NPASS Compound

Structure

CID201419 OpenBabel06191715592D 21 23 0 0 0 0 0 0 0 0999 V2000 3.0988 1.3552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5299 0.3795 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 0.9749 -2.0245 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 2.5355 0.5290 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 -2.5139 -1.6235 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 -0.6235 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 2.4060 -1.1982 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 0.9749 -0.2225 0.0000 C 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 1.1044 1.5047 0.0000 O 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 3.9665 -0.4467 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 5 1 0 0 0 0 3 9 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 9 2 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 12 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 16 2 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:	3.817
LogD:	3.043
LogS:	-3.643
# 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:	2.983
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.969
MDCK Permeability:	1.7659185687080026e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	100.00225830078125%
Volume Distribution (VD):	0.412
Pgp-substrate:	2.3683879375457764%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.204
CYP2C19-substrate:	0.405
CYP2C9-inhibitor:	0.348
CYP2C9-substrate:	0.888
CYP2D6-inhibitor:	0.433
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	10.487
Half-life (T1/2):	0.808

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.436
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.974
Maximum Recommended Daily Dose:	0.847
Skin Sensitization:	0.958
Carcinogencity:	0.482
Eye Corrosion:	0.004
Eye Irritation:	0.918
Respiratory Toxicity:	0.644

Download Data

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

Natural Product: NPC201419

Natural Product ID:	NPC201419
*Common Name:**	Bauhinoxepin I
IUPAC Name:	8-hydroxy-3-methoxy-2-methyl-5,6-dihydrobenzo[b][1]benzoxepine-1,4-dione
Synonyms:	bauhinoxepin I
Standard InCHIKey:	ATBQBNKWWGOEFJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-8-13(18)16-11(14(19)15(8)20-2)5-3-9-7-10(17)4-6-12(9)21-16/h4,6-7,17H,3,5H2,1-2H3
SMILES:	COC1=C(C)C(=O)C2=C(C1=O)CCc1c(O2)ccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389398
PubChem CID:	16679966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-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]
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]
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]

☑ 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
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	>	34900.0	nM	PMID[452723]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	10100.0	nM	PMID[452723]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	38800.0	nM	PMID[452723]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	174800.0	nM	PMID[452723]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10500.0	nM	PMID[452723]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	174800.0	nM	PMID[452723]
NPT27	Others	Unspecified		IC50	=	41900.0	nM	PMID[452723]

