NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.05
Volume:	250.527
LogP:	1.918
LogD:	2.095
LogS:	-3.486
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.629
Synthetic Accessibility Score:	2.522
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.712
MDCK Permeability:	9.704343028715812e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	94.40180206298828%
Volume Distribution (VD):	0.694
Pgp-substrate:	3.4062414169311523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.454
CYP2C9-substrate:	0.749
CYP2D6-inhibitor:	0.648
CYP2D6-substrate:	0.676
CYP3A4-inhibitor:	0.711
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	18.603
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.096
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.745
Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.119
Skin Sensitization:	0.895
Carcinogencity:	0.456
Eye Corrosion:	0.01
Eye Irritation:	0.934
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC28103

Natural Product ID:	NPC28103
*Common Name:**	Caesalpiniaphenol C
IUPAC Name:	3,9,10-trihydroxybenzo[d][1]benzoxepin-7-one
Synonyms:	Caesalpiniaphenol C
Standard InCHIKey:	ZAOGOJVQXXXNAU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O5/c15-7-1-2-8-9-4-11(16)12(17)5-10(9)13(18)6-19-14(8)3-7/h1-5,15-17H,6H2
SMILES:	c1cc2-c3cc(c(cc3C(=O)COc2cc1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208385
PubChem CID:	71452598
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001910] Benzoxepines

*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
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[19420770]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800859]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23127886]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23234407]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	seeds	Nanning, Guangxi Province, China	2013-APR	PMID[26398312]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29935	Caesalpinia sappan	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[468990]
NPT35	Others	n.a.		IC50	=	86250.0	nM	PMID[468990]

☑ 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 NPC28103 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	456
0.1-0.2	1943
0.2-0.3	4702
0.3-0.4	11304
0.4-0.5	6163
0.5-0.6	3480
0.6-0.7	5224
0.7-0.8	6615
0.8-0.85	2138
0.85-0.9	650
0.9-0.95	21
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.932	High Similarity	NPC223592
0.9195	High Similarity	NPC237904
0.9026	High Similarity	NPC153512
0.9	High Similarity	NPC86847
0.9	High Similarity	NPC140840
0.8961	High Similarity	NPC80534
0.8961	High Similarity	NPC56786
0.8947	High Similarity	NPC260582
0.894	High Similarity	NPC19545
0.8931	High Similarity	NPC477517
0.891	High Similarity	NPC104876
0.891	High Similarity	NPC245891
0.891	High Similarity	NPC55738
0.8903	High Similarity	NPC474638
0.8896	High Similarity	NPC141212
0.8896	High Similarity	NPC246328
0.8896	High Similarity	NPC256346
0.8896	High Similarity	NPC27532
0.8896	High Similarity	NPC325028
0.8889	High Similarity	NPC260895
0.8889	High Similarity	NPC204350
0.8889	High Similarity	NPC78505
0.8882	High Similarity	NPC183959
0.8882	High Similarity	NPC105512
0.8882	High Similarity	NPC1612
0.8874	High Similarity	NPC74881
0.8874	High Similarity	NPC51443
0.8874	High Similarity	NPC95864
0.8859	High Similarity	NPC287722
0.8839	High Similarity	NPC67396
0.8831	High Similarity	NPC36835
0.8831	High Similarity	NPC61506
0.8831	High Similarity	NPC260491
0.8831	High Similarity	NPC304954
0.8831	High Similarity	NPC9743
0.8831	High Similarity	NPC240476
0.8831	High Similarity	NPC246162
0.8824	High Similarity	NPC29231
0.8824	High Similarity	NPC188871
0.8824	High Similarity	NPC151473
0.8824	High Similarity	NPC149127
0.8824	High Similarity	NPC85131
0.8824	High Similarity	NPC286342
0.8816	High Similarity	NPC321011
0.8816	High Similarity	NPC3036
0.8816	High Similarity	NPC196277
0.8816	High Similarity	NPC188679
0.8816	High Similarity	NPC294852
0.8816	High Similarity	NPC43669
0.8816	High Similarity	NPC272721
0.8808	High Similarity	NPC179271
0.8808	High Similarity	NPC20791
0.8805	High Similarity	NPC263092
0.8805	High Similarity	NPC1755
