NPASS Compound

Structure

CID130015 OpenBabel06191715492D 22 25 0 0 0 0 0 0 0 0999 V2000 5.1962 -0.0000 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 1.7321 -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 2.0000 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 -1.9400 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 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 0.8660 1.5000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 0.0000 2.0000 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 0.8660 0.5000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.1691 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 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 21 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.07
Volume:	297.091
LogP:	4.428
LogD:	3.081
LogS:	-6.481
# Rotatable Bonds:	2
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	2.283
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.693
MDCK Permeability:	2.8794533136533573e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	92.36952209472656%
Volume Distribution (VD):	0.744
Pgp-substrate:	6.981348037719727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.875
CYP2C19-inhibitor:	0.816
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.624
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.678
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.812
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	5.625
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.289
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.371
Rat Oral Acute Toxicity:	0.662
Maximum Recommended Daily Dose:	0.614
Skin Sensitization:	0.158
Carcinogencity:	0.769
Eye Corrosion:	0.003
Eye Irritation:	0.681
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC130015

Natural Product ID:	NPC130015
*Common Name:**	3'-Methoxy-[2'',3'':7,8]-Furanoflavone
IUPAC Name:	2-(3-methoxyphenyl)furo[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	OHKLPDQPGIVELF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O4/c1-20-12-4-2-3-11(9-12)17-10-15(19)13-5-6-16-14(7-8-21-16)18(13)22-17/h2-10H,1H3
SMILES:	COc1cccc(c1)c1cc(=O)c2c(o1)c1ccoc1cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581062
PubChem CID:	636768
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001759] Furanoflavones

*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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22458	Fordia cauliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22458	Fordia cauliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22458	Fordia cauliflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	100000.0	nM	PMID[449668]

☑ 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 NPC130015 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	603
0.1-0.2	2228
0.2-0.3	5245
0.3-0.4	12254
0.4-0.5	5341
0.5-0.6	4915
0.6-0.7	5678
0.7-0.8	4431
0.8-0.85	1651
0.85-0.9	320
0.9-0.95	23
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC38361
0.9864	High Similarity	NPC233776
0.9862	High Similarity	NPC135303
0.9862	High Similarity	NPC148423
0.9724	High Similarity	NPC306788
0.9662	High Similarity	NPC41719
0.966	High Similarity	NPC472407
0.9655	High Similarity	NPC198427
0.9586	High Similarity	NPC190572
0.9477	High Similarity	NPC193998
0.9463	High Similarity	NPC263676
0.9459	High Similarity	NPC472406
0.9416	High Similarity	NPC65846
0.9333	High Similarity	NPC253872
0.9267	High Similarity	NPC116604
0.9262	High Similarity	NPC88445
0.9231	High Similarity	NPC38914
0.92	High Similarity	NPC191104
0.9184	High Similarity	NPC17262
0.9177	High Similarity	NPC41853
0.9161	High Similarity	NPC304387
0.9145	High Similarity	NPC472462
0.9139	High Similarity	NPC170169
0.9128	High Similarity	NPC74539
0.9128	High Similarity	NPC304443
0.9114	High Similarity	NPC167479
0.9114	High Similarity	NPC241820
0.9085	High Similarity	NPC198490
0.9073	High Similarity	NPC230713
0.9073	High Similarity	NPC78335
0.9038	High Similarity	NPC264293
0.9026	High Similarity	NPC160015
0.9026	High Similarity	NPC247677
0.902	High Similarity	NPC213608
0.902	High Similarity	NPC122365
0.902	High Similarity	NPC183874
0.902	High Similarity	NPC1477
0.9007	High Similarity	NPC226644
0.9007	High Similarity	NPC37226
0.9007	High Similarity	NPC178202
0.9006	High Similarity	NPC62640
0.9	High Similarity	NPC190351
0.9	High Similarity	NPC17816
0.8993	High Similarity	NPC246903