☑ 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 NPC201419 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	287
0.1-0.2	1483
0.2-0.3	4078
0.3-0.4	10115
0.4-0.5	8283
0.5-0.6	4460
0.6-0.7	9761
0.7-0.8	4111
0.8-0.85	79
0.85-0.9	39
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8934	High Similarity	NPC152159
0.8915	High Similarity	NPC146615
0.873	High Similarity	NPC49441
0.8702	High Similarity	NPC474246
0.8702	High Similarity	NPC474143
0.8692	High Similarity	NPC59654
0.8682	High Similarity	NPC477212
0.8682	High Similarity	NPC477214
0.8682	High Similarity	NPC477211
0.8682	High Similarity	NPC319422
0.8647	High Similarity	NPC477210
0.8626	High Similarity	NPC475880
0.8571	High Similarity	NPC470871
0.855	High Similarity	NPC271832
0.8527	High Similarity	NPC477213
0.8489	Intermediate Similarity	NPC316691
0.845	Intermediate Similarity	NPC98509
0.8429	Intermediate Similarity	NPC471600
0.8421	Intermediate Similarity	NPC141549
0.8406	Intermediate Similarity	NPC475063
0.8406	Intermediate Similarity	NPC475044
0.8397	Intermediate Similarity	NPC95034
0.8397	Intermediate Similarity	NPC142087
0.8394	Intermediate Similarity	NPC475005
0.8394	Intermediate Similarity	NPC474943
0.8382	Intermediate Similarity	NPC194847
0.8382	Intermediate Similarity	NPC21797
0.8359	Intermediate Similarity	NPC476165
0.8358	Intermediate Similarity	NPC118253
0.8358	Intermediate Similarity	NPC251549
0.8346	Intermediate Similarity	NPC278787
0.8346	Intermediate Similarity	NPC196621
0.8346	Intermediate Similarity	NPC172673
0.8346	Intermediate Similarity	NPC7569
0.8333	Intermediate Similarity	NPC475045
0.8309	Intermediate Similarity	NPC281513
0.8309	Intermediate Similarity	NPC22222
0.8308	Intermediate Similarity	NPC276962
0.8308	Intermediate Similarity	NPC190086
0.8308	Intermediate Similarity	NPC147896
0.8286	Intermediate Similarity	NPC474154
0.8261	Intermediate Similarity	NPC475028
0.8261	Intermediate Similarity	NPC476025
0.8248	Intermediate Similarity	NPC64157
0.8248	Intermediate Similarity	NPC278832
0.8248	Intermediate Similarity	NPC266245
0.8244	Intermediate Similarity	NPC224657
0.8235	Intermediate Similarity	NPC265793
0.8222	Intermediate Similarity	NPC329427
0.8222	Intermediate Similarity	NPC317601
0.8222	Intermediate Similarity	NPC239302
0.8188	Intermediate Similarity	NPC130976
0.8188	Intermediate Similarity	NPC477534
0.8175	Intermediate Similarity	NPC325646
0.8175	Intermediate Similarity	NPC28951
0.8169	Intermediate Similarity	NPC477409
0.8168	Intermediate Similarity	NPC474237
0.8162	Intermediate Similarity	NPC477536
0.816	Intermediate Similarity	NPC114144
0.8148	Intermediate Similarity	NPC324488
0.8145	Intermediate Similarity	NPC474920
0.8143	Intermediate Similarity	NPC477537
0.8143	Intermediate Similarity	NPC477535
0.8125	Intermediate Similarity	NPC51341
0.812	Intermediate Similarity	NPC298884
0.8116	Intermediate Similarity	NPC472881
0.8102	Intermediate Similarity	NPC27394
0.8095	Intermediate Similarity	NPC473718
0.8092	Intermediate Similarity	NPC248786
0.8092	Intermediate Similarity	NPC135062
0.8088	Intermediate Similarity	NPC312560
0.8085	Intermediate Similarity	NPC145673
0.8071	Intermediate Similarity	NPC268691
0.8071	Intermediate Similarity	NPC475012
0.8071	Intermediate Similarity	NPC477408
0.8062	Intermediate Similarity	NPC474874
0.8062	Intermediate Similarity	NPC14177
0.806	Intermediate Similarity	NPC226661
0.8043	Intermediate Similarity	NPC475011
0.8033	Intermediate Similarity	NPC233320
0.8031	Intermediate Similarity	NPC19290
0.8031	Intermediate Similarity	NPC163398
0.8031	Intermediate Similarity	NPC69539
0.803	Intermediate Similarity	NPC4012
0.8028	Intermediate Similarity	NPC329493
0.8015	Intermediate Similarity	NPC302211
0.8015	Intermediate Similarity	NPC205360
0.8	Intermediate Similarity	NPC98395
0.8	Intermediate Similarity	NPC206028
0.7986	Intermediate Similarity	NPC474610
0.7985	Intermediate Similarity	NPC71525
0.7984	Intermediate Similarity	NPC32152
0.7984	Intermediate Similarity	NPC471449
0.7969	Intermediate Similarity	NPC238176
0.7969	Intermediate Similarity	NPC187993
0.7958	Intermediate Similarity	NPC472335
0.7958	Intermediate Similarity	NPC472332
0.7955	Intermediate Similarity	NPC93730
