NPASS Compound

Structure

NPC55738 OpenBabel07101719512D 23 25 0 0 1 0 0 0 0 0999 V2000 -4.5708 -0.3282 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 -1.2247 -1.2247 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 0.0000 -1.0000 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 -0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 -0.7765 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 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6390 0.1895 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 2 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 -1.4142 1.4142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 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 -3.8637 -1.0353 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 3 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 16 1 0 0 0 0 7 23 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.07
Volume:	302.699
LogP:	1.274
LogD:	1.204
LogS:	-2.979
# Rotatable Bonds:	2
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	3.213
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.325
MDCK Permeability:	8.485483704134822e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.627
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	97.2009048461914%
Volume Distribution (VD):	0.716
Pgp-substrate:	5.874619960784912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.608
CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.166
CYP2C19-substrate:	0.078
CYP2C9-inhibitor:	0.562
CYP2C9-substrate:	0.763
CYP2D6-inhibitor:	0.19
CYP2D6-substrate:	0.407
CYP3A4-inhibitor:	0.379
CYP3A4-substrate:	0.458

ADMET: Excretion

Clearance (CL):	5.119
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.461
AMES Toxicity:	0.73
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.921
Carcinogencity:	0.207
Eye Corrosion:	0.003
Eye Irritation:	0.249
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC55738

Natural Product ID:	NPC55738
*Common Name:**	Isodarparvinol B
IUPAC Name:	(3R)-3-(2,3-dihydroxy-4-methoxyphenyl)-3,7-dihydroxy-2H-chromen-4-one
Synonyms:
Standard InCHIKey:	JSCRWCUDZWUUSS-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C16H14O7/c1-22-11-5-4-10(13(18)14(11)19)16(21)7-23-12-6-8(17)2-3-9(12)15(16)20/h2-6,17-19,21H,7H2,1H3/t16-/m0/s1
SMILES:	COc1ccc(c(c1O)O)[C@]1(COc2cc(ccc2C1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1075687
PubChem CID:	46878685
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO14114	Dalbergia parviflora	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[514235]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	3.4	uM	PMID[514235]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	1.2	uM	PMID[514235]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[514235]