0.8981	High Similarity	NPC219861
0.8968	High Similarity	NPC260902
0.8968	High Similarity	NPC296957
0.8968	High Similarity	NPC65504
0.8968	High Similarity	NPC268360
0.8966	High Similarity	NPC29638
0.8961	High Similarity	NPC148938
0.8954	High Similarity	NPC67654
0.8954	High Similarity	NPC5871
0.894	High Similarity	NPC266743
0.8919	High Similarity	NPC22467
0.891	High Similarity	NPC250076
0.891	High Similarity	NPC476349
0.891	High Similarity	NPC476350
0.891	High Similarity	NPC472877
0.8896	High Similarity	NPC235333
0.8896	High Similarity	NPC72370
0.8889	High Similarity	NPC115324
0.8889	High Similarity	NPC156244
0.8882	High Similarity	NPC37208
0.8882	High Similarity	NPC317492
0.8882	High Similarity	NPC221868
0.8882	High Similarity	NPC39929
0.8882	High Similarity	NPC296030
0.8874	High Similarity	NPC130581
0.8874	High Similarity	NPC12148
0.8867	High Similarity	NPC98926
0.8867	High Similarity	NPC155144
0.8867	High Similarity	NPC208584
0.8859	High Similarity	NPC51146
0.8859	High Similarity	NPC166858
0.8859	High Similarity	NPC313036
0.8846	High Similarity	NPC269495
0.8846	High Similarity	NPC212967
0.8846	High Similarity	NPC246647
0.8846	High Similarity	NPC164110
0.8846	High Similarity	NPC96342
0.8839	High Similarity	NPC295608
0.8839	High Similarity	NPC297531
0.8839	High Similarity	NPC213936
0.8839	High Similarity	NPC278010
0.8839	High Similarity	NPC250769
0.8839	High Similarity	NPC99199
0.8836	High Similarity	NPC254741
0.8834	High Similarity	NPC66804
0.8831	High Similarity	NPC207624
0.8827	High Similarity	NPC157522
0.8824	High Similarity	NPC167576
0.8816	High Similarity	NPC168085
0.8816	High Similarity	NPC135325
0.8816	High Similarity	NPC272194
0.8808	High Similarity	NPC300267
0.8808	High Similarity	NPC210826
0.8808	High Similarity	NPC51641
0.8805	High Similarity	NPC472581
0.8805	High Similarity	NPC109180
0.88	High Similarity	NPC225884
0.88	High Similarity	NPC302181
0.8797	High Similarity	NPC74854
0.8797	High Similarity	NPC30655
0.8797	High Similarity	NPC45124
0.879	High Similarity	NPC40583
0.8782	High Similarity	NPC180924
0.8774	High Similarity	NPC131725
0.8773	High Similarity	NPC72455
0.8766	High Similarity	NPC106372
0.8766	High Similarity	NPC23668
0.8766	High Similarity	NPC58668
0.8766	High Similarity	NPC193976
0.8765	High Similarity	NPC131866
0.8759	High Similarity	NPC292998
0.875	High Similarity	NPC136641
0.8742	High Similarity	NPC179970
0.8742	High Similarity	NPC230943
0.8734	High Similarity	NPC220582
0.8734	High Similarity	NPC49009
0.8734	High Similarity	NPC169
0.8734	High Similarity	NPC243509
0.8734	High Similarity	NPC304839
0.8733	High Similarity	NPC53192
0.8727	High Similarity	NPC472606
0.8726	High Similarity	NPC19097
0.8726	High Similarity	NPC270044
0.871	High Similarity	NPC142308
0.8707	High Similarity	NPC161196
0.8701	High Similarity	NPC155882
0.8696	High Similarity	NPC277480
0.8696	High Similarity	NPC193881
0.8696	High Similarity	NPC67450
0.8696	High Similarity	NPC155264
0.8696	High Similarity	NPC210460
0.869	High Similarity	NPC182428
0.8688	High Similarity	NPC179464
0.8679	High Similarity	NPC14822
0.8679	High Similarity	NPC216092
0.8675	High Similarity	NPC189650
0.8671	High Similarity	NPC33320
0.8667	High Similarity	NPC254010
0.8658	High Similarity	NPC262635
0.8658	High Similarity	NPC136095
0.8658	High Similarity	NPC11566
0.8649	High Similarity	NPC259685
0.8636	High Similarity	NPC266499
0.8634	High Similarity	NPC37183
0.863	High Similarity	NPC223354
0.8627	High Similarity	NPC471285
0.8625	High Similarity	NPC78612
0.8625	High Similarity	NPC234536
0.8621	High Similarity	NPC278556
0.8621	High Similarity	NPC284424
0.8618	High Similarity	NPC234629
0.8618	High Similarity	NPC471590
0.8618	High Similarity	NPC136278
0.8618	High Similarity	NPC110776
0.8618	High Similarity	NPC271590
0.8618	High Similarity	NPC311741
0.8616	High Similarity	NPC239270
0.8616	High Similarity	NPC260296
0.8616	High Similarity	NPC303210
0.8616	High Similarity	NPC115432
0.8616	High Similarity	NPC95472
0.86	High Similarity	NPC171094
0.86	High Similarity	NPC28337
0.86	High Similarity	NPC101366
0.86	High Similarity	NPC472409
0.8598	High Similarity	NPC248593
0.8598	High Similarity	NPC28589
0.8591	High Similarity	NPC17848
0.859	High Similarity	NPC327269
0.859	High Similarity	NPC476238
0.859	High Similarity	NPC40033
0.859	High Similarity	NPC31627
0.8581	High Similarity	NPC321896
0.8581	High Similarity	NPC476185
0.8581	High Similarity	NPC101957