0.7953	Intermediate Similarity	NPC301321
0.7945	Intermediate Similarity	NPC474556
0.7943	Intermediate Similarity	NPC18457
0.7943	Intermediate Similarity	NPC322021
0.7941	Intermediate Similarity	NPC253488
0.7929	Intermediate Similarity	NPC309452
0.7923	Intermediate Similarity	NPC474131
0.7923	Intermediate Similarity	NPC232295
0.792	Intermediate Similarity	NPC275627
0.7917	Intermediate Similarity	NPC89664
0.7917	Intermediate Similarity	NPC274085
0.7914	Intermediate Similarity	NPC476018
0.7914	Intermediate Similarity	NPC291119
0.7914	Intermediate Similarity	NPC475029
0.7914	Intermediate Similarity	NPC281169
0.7914	Intermediate Similarity	NPC22644
0.791	Intermediate Similarity	NPC84076
0.791	Intermediate Similarity	NPC303680
0.791	Intermediate Similarity	NPC90128
0.791	Intermediate Similarity	NPC51037
0.7907	Intermediate Similarity	NPC283616
0.7895	Intermediate Similarity	NPC474766
0.7895	Intermediate Similarity	NPC89630
0.7891	Intermediate Similarity	NPC154256
0.7891	Intermediate Similarity	NPC290470
0.7883	Intermediate Similarity	NPC258073
0.7879	Intermediate Similarity	NPC164947
0.7879	Intermediate Similarity	NPC132518
0.7879	Intermediate Similarity	NPC204535
0.7879	Intermediate Similarity	NPC477151
0.7879	Intermediate Similarity	NPC46586
0.7874	Intermediate Similarity	NPC87563
0.7872	Intermediate Similarity	NPC475104
0.7868	Intermediate Similarity	NPC304622
0.7863	Intermediate Similarity	NPC473875
0.7857	Intermediate Similarity	NPC232996
0.7852	Intermediate Similarity	NPC123722
0.7852	Intermediate Similarity	NPC123228
0.7852	Intermediate Similarity	NPC45537
0.7852	Intermediate Similarity	NPC151167
0.7852	Intermediate Similarity	NPC276466
0.7852	Intermediate Similarity	NPC470841
0.7852	Intermediate Similarity	NPC5018
0.7846	Intermediate Similarity	NPC98748
0.784	Intermediate Similarity	NPC208229
0.7838	Intermediate Similarity	NPC475717
0.7838	Intermediate Similarity	NPC475718
0.7836	Intermediate Similarity	NPC3221
0.7836	Intermediate Similarity	NPC287473
0.7836	Intermediate Similarity	NPC257589
0.7836	Intermediate Similarity	NPC53305
0.7832	Intermediate Similarity	NPC146679
0.7832	Intermediate Similarity	NPC59951
0.7832	Intermediate Similarity	NPC230285
0.7832	Intermediate Similarity	NPC124365
0.7832	Intermediate Similarity	NPC184536
0.7832	Intermediate Similarity	NPC103342
0.7832	Intermediate Similarity	NPC103904
0.7829	Intermediate Similarity	NPC240664
0.7826	Intermediate Similarity	NPC472882
0.7826	Intermediate Similarity	NPC119985
0.7826	Intermediate Similarity	NPC477406
0.7826	Intermediate Similarity	NPC280476
0.7823	Intermediate Similarity	NPC68260
0.7823	Intermediate Similarity	NPC279887
0.7823	Intermediate Similarity	NPC5537
0.782	Intermediate Similarity	NPC4181
0.782	Intermediate Similarity	NPC164778
0.782	Intermediate Similarity	NPC163083
0.782	Intermediate Similarity	NPC477152
0.782	Intermediate Similarity	NPC474130
0.782	Intermediate Similarity	NPC257976
0.782	Intermediate Similarity	NPC242372
0.7817	Intermediate Similarity	NPC79372
0.7817	Intermediate Similarity	NPC76312
0.781	Intermediate Similarity	NPC2989
0.781	Intermediate Similarity	NPC470725
0.7808	Intermediate Similarity	NPC178343
0.7808	Intermediate Similarity	NPC5820
0.7808	Intermediate Similarity	NPC306488
0.7808	Intermediate Similarity	NPC130176
0.7808	Intermediate Similarity	NPC308799
0.7808	Intermediate Similarity	NPC99454
0.7803	Intermediate Similarity	NPC201777
0.7801	Intermediate Similarity	NPC284184
0.7801	Intermediate Similarity	NPC301341
0.78	Intermediate Similarity	NPC84721
0.7795	Intermediate Similarity	NPC28784
0.7795	Intermediate Similarity	NPC296144
0.7794	Intermediate Similarity	NPC237225
0.7794	Intermediate Similarity	NPC81261
0.7793	Intermediate Similarity	NPC232883
0.7793	Intermediate Similarity	NPC469642
0.7786	Intermediate Similarity	NPC193193
0.7786	Intermediate Similarity	NPC51087
0.7786	Intermediate Similarity	NPC161856
0.7786	Intermediate Similarity	NPC31314
0.7786	Intermediate Similarity	NPC168050
0.7778	Intermediate Similarity	NPC262094
0.7778	Intermediate Similarity	NPC92207
0.7778	Intermediate Similarity	NPC201297
0.7778	Intermediate Similarity	NPC136840