☑ 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 NPC55738 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	413
0.1-0.2	1725
0.2-0.3	4323
0.3-0.4	10172
0.4-0.5	7586
0.5-0.6	3443
0.6-0.7	4764
0.7-0.8	5334
0.8-0.85	2664
0.85-0.9	1476
0.9-0.95	751
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC474638
0.9801	High Similarity	NPC67876
0.9739	High Similarity	NPC173137
0.9733	High Similarity	NPC141212
0.9671	High Similarity	NPC129684
0.9671	High Similarity	NPC52530
0.9671	High Similarity	NPC299520
0.961	High Similarity	NPC308992
0.9608	High Similarity	NPC152904
0.9605	High Similarity	NPC13858
0.9605	High Similarity	NPC320825
0.9605	High Similarity	NPC326037
0.9603	High Similarity	NPC469550
0.96	High Similarity	NPC31363
0.9551	High Similarity	NPC224280
0.9551	High Similarity	NPC62261
0.9551	High Similarity	NPC234052
0.9545	High Similarity	NPC263449
0.9545	High Similarity	NPC470183
0.9542	High Similarity	NPC471479
0.9542	High Similarity	NPC210084
0.9542	High Similarity	NPC471515
0.9542	High Similarity	NPC99597
0.9539	High Similarity	NPC2928
0.9539	High Similarity	NPC255807
0.9539	High Similarity	NPC31018
0.9536	High Similarity	NPC260979
0.9536	High Similarity	NPC477231
0.9536	High Similarity	NPC55205
0.9536	High Similarity	NPC302950
0.9536	High Similarity	NPC219582
0.9536	High Similarity	NPC257648
0.9536	High Similarity	NPC236637
0.9533	High Similarity	NPC29231
0.9533	High Similarity	NPC267117
0.949	High Similarity	NPC477517
0.9487	High Similarity	NPC41301
0.9477	High Similarity	NPC471500
0.9477	High Similarity	NPC472916
0.9477	High Similarity	NPC265511
0.9477	High Similarity	NPC303255
0.9477	High Similarity	NPC255106
0.9477	High Similarity	NPC235165
0.9477	High Similarity	NPC250922
0.9474	High Similarity	NPC27532
0.9474	High Similarity	NPC325028
0.9474	High Similarity	NPC167091
0.9474	High Similarity	NPC206238
0.9474	High Similarity	NPC18727
0.9474	High Similarity	NPC88645
0.9474	High Similarity	NPC246328
0.9474	High Similarity	NPC256346
0.9474	High Similarity	NPC271779
0.9474	High Similarity	NPC292214
0.947	High Similarity	NPC471229
0.947	High Similarity	NPC200740
0.947	High Similarity	NPC54394
0.947	High Similarity	NPC252933
0.947	High Similarity	NPC125062
0.9467	High Similarity	NPC277032
0.9423	High Similarity	NPC474162
0.9423	High Similarity	NPC472964
0.9423	High Similarity	NPC474150
0.9419	High Similarity	NPC474960
0.9419	High Similarity	NPC282009
0.9419	High Similarity	NPC287328
0.9419	High Similarity	NPC472902
0.9416	High Similarity	NPC181960
0.9416	High Similarity	NPC474836
0.9416	High Similarity	NPC472910
0.9416	High Similarity	NPC48208
0.9416	High Similarity	NPC469584
0.9416	High Similarity	NPC222814
0.9416	High Similarity	NPC472963
0.9416	High Similarity	NPC291508
0.9416	High Similarity	NPC472913
0.9416	High Similarity	NPC472914
0.9416	High Similarity	NPC156057
0.9416	High Similarity	NPC27337
0.9416	High Similarity	NPC96167
0.9416	High Similarity	NPC162869
0.9416	High Similarity	NPC472911
0.9416	High Similarity	NPC245758
0.9416	High Similarity	NPC474208
0.9416	High Similarity	NPC475267
0.9412	High Similarity	NPC117992
0.9412	High Similarity	NPC26227
0.9412	High Similarity	NPC230149
0.9412	High Similarity	NPC168247
0.9412	High Similarity	NPC201451
0.9412	High Similarity	NPC256925
0.9412	High Similarity	NPC57674
0.9412	High Similarity	NPC152951
0.9412	High Similarity	NPC44079
0.9408	High Similarity	NPC246162
