC225153
0.8417	Intermediate Similarity	NPC222342
0.8417	Intermediate Similarity	NPC18260
0.8417	Intermediate Similarity	NPC310135
0.8417	Intermediate Similarity	NPC265871
0.8417	Intermediate Similarity	NPC20709
0.8417	Intermediate Similarity	NPC329203
0.8406	Intermediate Similarity	NPC188879
0.8406	Intermediate Similarity	NPC254841
0.8406	Intermediate Similarity	NPC73078
0.8406	Intermediate Similarity	NPC250266
0.8406	Intermediate Similarity	NPC319870
0.8406	Intermediate Similarity	NPC148738
0.8406	Intermediate Similarity	NPC266597
0.8406	Intermediate Similarity	NPC327612
0.8394	Intermediate Similarity	NPC223616
0.8394	Intermediate Similarity	NPC60667
0.8382	Intermediate Similarity	NPC108113
0.8382	Intermediate Similarity	NPC18877
0.8382	Intermediate Similarity	NPC20560
0.8382	Intermediate Similarity	NPC82225
0.8382	Intermediate Similarity	NPC93756
0.8382	Intermediate Similarity	NPC223457
0.8382	Intermediate Similarity	NPC294593
0.8382	Intermediate Similarity	NPC204960
0.8382	Intermediate Similarity	NPC144051
0.8382	Intermediate Similarity	NPC27643
0.8382	Intermediate Similarity	NPC28753
0.8382	Intermediate Similarity	NPC159623
0.838	Intermediate Similarity	NPC273538
0.838	Intermediate Similarity	NPC216538
0.837	Intermediate Similarity	NPC113006
0.8369	Intermediate Similarity	NPC473042
0.8369	Intermediate Similarity	NPC204469
0.8369	Intermediate Similarity	NPC200694
0.8358	Intermediate Similarity	NPC469929
0.8357	Intermediate Similarity	NPC284550
0.8357	Intermediate Similarity	NPC241100
0.8357	Intermediate Similarity	NPC159275
0.8357	Intermediate Similarity	NPC471587
0.8357	Intermediate Similarity	NPC129853
0.8357	Intermediate Similarity	NPC188243
0.8357	Intermediate Similarity	NPC6407
0.8357	Intermediate Similarity	NPC110228
0.8357	Intermediate Similarity	NPC76445
0.8345	Intermediate Similarity	NPC280284
0.8345	Intermediate Similarity	NPC118813
0.8345	Intermediate Similarity	NPC99333
0.8345	Intermediate Similarity	NPC470669
0.8345	Intermediate Similarity	NPC131130
0.8345	Intermediate Similarity	NPC276905
0.8345	Intermediate Similarity	NPC188947
0.8345	Intermediate Similarity	NPC470668
0.8345	Intermediate Similarity	NPC201395
0.8333	Intermediate Similarity	NPC156910
0.8333	Intermediate Similarity	NPC116775
0.8333	Intermediate Similarity	NPC240593
0.8333	Intermediate Similarity	NPC281917
0.8333	Intermediate Similarity	NPC470397
0.8333	Intermediate Similarity	NPC470398
0.8333	Intermediate Similarity	NPC13408
0.8333	Intermediate Similarity	NPC187432
0.8333	Intermediate Similarity	NPC256042
0.8333	Intermediate Similarity	NPC216361
0.8322	Intermediate Similarity	NPC124729
0.8322	Intermediate Similarity	NPC99454
0.8322	Intermediate Similarity	NPC130176
0.8322	Intermediate Similarity	NPC470458
0.8321	Intermediate Similarity	NPC286336
0.831	Intermediate Similarity	NPC212932
0.831	Intermediate Similarity	NPC190637
0.831	Intermediate Similarity	NPC473812
0.831	Intermediate Similarity	NPC24821
0.831	Intermediate Similarity	NPC473813
0.831	Intermediate Similarity	NPC293053
0.831	Intermediate Similarity	NPC9117
0.8309	Intermediate Similarity	NPC129132
0.8309	Intermediate Similarity	NPC212631
0.8309	Intermediate Similarity	NPC87231
0.8309	Intermediate Similarity	NPC257756
0.8309	Intermediate Similarity	NPC205468
0.8298	Intermediate Similarity	NPC282300
0.8298	Intermediate Similarity	NPC324386
0.8298	Intermediate Similarity	NPC229916
0.8298	Intermediate Similarity	NPC312391
0.8298	Intermediate Similarity	NPC4743
0.8298	Intermediate Similarity	NPC213322
0.8298	Intermediate Similarity	NPC3188
0.8298	Intermediate Similarity	NPC310128
0.8298	Intermediate Similarity	NPC110969
0.8286	Intermediate Similarity	NPC53181
0.8286	Intermediate Similarity	NPC216978
0.8286	Intermediate Similarity	NPC96565
0.8286	Intermediate Similarity	NPC139554
0.8286	Intermediate Similarity	NPC140890
0.8286	Intermediate Similarity	NPC301217
0.8286	Intermediate Similarity	NPC310370
0.8286	Intermediate Similarity	NPC261234
0.8286	Intermediate Similarity	NPC220062
0.8286	Intermediate Similarity	NPC183642
0.8286	Intermediate Similarity	NPC217186
0.8286	Intermediate Similarity	NPC55018
0.8286	Intermediate Similarity	NPC170812
0.8286	Intermediate Similarity	NPC303633
0.8284	Intermediate Similarity	NPC69235