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 NPC201419 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	969
0.2-0.3	1470
0.3-0.4	2492
0.4-0.5	1985
0.5-0.6	1245
0.6-0.7	597
0.7-0.8	116
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8425	Intermediate Similarity	NPD3496	Discontinued
0.824	Intermediate Similarity	NPD6671	Approved
0.7937	Intermediate Similarity	NPD1241	Discontinued
0.7929	Intermediate Similarity	NPD2935	Discontinued
0.7836	Intermediate Similarity	NPD2797	Approved
0.781	Intermediate Similarity	NPD3268	Approved
0.781	Intermediate Similarity	NPD6798	Discontinued
0.7803	Intermediate Similarity	NPD1535	Discovery
0.777	Intermediate Similarity	NPD6355	Discontinued
0.7754	Intermediate Similarity	NPD6233	Phase 2
0.7744	Intermediate Similarity	NPD1481	Phase 2
0.774	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD4060	Phase 1
0.7681	Intermediate Similarity	NPD2313	Discontinued
0.7661	Intermediate Similarity	NPD968	Approved
0.7622	Intermediate Similarity	NPD2346	Discontinued
0.7612	Intermediate Similarity	NPD1608	Approved
0.7612	Intermediate Similarity	NPD9717	Approved
0.7606	Intermediate Similarity	NPD2799	Discontinued
0.7586	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3267	Approved
0.7574	Intermediate Similarity	NPD3266	Approved
0.7574	Intermediate Similarity	NPD1203	Approved
0.7537	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1778	Approved
0.7518	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD4308	Phase 3
0.7482	Intermediate Similarity	NPD7095	Approved
0.7466	Intermediate Similarity	NPD3750	Approved
0.7464	Intermediate Similarity	NPD2861	Phase 2
0.7451	Intermediate Similarity	NPD2801	Approved
0.745	Intermediate Similarity	NPD1512	Approved
0.7431	Intermediate Similarity	NPD6100	Approved
0.7431	Intermediate Similarity	NPD6099	Approved
0.7429	Intermediate Similarity	NPD411	Approved
0.7426	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1611	Approved
0.7403	Intermediate Similarity	NPD5402	Approved
0.7397	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2798	Approved
0.7388	Intermediate Similarity	NPD17	Approved
0.7388	Intermediate Similarity	NPD4626	Approved
0.7386	Intermediate Similarity	NPD1934	Approved
0.7379	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4062	Phase 3
0.7372	Intermediate Similarity	NPD3225	Approved
0.7368	Intermediate Similarity	NPD1894	Discontinued
0.7355	Intermediate Similarity	NPD3882	Suspended
0.7351	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1549	Phase 2
0.7324	Intermediate Similarity	NPD1240	Approved
0.7315	Intermediate Similarity	NPD1511	Approved
0.7313	Intermediate Similarity	NPD5585	Approved
0.7313	Intermediate Similarity	NPD1651	Approved
0.7305	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3226	Approved
0.7299	Intermediate Similarity	NPD4749	Approved
0.7297	Intermediate Similarity	NPD2309	Approved
0.7286	Intermediate Similarity	NPD6832	Phase 2
0.7279	Intermediate Similarity	NPD422	Phase 1
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7258	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1398	Phase 1
0.7246	Intermediate Similarity	NPD6696	Suspended
0.7246	Intermediate Similarity	NPD1283	Approved
0.7241	Intermediate Similarity	NPD1510	Phase 2
0.7222	Intermediate Similarity	NPD1607	Approved
0.7218	Intermediate Similarity	NPD7340	Approved
0.7218	Intermediate Similarity	NPD9493	Approved
0.7218	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2424	Discontinued
0.7203	Intermediate Similarity	NPD4307	Phase 2
0.72	Intermediate Similarity	NPD6799	Approved
0.7197	Intermediate Similarity	NPD7075	Discontinued
0.7192	Intermediate Similarity	NPD4477	Approved
0.7192	Intermediate Similarity	NPD6032	Approved
0.7192	Intermediate Similarity	NPD1551	Phase 2
0.7192	Intermediate Similarity	NPD4476	Approved
0.7188	Intermediate Similarity	NPD290	Approved
0.7185	Intermediate Similarity	NPD5691	Approved
0.7181	Intermediate Similarity	NPD2354	Approved
0.7179	Intermediate Similarity	NPD3817	Phase 2
