NPASS Compound

Structure

NPC67876 OpenBabel07101718192D 23 25 0 0 1 0 0 0 0 0999 V2000 4.1225 2.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5176 1.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7765 2.8978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1907 1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2247 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7424 3.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4495 2.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0012 4.1225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4154 2.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 5 2 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 17 1 0 0 0 0 9 23 1 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	311.205
LogP:	2.034
LogD:	2.483
LogS:	-3.183
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	3.119
Fsp3:	0.235
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:	-4.801
MDCK Permeability:	1.1981816896877717e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.214
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.791
30% Bioavailability (F30%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	95.94721221923828%
Volume Distribution (VD):	0.586
Pgp-substrate:	2.981557607650757%

ADMET: Metabolism

CYP1A2-inhibitor:	0.916
CYP1A2-substrate:	0.702
CYP2C19-inhibitor:	0.771
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.754
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.676
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.59

ADMET: Excretion

Clearance (CL):	12.757
Half-life (T1/2):	0.866

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.338
AMES Toxicity:	0.695
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.218
Skin Sensitization:	0.56
Carcinogencity:	0.412
Eye Corrosion:	0.003
Eye Irritation:	0.318
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC67876

Natural Product ID:	NPC67876
*Common Name:**	Caesalpiniaphenol A
IUPAC Name:	(3R)-3,7-dihydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2H-chromen-4-one
Synonyms:	Caesalpiniaphenol A
Standard InCHIKey:	IZXFOZCITJGROS-QGZVFWFLSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-22-15-6-10(2-5-13(15)19)8-17(21)9-23-14-7-11(18)3-4-12(14)16(17)20/h2-7,18-19,21H,8-9H2,1H3/t17-/m1/s1
SMILES:	COc1cc(ccc1O)C[C@@]1(O)COc2c(C1=O)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208389
PubChem CID:	71454364
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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[575719]
NPT35	Others	n.a.		IC50	=	102560.0	nM	PMID[575719]

☑ 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 NPC67876 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	408
0.1-0.2	1713
0.2-0.3	4514
0.3-0.4	10491
0.4-0.5	7161
0.5-0.6	3480
0.6-0.7	4759
0.7-0.8	5356
0.8-0.85	2609
0.85-0.9	1457
0.9-0.95	689
0.95-1	60