0.8581	High Similarity	NPC37348
0.8581	High Similarity	NPC120105
0.8581	High Similarity	NPC472633
0.8581	High Similarity	NPC5840
0.8581	High Similarity	NPC189270
0.858	High Similarity	NPC53640
0.8571	High Similarity	NPC37135
0.8571	High Similarity	NPC476342
0.8571	High Similarity	NPC39195
0.8571	High Similarity	NPC266572
0.8571	High Similarity	NPC125269
0.8571	High Similarity	NPC186397
0.8563	High Similarity	NPC104682
0.8562	High Similarity	NPC473655
0.8562	High Similarity	NPC2416
0.8562	High Similarity	NPC290133
0.8562	High Similarity	NPC476153
0.8562	High Similarity	NPC101294
0.8562	High Similarity	NPC187282
0.8562	High Similarity	NPC472346
0.8562	High Similarity	NPC215885

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 NPC130015 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	520
0.1-0.2	1019
0.2-0.3	1775
0.3-0.4	2803
0.4-0.5	1772
0.5-0.6	868
0.6-0.7	268
0.7-0.8	96
0.8-0.85	21
0.85-0.9	5
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9128	High Similarity	NPD920	Approved
0.9038	High Similarity	NPD1247	Approved
0.8993	High Similarity	NPD642	Clinical (unspecified phase)
0.8859	High Similarity	NPD643	Clinical (unspecified phase)
0.8707	High Similarity	NPD2796	Approved
0.8671	High Similarity	NPD919	Approved
0.8658	High Similarity	NPD1243	Approved
0.85	High Similarity	NPD5494	Approved
0.8497	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD7411	Suspended
0.8323	Intermediate Similarity	NPD6559	Discontinued
0.8302	Intermediate Similarity	NPD7819	Suspended
0.8302	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1510	Phase 2
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD3926	Phase 2
0.8224	Intermediate Similarity	NPD1549	Phase 2
0.8158	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3749	Approved
0.8125	Intermediate Similarity	NPD1934	Approved
0.8113	Intermediate Similarity	NPD4380	Phase 2
0.8086	Intermediate Similarity	NPD3882	Suspended
0.8077	Intermediate Similarity	NPD1511	Approved
0.8075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD2801	Approved
0.8072	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2344	Approved
0.8025	Intermediate Similarity	NPD3817	Phase 2
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD1240	Approved
0.7976	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD1512	Approved
0.7962	Intermediate Similarity	NPD6799	Approved
0.7935	Intermediate Similarity	NPD2800	Approved
0.7927	Intermediate Similarity	NPD7075	Discontinued
0.7922	Intermediate Similarity	NPD1471	Phase 3
0.7922	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD3748	Approved
0.7895	Intermediate Similarity	NPD1607	Approved
0.787	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7768	Phase 2
0.7834	Intermediate Similarity	NPD2309	Approved
0.7826	Intermediate Similarity	NPD3226	Approved
0.7818	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD2534	Approved
0.7799	Intermediate Similarity	NPD2532	Approved
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7751	Intermediate Similarity	NPD6166	Phase 2
0.7751	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2313	Discontinued
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7738	Intermediate Similarity	NPD6232	Discontinued
0.7706	Intermediate Similarity	NPD7473	Discontinued
0.7702	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5402	Approved
0.7658	Intermediate Similarity	NPD3750	Approved
0.7651	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6808	Phase 2
0.7628	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7597	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7578	Intermediate Similarity	NPD5401	Approved
0.7576	Intermediate Similarity	NPD6280	Approved
0.7576	Intermediate Similarity	NPD6279	Approved
0.7564	Intermediate Similarity	NPD2799	Discontinued
0.7543	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7229	Phase 3
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7485	Intermediate Similarity	NPD5403	Approved
0.7471	Intermediate Similarity	NPD7472	Approved
0.7471	Intermediate Similarity	NPD7074	Phase 3
0.7452	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5953	Discontinued
0.7429	Intermediate Similarity	NPD6797	Phase 2
0.7417	Intermediate Similarity	NPD3266	Approved
0.7417	Intermediate Similarity	NPD3267	Approved
0.7414	Intermediate Similarity	NPD7286	Phase 2
0.7386	Intermediate Similarity	NPD7251	Discontinued
0.7375	Intermediate Similarity	NPD2654	Approved