0.7174	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD9697	Approved
0.7164	Intermediate Similarity	NPD5536	Phase 2
0.7162	Intermediate Similarity	NPD2800	Approved
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7132	Intermediate Similarity	NPD2684	Approved
0.7123	Intermediate Similarity	NPD7033	Discontinued
0.7123	Intermediate Similarity	NPD3748	Approved
0.7122	Intermediate Similarity	NPD1876	Approved
0.7115	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4628	Phase 3
0.7105	Intermediate Similarity	NPD5049	Phase 3
0.7103	Intermediate Similarity	NPD6653	Approved
0.7101	Intermediate Similarity	NPD3972	Approved
0.7099	Intermediate Similarity	NPD228	Approved
0.7095	Intermediate Similarity	NPD4534	Discontinued
0.7092	Intermediate Similarity	NPD9494	Approved
0.708	Intermediate Similarity	NPD3847	Discontinued
0.7078	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2796	Approved
0.7068	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1296	Phase 2
0.7063	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5403	Approved
0.7055	Intermediate Similarity	NPD3751	Discontinued
0.705	Intermediate Similarity	NPD4359	Approved
0.7045	Intermediate Similarity	NPD5535	Approved
0.7045	Intermediate Similarity	NPD7843	Approved
0.7042	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4908	Phase 1
0.7042	Intermediate Similarity	NPD2614	Approved
0.7039	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5401	Approved
0.7032	Intermediate Similarity	NPD6599	Discontinued
0.7029	Intermediate Similarity	NPD1281	Approved
0.7029	Intermediate Similarity	NPD1201	Approved
0.7029	Intermediate Similarity	NPD1610	Phase 2
0.7027	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2353	Approved
0.7021	Intermediate Similarity	NPD5647	Approved
0.7021	Intermediate Similarity	NPD6584	Phase 3
0.7015	Intermediate Similarity	NPD7157	Approved
0.7014	Intermediate Similarity	NPD8032	Phase 2
0.7007	Intermediate Similarity	NPD2932	Approved
0.7006	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4110	Phase 3
0.6993	Remote Similarity	NPD4625	Phase 3
0.6985	Remote Similarity	NPD1548	Phase 1
0.6985	Remote Similarity	NPD9545	Approved
0.698	Remote Similarity	NPD2897	Discontinued
0.698	Remote Similarity	NPD5958	Discontinued
0.6978	Remote Similarity	NPD2230	Approved
0.6978	Remote Similarity	NPD2233	Approved
0.6978	Remote Similarity	NPD2231	Phase 2
0.6978	Remote Similarity	NPD2232	Approved
0.6978	Remote Similarity	NPD2235	Phase 2
0.6974	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2237	Approved
0.6966	Remote Similarity	NPD1613	Approved
0.6966	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2979	Phase 3
0.6962	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1519	Approved
0.6959	Remote Similarity	NPD1538	Phase 1
0.6959	Remote Similarity	NPD1537	Approved
0.6957	Remote Similarity	NPD1247	Approved
0.6954	Remote Similarity	NPD3887	Approved
0.695	Remote Similarity	NPD987	Approved
0.695	Remote Similarity	NPD1470	Approved
0.6946	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6801	Discontinued
0.6935	Remote Similarity	NPD844	Approved
0.6928	Remote Similarity	NPD6797	Phase 2
0.6923	Remote Similarity	NPD4380	Phase 2
0.6918	Remote Similarity	NPD4622	Approved
0.6918	Remote Similarity	NPD1933	Approved
0.6918	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4618	Approved
0.6909	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7003	Approved
0.6887	Remote Similarity	NPD8166	Discontinued
0.6886	Remote Similarity	NPD7251	Discontinued
0.6884	Remote Similarity	NPD3019	Approved
0.6883	Remote Similarity	NPD6273	Approved
0.688	Remote Similarity	NPD288	Approved
0.6879	Remote Similarity	NPD7411	Suspended
0.6875	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5283	Phase 1
0.686	Remote Similarity	NPD9295	Approved
0.6859	Remote Similarity	NPD2651	Approved
0.6859	Remote Similarity	NPD2649	Approved
0.6859	Remote Similarity	NPD3769	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data