0.8805	High Similarity	NPC1706
0.8805	High Similarity	NPC59295
0.8805	High Similarity	NPC39305
0.88	High Similarity	NPC207732
0.88	High Similarity	NPC38065
0.88	High Similarity	NPC242893
0.88	High Similarity	NPC105213
0.8792	High Similarity	NPC312256
0.8782	High Similarity	NPC24640
0.8782	High Similarity	NPC471500
0.8782	High Similarity	NPC472461
0.8782	High Similarity	NPC201837
0.8782	High Similarity	NPC265511
0.8774	High Similarity	NPC189130
0.8774	High Similarity	NPC281703
0.8774	High Similarity	NPC125487
0.8774	High Similarity	NPC469550
0.8766	High Similarity	NPC204515
0.8766	High Similarity	NPC230848
0.8766	High Similarity	NPC272566
0.8766	High Similarity	NPC31363
0.8766	High Similarity	NPC202157
0.8758	High Similarity	NPC270465
0.8758	High Similarity	NPC87125
0.8758	High Similarity	NPC195351
0.875	High Similarity	NPC125449
0.875	High Similarity	NPC77378
0.875	High Similarity	NPC168803
0.875	High Similarity	NPC188074
0.8742	High Similarity	NPC262282
0.8742	High Similarity	NPC238995
0.8742	High Similarity	NPC70136
0.8742	High Similarity	NPC272722
0.8734	High Similarity	NPC474960
0.8726	High Similarity	NPC52530
0.8726	High Similarity	NPC471515
0.8726	High Similarity	NPC273843
0.8726	High Similarity	NPC299520
0.8726	High Similarity	NPC471479
0.8726	High Similarity	NPC129684
0.8726	High Similarity	NPC472963
0.8726	High Similarity	NPC67876
0.8725	High Similarity	NPC110419
0.8718	High Similarity	NPC133392
0.8718	High Similarity	NPC214138
0.871	High Similarity	NPC257648
0.871	High Similarity	NPC82325
0.871	High Similarity	NPC55205
0.871	High Similarity	NPC19721
0.871	High Similarity	NPC477231
0.871	High Similarity	NPC260979
0.871	High Similarity	NPC279989
0.8704	High Similarity	NPC247136
0.8701	High Similarity	NPC62042
0.8701	High Similarity	NPC77858
0.8693	High Similarity	NPC12367
0.8693	High Similarity	NPC119059
0.8693	High Similarity	NPC218490
0.8693	High Similarity	NPC194856
0.8693	High Similarity	NPC118726
0.8693	High Similarity	NPC276930
0.8693	High Similarity	NPC107636
0.8684	High Similarity	NPC138978
0.8684	High Similarity	NPC169749
0.8679	High Similarity	NPC173137
0.8679	High Similarity	NPC308992
0.8675	High Similarity	NPC279121
0.8671	High Similarity	NPC210459
0.8671	High Similarity	NPC329091
0.8671	High Similarity	NPC195832
0.8671	High Similarity	NPC228501
0.8667	High Similarity	NPC103752
0.8667	High Similarity	NPC284556
0.8667	High Similarity	NPC301178
0.8662	High Similarity	NPC472907
0.8662	High Similarity	NPC326037
0.8662	High Similarity	NPC266960
0.8662	High Similarity	NPC475799
0.8662	High Similarity	NPC13779
0.8662	High Similarity	NPC13858
0.8662	High Similarity	NPC43243
0.8662	High Similarity	NPC320825
0.8662	High Similarity	NPC245546
0.8654	High Similarity	NPC179126
0.8654	High Similarity	NPC270620
0.8654	High Similarity	NPC271779
0.8654	High Similarity	NPC292214
0.8654	High Similarity	NPC472905
0.8654	High Similarity	NPC89474
0.8654	High Similarity	NPC236223
0.8654	High Similarity	NPC167091
0.8654	High Similarity	NPC78326
0.8654	High Similarity	NPC303950
0.8654	High Similarity	NPC88645
0.8654	High Similarity	NPC206238
0.8645	High Similarity	NPC251110
0.8645	High Similarity	NPC200740
0.8645	High Similarity	NPC125062
0.8645	High Similarity	NPC54394
0.8645	High Similarity	NPC225731
0.8645	High Similarity	NPC252933
0.8636	High Similarity	NPC40290
0.8636	High Similarity	NPC139293
0.8636	High Similarity	NPC200060
0.8636	High Similarity	NPC264289
0.8636	High Similarity	NPC69430
0.8636	High Similarity	NPC195763
0.8636	High Similarity	NPC80370
0.8636	High Similarity	NPC142876
0.8636	High Similarity	NPC333691
0.8636	High Similarity	NPC264550
0.8634	High Similarity	NPC45449
0.8634	High Similarity	NPC36320
0.8627	High Similarity	NPC275772
0.8627	High Similarity	NPC108406
0.8627	High Similarity	NPC77903
0.8627	High Similarity	NPC130230
0.8627	High Similarity	NPC17101
0.8627	High Similarity	NPC207729
0.8627	High Similarity	NPC239312
0.8627	High Similarity	NPC294972
0.8625	High Similarity	NPC472964
0.8625	High Similarity	NPC211107
0.8618	High Similarity	NPC131766
0.8618	High Similarity	NPC157133
0.8616	High Similarity	NPC321399
0.8616	High Similarity	NPC472902
0.8616	High Similarity	NPC470183