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7353	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7808	Phase 3
0.7341	Intermediate Similarity	NPD2403	Approved
0.7321	Intermediate Similarity	NPD5761	Phase 2
0.7321	Intermediate Similarity	NPD5760	Phase 2
0.7308	Intermediate Similarity	NPD943	Approved
0.7305	Intermediate Similarity	NPD5889	Approved
0.7305	Intermediate Similarity	NPD5890	Approved
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.7278	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2296	Approved
0.7255	Intermediate Similarity	NPD2798	Approved
0.7232	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5711	Approved
0.7225	Intermediate Similarity	NPD5710	Approved
0.7219	Intermediate Similarity	NPD1465	Phase 2
0.7215	Intermediate Similarity	NPD6651	Approved
0.7198	Intermediate Similarity	NPD4287	Approved
0.7197	Intermediate Similarity	NPD4307	Phase 2
0.7179	Intermediate Similarity	NPD3268	Approved
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD1019	Discontinued
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7133	Intermediate Similarity	NPD17	Approved
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7033	Discontinued
0.7123	Intermediate Similarity	NPD1241	Discontinued
0.7117	Intermediate Similarity	NPD4628	Phase 3
0.7105	Intermediate Similarity	NPD3972	Approved
0.7097	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4361	Phase 2
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6100	Approved
0.7081	Intermediate Similarity	NPD6099	Approved
0.7079	Intermediate Similarity	NPD1729	Discontinued
0.7078	Intermediate Similarity	NPD1203	Approved
0.707	Intermediate Similarity	NPD1296	Phase 2
0.7069	Intermediate Similarity	NPD7199	Phase 2
0.7062	Intermediate Similarity	NPD3751	Discontinued
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7051	Intermediate Similarity	NPD4908	Phase 1
0.7044	Intermediate Similarity	NPD447	Suspended
0.7044	Intermediate Similarity	NPD230	Phase 1
0.7043	Intermediate Similarity	NPD4360	Phase 2
0.7043	Intermediate Similarity	NPD4363	Phase 3
0.7019	Intermediate Similarity	NPD4308	Phase 3
0.7013	Intermediate Similarity	NPD1876	Approved
0.7012	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1548	Phase 1
0.6993	Remote Similarity	NPD1608	Approved
0.6993	Remote Similarity	NPD9717	Approved
0.6989	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5242	Approved
0.6988	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4288	Approved
0.6968	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3764	Approved
0.6954	Remote Similarity	NPD1651	Approved
0.6949	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3787	Discontinued
0.6928	Remote Similarity	NPD1610	Phase 2
0.6923	Remote Similarity	NPD8312	Approved
0.6923	Remote Similarity	NPD8313	Approved
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3225	Approved
0.6899	Remote Similarity	NPD4625	Phase 3
0.6897	Remote Similarity	NPD6971	Discontinued
0.6895	Remote Similarity	NPD8285	Discontinued
0.6875	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD1613	Approved
0.6872	Remote Similarity	NPD2163	Approved
0.6872	Remote Similarity	NPD7177	Discontinued
0.6871	Remote Similarity	NPD5406	Approved
0.6871	Remote Similarity	NPD5404	Approved
0.6871	Remote Similarity	NPD5408	Approved
0.6871	Remote Similarity	NPD5405	Approved
0.6867	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.686	Remote Similarity	NPD37	Approved
0.6859	Remote Similarity	NPD2797	Approved
0.6859	Remote Similarity	NPD1470	Approved
0.6855	Remote Similarity	NPD411	Approved
0.6845	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4965	Approved
0.6839	Remote Similarity	NPD4967	Phase 2
0.6839	Remote Similarity	NPD4966	Approved
0.6835	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5124	Phase 1
0.6832	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD422	Phase 1
0.6818	Remote Similarity	NPD1281	Approved
0.6813	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.681	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7003	Approved
0.6805	Remote Similarity	NPD6273	Approved
0.6802	Remote Similarity	NPD6386	Approved
0.6802	Remote Similarity	NPD6385	Approved
0.6788	Remote Similarity	NPD2424	Discontinued
0.6784	Remote Similarity	NPD7458	Discontinued
0.6782	Remote Similarity	NPD5353	Approved
0.6772	Remote Similarity	NPD9494	Approved
0.6772	Remote Similarity	NPD1530	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data