0.9408	High Similarity	NPC260491
0.9408	High Similarity	NPC60972
0.9408	High Similarity	NPC199100
0.9408	High Similarity	NPC472912
0.9408	High Similarity	NPC36835
0.9408	High Similarity	NPC180234
0.9408	High Similarity	NPC39732
0.9408	High Similarity	NPC101996
0.9408	High Similarity	NPC61506
0.9408	High Similarity	NPC39007
0.9408	High Similarity	NPC120537
0.9408	High Similarity	NPC279989
0.9408	High Similarity	NPC240476
0.9408	High Similarity	NPC9743
0.9408	High Similarity	NPC82325
0.9408	High Similarity	NPC161277
0.94	High Similarity	NPC196277
0.94	High Similarity	NPC272721
0.94	High Similarity	NPC43669
0.9367	High Similarity	NPC235610
0.9363	High Similarity	NPC124038
0.9363	High Similarity	NPC472625
0.9359	High Similarity	NPC471499
0.9359	High Similarity	NPC134783
0.9355	High Similarity	NPC204879
0.9355	High Similarity	NPC476242
0.9355	High Similarity	NPC22192
0.9351	High Similarity	NPC472907
0.9351	High Similarity	NPC133970
0.9351	High Similarity	NPC245546
0.9351	High Similarity	NPC278778
0.9351	High Similarity	NPC6633
0.9351	High Similarity	NPC247017
0.9351	High Similarity	NPC5322
0.9351	High Similarity	NPC291878
0.9351	High Similarity	NPC98661
0.9351	High Similarity	NPC49824
0.9351	High Similarity	NPC43243
0.9351	High Similarity	NPC24640
0.9351	High Similarity	NPC201837
0.9351	High Similarity	NPC195796
0.9351	High Similarity	NPC35038
0.9351	High Similarity	NPC266960
0.9351	High Similarity	NPC472455
0.9346	High Similarity	NPC472905
0.9346	High Similarity	NPC273462
0.9346	High Similarity	NPC472915
0.9346	High Similarity	NPC78326
0.9346	High Similarity	NPC270620
0.9346	High Similarity	NPC236223
0.9346	High Similarity	NPC33051
0.9346	High Similarity	NPC227337
0.9346	High Similarity	NPC203080
0.9346	High Similarity	NPC70433
0.9346	High Similarity	NPC49402
0.9346	High Similarity	NPC179126
0.9342	High Similarity	NPC117579
0.9342	High Similarity	NPC50403
0.9342	High Similarity	NPC28274
0.9342	High Similarity	NPC260895
0.9342	High Similarity	NPC149614
0.9342	High Similarity	NPC171010
0.9342	High Similarity	NPC251110
0.9342	High Similarity	NPC133953
0.9338	High Similarity	NPC137062
0.9338	High Similarity	NPC270465
0.9338	High Similarity	NPC139293
0.9338	High Similarity	NPC183950
0.9338	High Similarity	NPC52005
0.9338	High Similarity	NPC69430
0.9338	High Similarity	NPC264550
0.9338	High Similarity	NPC87125
0.9338	High Similarity	NPC264289
0.9338	High Similarity	NPC183959
0.9338	High Similarity	NPC1612
0.9338	High Similarity	NPC333691
0.9338	High Similarity	NPC287101
0.9338	High Similarity	NPC142876
0.9338	High Similarity	NPC105512
0.9338	High Similarity	NPC200060
0.9338	High Similarity	NPC223579
0.9338	High Similarity	NPC40290
0.9338	High Similarity	NPC159103
0.9338	High Similarity	NPC195763
0.9333	High Similarity	NPC95864
0.9333	High Similarity	NPC77378
0.9304	High Similarity	NPC300053
0.9304	High Similarity	NPC472277
0.9304	High Similarity	NPC108433
0.9299	High Similarity	NPC472448
0.9299	High Similarity	NPC474034
0.9299	High Similarity	NPC83922
0.9299	High Similarity	NPC474033
0.9295	High Similarity	NPC476980
0.9295	High Similarity	NPC472624
0.9295	High Similarity	NPC119209
0.9295	High Similarity	NPC139036
0.9295	High Similarity	NPC192686
0.9295	High Similarity	NPC118256
0.9295	High Similarity	NPC471744
0.9295	High Similarity	NPC36217
0.9295	High Similarity	NPC470326
0.929	High Similarity	NPC219867
0.929	High Similarity	NPC136674
0.929	High Similarity	NPC75215