0.8284	Intermediate Similarity	NPC212379
0.8276	Intermediate Similarity	NPC470461
0.8276	Intermediate Similarity	NPC477941
0.8273	Intermediate Similarity	NPC79943
0.8273	Intermediate Similarity	NPC295261
0.8273	Intermediate Similarity	NPC107586
0.8273	Intermediate Similarity	NPC275055
0.8273	Intermediate Similarity	NPC32441
0.8273	Intermediate Similarity	NPC332594
0.8273	Intermediate Similarity	NPC287246
0.8273	Intermediate Similarity	NPC12296
0.8273	Intermediate Similarity	NPC290291
0.8273	Intermediate Similarity	NPC228661
0.8273	Intermediate Similarity	NPC296490
0.8273	Intermediate Similarity	NPC299379

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 NPC146615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	942
0.2-0.3	1546
0.3-0.4	2622
0.4-0.5	1900
0.5-0.6	1235
0.6-0.7	505
0.7-0.8	114
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.838	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1240	Approved
0.8231	Intermediate Similarity	NPD422	Phase 1
0.8227	Intermediate Similarity	NPD3750	Approved
0.8222	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1549	Phase 2
0.8116	Intermediate Similarity	NPD1607	Approved
0.8099	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7985	Intermediate Similarity	NPD2797	Approved
0.7956	Intermediate Similarity	NPD1296	Phase 2
0.7956	Intermediate Similarity	NPD3268	Approved
0.7943	Intermediate Similarity	NPD6099	Approved
0.7943	Intermediate Similarity	NPD1551	Phase 2
0.7943	Intermediate Similarity	NPD6100	Approved
0.7923	Intermediate Similarity	NPD1548	Phase 1
0.7895	Intermediate Similarity	NPD7075	Discontinued
0.7891	Intermediate Similarity	NPD5403	Approved
0.7877	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD5401	Approved
0.7872	Intermediate Similarity	NPD3748	Approved
0.7852	Intermediate Similarity	NPD6599	Discontinued
0.7836	Intermediate Similarity	NPD4749	Approved
0.7829	Intermediate Similarity	NPD3882	Suspended
0.7823	Intermediate Similarity	NPD1512	Approved
0.782	Intermediate Similarity	NPD1610	Phase 2
0.7817	Intermediate Similarity	NPD2796	Approved
0.7815	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1241	Discontinued
0.781	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD3225	Approved
0.7761	Intermediate Similarity	NPD9717	Approved
0.7748	Intermediate Similarity	NPD6801	Discontinued
0.7748	Intermediate Similarity	NPD1934	Approved
0.7721	Intermediate Similarity	NPD3267	Approved
0.7721	Intermediate Similarity	NPD1203	Approved
0.7721	Intermediate Similarity	NPD3266	Approved
0.7708	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD6798	Discontinued
0.7697	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1511	Approved
0.7682	Intermediate Similarity	NPD7411	Suspended
0.7655	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6651	Approved
0.7582	Intermediate Similarity	NPD2801	Approved
0.7571	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6355	Discontinued
0.7535	Intermediate Similarity	NPD5124	Phase 1
0.7535	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5402	Approved
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7768	Phase 2
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7481	Intermediate Similarity	NPD3496	Discontinued
0.7468	Intermediate Similarity	NPD7819	Suspended
0.7453	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6832	Phase 2
0.7426	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6233	Phase 2
0.7379	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD9493	Approved
0.7357	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1613	Approved
0.7343	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.7325	Intermediate Similarity	NPD3749	Approved
0.7324	Intermediate Similarity	NPD2313	Discontinued
0.7299	Intermediate Similarity	NPD1535	Discovery
0.7297	Intermediate Similarity	NPD1243	Approved
0.7293	Intermediate Similarity	NPD6671	Approved
0.7286	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2344	Approved
0.7279	Intermediate Similarity	NPD6004	Phase 3
0.7279	Intermediate Similarity	NPD1778	Approved
0.7279	Intermediate Similarity	NPD17	Approved
0.7279	Intermediate Similarity	NPD6005	Phase 3
0.7279	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6002	Phase 3
0.7279	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4062	Phase 3