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC55738
0.98	High Similarity	NPC474638
0.9799	High Similarity	NPC141212
0.9735	High Similarity	NPC471515
0.9735	High Similarity	NPC52530
0.9735	High Similarity	NPC471479
0.9671	High Similarity	NPC152904
0.9669	High Similarity	NPC471500
0.9669	High Similarity	NPC320825
0.9669	High Similarity	NPC13858
0.9669	High Similarity	NPC326037
0.9667	High Similarity	NPC18727
0.9608	High Similarity	NPC287328
0.9608	High Similarity	NPC282009
0.9608	High Similarity	NPC470183
0.9605	High Similarity	NPC291508
0.9605	High Similarity	NPC27337
0.9605	High Similarity	NPC299520
0.9605	High Similarity	NPC129684
0.96	High Similarity	NPC219582
0.96	High Similarity	NPC55205
0.96	High Similarity	NPC302950
0.96	High Similarity	NPC477231
0.96	High Similarity	NPC472912
0.96	High Similarity	NPC236637
0.96	High Similarity	NPC257648
0.9548	High Similarity	NPC472625
0.9545	High Similarity	NPC471499
0.9545	High Similarity	NPC173137
0.9545	High Similarity	NPC308992
0.9542	High Similarity	NPC22192
0.9539	High Similarity	NPC250922
0.9539	High Similarity	NPC472916
0.9539	High Similarity	NPC278778
0.9539	High Similarity	NPC291878
0.9539	High Similarity	NPC303255
0.9539	High Similarity	NPC265511
0.9539	High Similarity	NPC35038
0.9539	High Similarity	NPC195796
0.9536	High Similarity	NPC236223
0.9536	High Similarity	NPC325028
0.9536	High Similarity	NPC246328
0.9536	High Similarity	NPC270620
0.9536	High Similarity	NPC78326
0.9536	High Similarity	NPC256346
0.9536	High Similarity	NPC469550
0.9536	High Similarity	NPC179126
0.9536	High Similarity	NPC27532
0.9533	High Similarity	NPC200740
0.9533	High Similarity	NPC125062
0.9533	High Similarity	NPC31363
0.9533	High Similarity	NPC54394
0.9533	High Similarity	NPC252933
0.9487	High Similarity	NPC224280
0.9487	High Similarity	NPC234052
0.9487	High Similarity	NPC62261
0.9484	High Similarity	NPC474034
0.9484	High Similarity	NPC472964
0.9484	High Similarity	NPC474033
0.9481	High Similarity	NPC470326
0.9481	High Similarity	NPC118256
0.9481	High Similarity	NPC474960
0.9481	High Similarity	NPC192686
0.9481	High Similarity	NPC119209
0.9481	High Similarity	NPC472624
0.9481	High Similarity	NPC472902
0.9481	High Similarity	NPC263449
0.9477	High Similarity	NPC472910
0.9477	High Similarity	NPC52889
0.9477	High Similarity	NPC474836
0.9477	High Similarity	NPC48208
0.9477	High Similarity	NPC472913
0.9477	High Similarity	NPC472963
0.9477	High Similarity	NPC96167
0.9477	High Similarity	NPC472914
0.9477	High Similarity	NPC99597
0.9477	High Similarity	NPC162869
0.9477	High Similarity	NPC156057
0.9477	High Similarity	NPC245758
0.9477	High Similarity	NPC472598
0.9477	High Similarity	NPC222814
0.9477	High Similarity	NPC474208
0.9477	High Similarity	NPC472911
0.9477	High Similarity	NPC210084
0.9477	High Similarity	NPC475267
0.9477	High Similarity	NPC474055
0.9474	High Similarity	NPC31018
0.9474	High Similarity	NPC117992
0.9474	High Similarity	NPC230149
0.9474	High Similarity	NPC2928
0.9474	High Similarity	NPC234255
0.9474	High Similarity	NPC255807
0.9474	High Similarity	NPC45849
0.9474	High Similarity	NPC200761
0.9474	High Similarity	NPC57674
0.9474	High Similarity	NPC470327
0.9474	High Similarity	NPC256925
0.9474	High Similarity	NPC168247
0.9474	High Similarity	NPC152951