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 NPC55738 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	975
0.2-0.3	1762
0.3-0.4	2602
0.4-0.5	1761
0.5-0.6	1003
0.6-0.7	462
0.7-0.8	150
0.8-0.85	35
0.85-0.9	11
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9536	High Similarity	NPD1934	Approved
0.9351	High Similarity	NPD3882	Suspended
0.9221	High Similarity	NPD2393	Clinical (unspecified phase)
0.9221	High Similarity	NPD2801	Approved
0.9182	High Similarity	NPD6168	Clinical (unspecified phase)
0.9182	High Similarity	NPD6167	Clinical (unspecified phase)
0.9182	High Similarity	NPD6166	Phase 2
0.9139	High Similarity	NPD1512	Approved
0.9007	High Similarity	NPD1511	Approved
0.8917	High Similarity	NPD3817	Phase 2
0.8834	High Similarity	NPD3818	Discontinued
0.8742	High Similarity	NPD4868	Clinical (unspecified phase)
0.8727	High Similarity	NPD7074	Phase 3
0.8701	High Similarity	NPD4378	Clinical (unspecified phase)
0.8696	High Similarity	NPD5494	Approved
0.8688	High Similarity	NPD7075	Discontinued
0.8683	High Similarity	NPD4338	Clinical (unspecified phase)
0.8675	High Similarity	NPD6797	Phase 2
0.8675	High Similarity	NPD1549	Phase 2
0.8667	High Similarity	NPD7054	Approved
0.8623	High Similarity	NPD7251	Discontinued
0.8616	High Similarity	NPD7096	Clinical (unspecified phase)
0.8614	High Similarity	NPD7472	Approved
0.8609	High Similarity	NPD1550	Clinical (unspecified phase)
0.8609	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD7808	Phase 3
0.8544	High Similarity	NPD4380	Phase 2
0.8516	High Similarity	NPD6799	Approved
0.85	High Similarity	NPD1465	Phase 2
0.8477	Intermediate Similarity	NPD1510	Phase 2
0.8457	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD6599	Discontinued
0.8385	Intermediate Similarity	NPD7819	Suspended
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD943	Approved
0.8333	Intermediate Similarity	NPD1240	Approved
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD3926	Phase 2
0.8303	Intermediate Similarity	NPD1247	Approved
0.8301	Intermediate Similarity	NPD2796	Approved
0.8228	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD5844	Phase 1
0.8224	Intermediate Similarity	NPD1607	Approved
0.8221	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD5402	Approved
0.8182	Intermediate Similarity	NPD919	Approved
0.8148	Intermediate Similarity	NPD7411	Suspended
0.8121	Intermediate Similarity	NPD3749	Approved
0.8117	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1613	Approved
0.8084	Intermediate Similarity	NPD6959	Discontinued
0.8067	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD3751	Discontinued
0.8039	Intermediate Similarity	NPD230	Phase 1
0.8012	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD3750	Approved
0.7962	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD447	Suspended
0.7911	Intermediate Similarity	NPD2800	Approved
0.7898	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7768	Phase 2
0.7834	Intermediate Similarity	NPD1551	Phase 2
0.7824	Intermediate Similarity	NPD3787	Discontinued
0.7812	Intermediate Similarity	NPD6190	Approved
0.7791	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2344	Approved
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD3027	Phase 3
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7772	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD9494	Approved
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7722	Intermediate Similarity	NPD6099	Approved
0.7722	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD2935	Discontinued
0.7697	Intermediate Similarity	NPD3226	Approved
0.7692	Intermediate Similarity	NPD1933	Approved
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD920	Approved
0.7673	Intermediate Similarity	NPD2346	Discontinued
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7199	Phase 2
0.7658	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD3748	Approved
0.7647	Intermediate Similarity	NPD6234	Discontinued
0.764	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2309	Approved
0.7571	Intermediate Similarity	NPD7685	Pre-registration
0.7561	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8434	Phase 2
0.7547	Intermediate Similarity	NPD2799	Discontinued
0.7531	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1653	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5242	Approved
0.7469	Intermediate Similarity	NPD1243	Approved
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7456	Intermediate Similarity	NPD37	Approved
0.7443	Intermediate Similarity	NPD7228	Approved
0.7439	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2403	Approved
0.7427	Intermediate Similarity	NPD4966	Approved
0.7427	Intermediate Similarity	NPD4965	Approved
0.7427	Intermediate Similarity	NPD4967	Phase 2
0.7403	Intermediate Similarity	NPD1203	Approved
0.7389	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD7435	Discontinued
0.7358	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD9269	Phase 2
0.7314	Intermediate Similarity	NPD5710	Approved
0.7314	Intermediate Similarity	NPD5711	Approved
0.7312	Intermediate Similarity	NPD6651	Approved
0.7289	Intermediate Similarity	NPD7390	Discontinued
0.7278	Intermediate Similarity	NPD6798	Discontinued
0.7277	Intermediate Similarity	NPD7697	Approved
0.7277	Intermediate Similarity	NPD7698	Approved
0.7277	Intermediate Similarity	NPD7696	Phase 3
0.7273	Intermediate Similarity	NPD2354	Approved
0.7267	Intermediate Similarity	NPD5353	Approved
0.7261	Intermediate Similarity	NPD6832	Phase 2
0.725	Intermediate Similarity	NPD6355	Discontinued
0.7246	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2798	Approved
0.724	Intermediate Similarity	NPD7870	Phase 2
0.724	Intermediate Similarity	NPD7871	Phase 2
0.7239	Intermediate Similarity	NPD1471	Phase 3
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7219	Intermediate Similarity	NPD1548	Phase 1
0.7219	Intermediate Similarity	NPD6535	Approved
0.7219	Intermediate Similarity	NPD6534	Approved
0.7219	Intermediate Similarity	NPD4363	Phase 3
0.7219	Intermediate Similarity	NPD4360	Phase 2
0.7216	Intermediate Similarity	NPD7701	Phase 2
0.7215	Intermediate Similarity	NPD4625	Phase 3
0.7208	Intermediate Similarity	NPD9717	Approved
0.7208	Intermediate Similarity	NPD1608	Approved
0.7193	Intermediate Similarity	NPD6386	Approved
0.7193	Intermediate Similarity	NPD6385	Approved
0.7189	Intermediate Similarity	NPD4287	Approved
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.7179	Intermediate Similarity	NPD1470	Approved
0.7179	Intermediate Similarity	NPD8151	Discontinued
0.7173	Intermediate Similarity	NPD2494	Approved
0.7173	Intermediate Similarity	NPD2493	Approved
0.717	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD3268	Approved
0.7165	Intermediate Similarity	NPD7584	Approved
0.7161	Intermediate Similarity	NPD4749	Approved
0.7151	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7549	Discontinued
0.7143	Intermediate Similarity	NPD7874	Approved
0.7129	Intermediate Similarity	NPD7907	Approved
0.7125	Intermediate Similarity	NPD6233	Phase 2
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.7114	Intermediate Similarity	NPD4111	Phase 1
0.7114	Intermediate Similarity	NPD4665	Approved
0.7107	Intermediate Similarity	NPD7801	Approved
0.7107	Intermediate Similarity	NPD7095	Approved
0.7105	Intermediate Similarity	NPD7700	Phase 2
0.7105	Intermediate Similarity	NPD7699	Phase 2
0.7093	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2424	Discontinued
0.7089	Intermediate Similarity	NPD2861	Phase 2
0.7083	Intermediate Similarity	NPD3452	Approved
0.7083	Intermediate Similarity	NPD4357	Discontinued
0.7083	Intermediate Similarity	NPD3450	Approved
0.7076	Intermediate Similarity	NPD7458	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