0.8616	High Similarity	NPC263449
0.8616	High Similarity	NPC200594
0.8616	High Similarity	NPC36217
0.8616	High Similarity	NPC471744
0.8609	High Similarity	NPC175013
0.8609	High Similarity	NPC471417
0.8608	High Similarity	NPC101830
0.8608	High Similarity	NPC136674
0.8608	High Similarity	NPC287979
0.8608	High Similarity	NPC110070
0.8608	High Similarity	NPC176665
0.8608	High Similarity	NPC99597
0.8608	High Similarity	NPC241904
0.8608	High Similarity	NPC163524
0.8608	High Similarity	NPC111969
0.8608	High Similarity	NPC203891
0.8608	High Similarity	NPC210084
0.8608	High Similarity	NPC300727

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 NPC28103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	437
0.1-0.2	1026
0.2-0.3	1756
0.3-0.4	2624
0.4-0.5	1684
0.5-0.6	1017
0.6-0.7	445
0.7-0.8	126
0.8-0.85	23
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8903	High Similarity	NPD3882	Suspended
0.8808	High Similarity	NPD1512	Approved
0.8675	High Similarity	NPD1511	Approved
0.859	High Similarity	NPD1934	Approved
0.8535	High Similarity	NPD2393	Clinical (unspecified phase)
0.8535	High Similarity	NPD1465	Phase 2
0.8428	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD2801	Approved
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8293	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6166	Phase 2
0.8293	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1510	Phase 2
0.8263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD3817	Phase 2
0.8243	Intermediate Similarity	NPD943	Approved
0.8235	Intermediate Similarity	NPD3750	Approved
0.8194	Intermediate Similarity	NPD6799	Approved
0.8193	Intermediate Similarity	NPD3818	Discontinued
0.8148	Intermediate Similarity	NPD7075	Discontinued
0.8141	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1240	Approved
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.8075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7819	Suspended
0.8067	Intermediate Similarity	NPD230	Phase 1
0.8059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD6797	Phase 2
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8013	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7988	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6232	Discontinued
0.7927	Intermediate Similarity	NPD3749	Approved
0.7917	Intermediate Similarity	NPD7473	Discontinued
0.7908	Intermediate Similarity	NPD3748	Approved
0.7904	Intermediate Similarity	NPD3926	Phase 2
0.7901	Intermediate Similarity	NPD6801	Discontinued
0.7888	Intermediate Similarity	NPD4380	Phase 2
0.7882	Intermediate Similarity	NPD7074	Phase 3
0.7881	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1613	Approved
0.787	Intermediate Similarity	NPD3751	Discontinued
0.7857	Intermediate Similarity	NPD2796	Approved
0.7852	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7808	Phase 3
0.7831	Intermediate Similarity	NPD5494	Approved
0.7824	Intermediate Similarity	NPD7054	Approved
0.7818	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5402	Approved
0.7798	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6959	Discontinued
0.7778	Intermediate Similarity	NPD7472	Approved
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7702	Intermediate Similarity	NPD5403	Approved
0.7697	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD9494	Approved
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7633	Intermediate Similarity	NPD3787	Discontinued
0.7632	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7411	Suspended
0.7616	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6190	Approved
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD2533	Approved
0.7578	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD2532	Approved
0.7574	Intermediate Similarity	NPD7199	Phase 2
0.7564	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7768	Phase 2
0.7544	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD920	Approved
0.7484	Intermediate Similarity	NPD2800	Approved
0.7469	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7451	Intermediate Similarity	NPD3027	Phase 3
0.745	Intermediate Similarity	NPD9269	Phase 2
0.7438	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7394	Intermediate Similarity	NPD3226	Approved