0.9474	High Similarity	NPC477503
0.947	High Similarity	NPC260491
0.947	High Similarity	NPC240476
0.947	High Similarity	NPC260979
0.947	High Similarity	NPC9743
0.947	High Similarity	NPC279989
0.947	High Similarity	NPC36835
0.947	High Similarity	NPC60972
0.947	High Similarity	NPC39732
0.947	High Similarity	NPC82325
0.947	High Similarity	NPC246162
0.947	High Similarity	NPC61506
0.9467	High Similarity	NPC338131
0.9467	High Similarity	NPC50728
0.9467	High Similarity	NPC166753
0.9467	High Similarity	NPC29231
0.9427	High Similarity	NPC477517
0.9427	High Similarity	NPC471213
0.9423	High Similarity	NPC41301
0.9423	High Similarity	NPC124038
0.9419	High Similarity	NPC474038
0.9419	High Similarity	NPC472632
0.9419	High Similarity	NPC112418
0.9419	High Similarity	NPC472634
0.9419	High Similarity	NPC471210
0.9419	High Similarity	NPC134783
0.9416	High Similarity	NPC204879
0.9416	High Similarity	NPC184755
0.9416	High Similarity	NPC74178
0.9412	High Similarity	NPC209614
0.9412	High Similarity	NPC235165
0.9412	High Similarity	NPC472626
0.9412	High Similarity	NPC470328
0.9412	High Similarity	NPC255106
0.9412	High Similarity	NPC24640
0.9412	High Similarity	NPC49824
0.9412	High Similarity	NPC472455
0.9412	High Similarity	NPC472907
0.9408	High Similarity	NPC206238
0.9408	High Similarity	NPC49402
0.9408	High Similarity	NPC70433
0.9408	High Similarity	NPC33051
0.9408	High Similarity	NPC213896
0.9408	High Similarity	NPC162351
0.9408	High Similarity	NPC472905
0.9408	High Similarity	NPC88645
0.9408	High Similarity	NPC192083
0.9408	High Similarity	NPC292214
0.9408	High Similarity	NPC227337
0.9408	High Similarity	NPC74924
0.9408	High Similarity	NPC271779
0.9408	High Similarity	NPC472915
0.9408	High Similarity	NPC167091
0.9408	High Similarity	NPC58382
0.9408	High Similarity	NPC273462
0.9404	High Similarity	NPC236769
0.9404	High Similarity	NPC471229
0.9404	High Similarity	NPC260895
0.9404	High Similarity	NPC50403
0.9404	High Similarity	NPC28274
0.9404	High Similarity	NPC133953
0.94	High Similarity	NPC137062
0.94	High Similarity	NPC183950
0.94	High Similarity	NPC183959
0.94	High Similarity	NPC270465
0.94	High Similarity	NPC159103
0.94	High Similarity	NPC52005
0.94	High Similarity	NPC87125
0.94	High Similarity	NPC287101
0.94	High Similarity	NPC177298
0.94	High Similarity	NPC223579
0.94	High Similarity	NPC1612
0.94	High Similarity	NPC105512
0.94	High Similarity	NPC48479
0.9396	High Similarity	NPC472918
0.9396	High Similarity	NPC95864
0.9363	High Similarity	NPC36
0.9363	High Similarity	NPC108433
0.9363	High Similarity	NPC72787
0.9363	High Similarity	NPC7688
0.9363	High Similarity	NPC58223
0.9363	High Similarity	NPC300053
0.9363	High Similarity	NPC7154
0.9363	High Similarity	NPC125039
0.9363	High Similarity	NPC36916
0.9359	High Similarity	NPC474162
0.9359	High Similarity	NPC472635
0.9359	High Similarity	NPC472448
0.9359	High Similarity	NPC476247
0.9359	High Similarity	NPC83922
0.9359	High Similarity	NPC471745
0.9359	High Similarity	NPC474150
0.9355	High Similarity	NPC472631
0.9355	High Similarity	NPC476980
0.9355	High Similarity	NPC328102
0.9355	High Similarity	NPC471744
0.9355	High Similarity	NPC475784
0.9355	High Similarity	NPC36217
0.9355	High Similarity	NPC472630
0.9355	High Similarity	NPC174953
0.9351	High Similarity	NPC93376