0.7267	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9545	Approved
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.7256	Intermediate Similarity	NPD6797	Phase 2
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7246	Intermediate Similarity	NPD1481	Phase 2
0.7222	Intermediate Similarity	NPD846	Approved
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7222	Intermediate Similarity	NPD940	Approved
0.7222	Intermediate Similarity	NPD4307	Phase 2
0.7212	Intermediate Similarity	NPD7251	Discontinued
0.7209	Intermediate Similarity	NPD290	Approved
0.7203	Intermediate Similarity	NPD411	Approved
0.7197	Intermediate Similarity	NPD4288	Approved
0.719	Intermediate Similarity	NPD920	Approved
0.7188	Intermediate Similarity	NPD6959	Discontinued
0.7181	Intermediate Similarity	NPD1652	Phase 2
0.7178	Intermediate Similarity	NPD3751	Discontinued
0.7174	Intermediate Similarity	NPD1091	Approved
0.7172	Intermediate Similarity	NPD447	Suspended
0.7171	Intermediate Similarity	NPD2534	Approved
0.7171	Intermediate Similarity	NPD2533	Approved
0.7171	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2532	Approved
0.717	Intermediate Similarity	NPD919	Approved
0.7169	Intermediate Similarity	NPD7808	Phase 3
0.7163	Intermediate Similarity	NPD2798	Approved
0.7163	Intermediate Similarity	NPD1019	Discontinued
0.7152	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3027	Phase 3
0.7132	Intermediate Similarity	NPD968	Approved
0.7114	Intermediate Similarity	NPD2424	Discontinued
0.7099	Intermediate Similarity	NPD4750	Phase 3
0.7099	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3226	Approved
0.7091	Intermediate Similarity	NPD7074	Phase 3
0.7086	Intermediate Similarity	NPD2354	Approved
0.7086	Intermediate Similarity	NPD2309	Approved
0.7081	Intermediate Similarity	NPD1247	Approved
0.7073	Intermediate Similarity	NPD3818	Discontinued
0.7067	Intermediate Similarity	NPD2654	Approved
0.7066	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4340	Discontinued
0.7055	Intermediate Similarity	NPD1933	Approved
0.7055	Intermediate Similarity	NPD230	Phase 1
0.7055	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD9697	Approved
0.7048	Intermediate Similarity	NPD5953	Discontinued
0.7047	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2346	Discontinued
0.703	Intermediate Similarity	NPD7286	Phase 2
0.703	Intermediate Similarity	NPD7054	Approved
0.7023	Intermediate Similarity	NPD2684	Approved
0.7014	Intermediate Similarity	NPD7095	Approved
0.7013	Intermediate Similarity	NPD5049	Phase 3
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD3972	Approved
0.6994	Remote Similarity	NPD3926	Phase 2
0.6993	Remote Similarity	NPD7213	Phase 3
0.6993	Remote Similarity	NPD7212	Phase 2
0.6993	Remote Similarity	NPD2861	Phase 2
0.6988	Remote Similarity	NPD7472	Approved
0.6986	Remote Similarity	NPD943	Approved
0.698	Remote Similarity	NPD4477	Approved
0.698	Remote Similarity	NPD4476	Approved
0.6978	Remote Similarity	NPD3847	Discontinued
0.6966	Remote Similarity	NPD3764	Approved
0.6966	Remote Similarity	NPD1048	Approved
0.6964	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2403	Approved
0.6951	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7447	Phase 1
0.694	Remote Similarity	NPD5535	Approved
0.694	Remote Similarity	NPD7843	Approved
0.6933	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3787	Discontinued
0.6933	Remote Similarity	NPD2353	Approved
0.6933	Remote Similarity	NPD5763	Approved
0.6933	Remote Similarity	NPD5762	Approved
0.6933	Remote Similarity	NPD6232	Discontinued
0.6928	Remote Similarity	NPD5844	Phase 1
0.6923	Remote Similarity	NPD5647	Approved
0.6918	Remote Similarity	NPD1465	Phase 2
0.6914	Remote Similarity	NPD5494	Approved
0.6913	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7473	Discontinued
0.6906	Remote Similarity	NPD4626	Approved
0.6901	Remote Similarity	NPD8651	Approved
0.6901	Remote Similarity	NPD1876	Approved
0.6894	Remote Similarity	NPD6971	Discontinued
0.6887	Remote Similarity	NPD4534	Discontinued
0.6883	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7199	Phase 2
0.6867	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3887	Approved
0.6859	Remote Similarity	NPD6980	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