0.7391	Intermediate Similarity	NPD2309	Approved
0.7386	Intermediate Similarity	NPD6559	Discontinued
0.7375	Intermediate Similarity	NPD1243	Approved
0.7372	Intermediate Similarity	NPD447	Suspended
0.7358	Intermediate Similarity	NPD1471	Phase 3
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7333	Intermediate Similarity	NPD1608	Approved
0.7312	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1203	Approved
0.7296	Intermediate Similarity	NPD2935	Discontinued
0.7293	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3764	Approved
0.7289	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4288	Approved
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7262	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD6355	Discontinued
0.7256	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2346	Discontinued
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4966	Approved
0.7232	Intermediate Similarity	NPD5953	Discontinued
0.7229	Intermediate Similarity	NPD1653	Approved
0.7226	Intermediate Similarity	NPD4625	Phase 3
0.7225	Intermediate Similarity	NPD7229	Phase 3
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1470	Approved
0.7184	Intermediate Similarity	NPD5242	Approved
0.7181	Intermediate Similarity	NPD9268	Approved
0.7179	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2354	Approved
0.7159	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7133	Intermediate Similarity	NPD17	Approved
0.7119	Intermediate Similarity	NPD7286	Phase 2
0.7114	Intermediate Similarity	NPD9545	Approved
0.7095	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7390	Discontinued
0.7088	Intermediate Similarity	NPD8434	Phase 2
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD2313	Discontinued
0.707	Intermediate Similarity	NPD1296	Phase 2
0.7062	Intermediate Similarity	NPD2163	Approved
0.7056	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1201	Approved
0.7037	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5711	Approved
0.7029	Intermediate Similarity	NPD5710	Approved
0.7019	Intermediate Similarity	NPD4308	Phase 3
0.7017	Intermediate Similarity	NPD8312	Approved
0.7017	Intermediate Similarity	NPD8313	Approved
0.7013	Intermediate Similarity	NPD1283	Approved
0.7013	Intermediate Similarity	NPD1876	Approved
0.7011	Intermediate Similarity	NPD4287	Approved
0.7007	Intermediate Similarity	NPD1241	Discontinued
0.7	Intermediate Similarity	NPD5090	Approved
0.7	Intermediate Similarity	NPD7685	Pre-registration
0.7	Intermediate Similarity	NPD6651	Approved
0.7	Intermediate Similarity	NPD5089	Approved
0.6993	Remote Similarity	NPD3972	Approved
0.6993	Remote Similarity	NPD9717	Approved
0.6975	Remote Similarity	NPD4476	Approved
0.6975	Remote Similarity	NPD4477	Approved
0.697	Remote Similarity	NPD3887	Approved
0.6968	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2797	Approved
0.6966	Remote Similarity	NPD7177	Discontinued
0.6954	Remote Similarity	NPD1651	Approved
0.6949	Remote Similarity	NPD2403	Approved
0.6949	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6776	Approved
0.6947	Remote Similarity	NPD6782	Approved
0.6947	Remote Similarity	NPD6778	Approved
0.6947	Remote Similarity	NPD6780	Approved
0.6947	Remote Similarity	NPD6777	Approved
0.6947	Remote Similarity	NPD6779	Approved
0.6947	Remote Similarity	NPD6781	Approved
0.6943	Remote Similarity	NPD6832	Phase 2
0.6937	Remote Similarity	NPD1933	Approved
0.6937	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2353	Approved
0.6933	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7435	Discontinued
0.6918	Remote Similarity	NPD6233	Phase 2
0.6911	Remote Similarity	NPD2493	Approved
0.6911	Remote Similarity	NPD3452	Approved
0.6911	Remote Similarity	NPD3450	Approved
0.6911	Remote Similarity	NPD2494	Approved
0.6909	Remote Similarity	NPD7003	Approved
0.6909	Remote Similarity	NPD8166	Discontinued
0.6905	Remote Similarity	NPD6273	Approved
0.6905	Remote Similarity	NPD5049	Phase 3
0.6903	Remote Similarity	NPD3225	Approved
0.6902	Remote Similarity	NPD8150	Discontinued
0.6901	Remote Similarity	NPD6385	Approved
0.6901	Remote Similarity	NPD6386	Approved
0.6899	Remote Similarity	NPD7095	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