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 NPC67876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	977
0.2-0.3	1788
0.3-0.4	2586
0.4-0.5	1766
0.5-0.6	991
0.6-0.7	473
0.7-0.8	139
0.8-0.85	36
0.85-0.9	11
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.96	High Similarity	NPD1934	Approved
0.9412	High Similarity	NPD3882	Suspended
0.9408	High Similarity	NPD2393	Clinical (unspecified phase)
0.9363	High Similarity	NPD6166	Phase 2
0.9363	High Similarity	NPD6168	Clinical (unspecified phase)
0.9363	High Similarity	NPD6167	Clinical (unspecified phase)
0.9281	High Similarity	NPD2801	Approved
0.92	High Similarity	NPD1512	Approved
0.9097	High Similarity	NPD3817	Phase 2
0.9067	High Similarity	NPD1511	Approved
0.8896	High Similarity	NPD7074	Phase 3
0.8889	High Similarity	NPD3818	Discontinued
0.8882	High Similarity	NPD4378	Clinical (unspecified phase)
0.8861	High Similarity	NPD7075	Discontinued
0.8841	High Similarity	NPD6797	Phase 2
0.8834	High Similarity	NPD7054	Approved
0.8797	High Similarity	NPD4868	Clinical (unspecified phase)
0.879	High Similarity	NPD7096	Clinical (unspecified phase)
0.8788	High Similarity	NPD7251	Discontinued
0.878	High Similarity	NPD7472	Approved
0.8735	High Similarity	NPD7808	Phase 3
0.8735	High Similarity	NPD4338	Clinical (unspecified phase)
0.8733	High Similarity	NPD1549	Phase 2
0.8718	High Similarity	NPD4380	Phase 2
0.8693	High Similarity	NPD6799	Approved
0.8667	High Similarity	NPD1550	Clinical (unspecified phase)
0.8667	High Similarity	NPD1552	Clinical (unspecified phase)
0.8634	High Similarity	NPD5494	Approved
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8533	High Similarity	NPD1510	Phase 2
0.8503	High Similarity	NPD7993	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6801	Discontinued
0.8481	Intermediate Similarity	NPD6599	Discontinued
0.8477	Intermediate Similarity	NPD2796	Approved
0.8438	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1240	Approved
0.8383	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1465	Phase 2
0.8313	Intermediate Similarity	NPD7411	Suspended
0.8303	Intermediate Similarity	NPD6232	Discontinued
0.8278	Intermediate Similarity	NPD1607	Approved
0.8274	Intermediate Similarity	NPD5844	Phase 1
0.8272	Intermediate Similarity	NPD5402	Approved
0.8272	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD943	Approved
0.8263	Intermediate Similarity	NPD7473	Discontinued
0.8253	Intermediate Similarity	NPD3926	Phase 2
0.8242	Intermediate Similarity	NPD1247	Approved
0.8232	Intermediate Similarity	NPD919	Approved
0.8176	Intermediate Similarity	NPD5403	Approved
0.8146	Intermediate Similarity	NPD1613	Approved
0.8146	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD6559	Discontinued
0.8121	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5401	Approved
0.7988	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD230	Phase 1
0.7952	Intermediate Similarity	NPD3749	Approved
0.795	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD3027	Phase 3
0.7935	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3750	Approved
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3751	Discontinued
0.7892	Intermediate Similarity	NPD7768	Phase 2
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7885	Intermediate Similarity	NPD1551	Phase 2
0.7862	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD447	Suspended
0.7848	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6100	Approved
0.7771	Intermediate Similarity	NPD6099	Approved
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD1933	Approved
0.7736	Intermediate Similarity	NPD2800	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2534	Approved
0.7716	Intermediate Similarity	NPD2533	Approved
0.7716	Intermediate Similarity	NPD2532	Approved
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD9494	Approved
0.7683	Intermediate Similarity	NPD1653	Approved
0.7667	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD920	Approved
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2344	Approved
0.7595	Intermediate Similarity	NPD3748	Approved
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7578	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.7543	Intermediate Similarity	NPD7286	Phase 2
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4908	Phase 1
0.753	Intermediate Similarity	NPD3226	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6651	Approved
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1203	Approved
0.7436	Intermediate Similarity	NPD6798	Discontinued
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7423	Intermediate Similarity	NPD2309	Approved
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7414	Intermediate Similarity	NPD5242	Approved
0.7405	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7396	Intermediate Similarity	NPD37	Approved
0.7386	Intermediate Similarity	NPD7228	Approved
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7371	Intermediate Similarity	NPD2403	Approved
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD7390	Discontinued
0.7333	Intermediate Similarity	NPD8312	Approved
0.7317	Intermediate Similarity	NPD2354	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.731	Intermediate Similarity	NPD5353	Approved
0.7296	Intermediate Similarity	NPD6355	Discontinued
0.7292	Intermediate Similarity	NPD7584	Approved
0.729	Intermediate Similarity	NPD2798	Approved
0.7289	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7261	Intermediate Similarity	NPD4625	Phase 3
0.7258	Intermediate Similarity	NPD4360	Phase 2
0.7258	Intermediate Similarity	NPD4363	Phase 3
0.7257	Intermediate Similarity	NPD5711	Approved
0.7257	Intermediate Similarity	NPD5710	Approved
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7255	Intermediate Similarity	NPD9717	Approved
0.7235	Intermediate Similarity	NPD6386	Approved
0.7235	Intermediate Similarity	NPD6385	Approved
0.7233	Intermediate Similarity	NPD4060	Phase 1
0.7225	Intermediate Similarity	NPD7698	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7225	Intermediate Similarity	NPD7697	Approved
0.7215	Intermediate Similarity	NPD3268	Approved
0.7212	Intermediate Similarity	NPD3887	Approved
0.7208	Intermediate Similarity	NPD4749	Approved
0.72	Intermediate Similarity	NPD5536	Phase 2
0.7193	Intermediate Similarity	NPD6844	Discontinued
0.7191	Intermediate Similarity	NPD2163	Approved
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7549	Discontinued
0.7178	Intermediate Similarity	NPD7266	Discontinued
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7134	Intermediate Similarity	NPD2861	Phase 2
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.7126	Intermediate Similarity	NPD4357	Discontinued
0.712	Intermediate Similarity	NPD2494	Approved
0.712	Intermediate Similarity	NPD2493	Approved
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD2797	Approved
0.7107	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD411	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7091	Intermediate Similarity	NPD1652	Phase 2

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