NPASS Compound

Structure

CID14822 OpenBabel06191715342D 28 30 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 8.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 8.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 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 -0.8660 6.5000 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 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 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 0.0000 5.0000 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 2.5981 1.5000 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 7.5000 0.0000 C 0 0 2 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 8.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 14 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 25 1 0 0 0 0 5 7 1 0 0 0 0 5 14 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 27 1 0 0 0 0 12 26 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 1 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.17
Volume:	397.685
LogP:	3.827
LogD:	3.279
LogS:	-4.31
# Rotatable Bonds:	8
TPSA:	82.04
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	3.576
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.805
MDCK Permeability:	1.7212016246048734e-05
Pgp-inhibitor:	0.438
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.67

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	95.83207702636719%
Volume Distribution (VD):	0.361
Pgp-substrate:	5.393422603607178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.697
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.7
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.648
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.282
CYP3A4-substrate:	0.443

ADMET: Excretion

Clearance (CL):	9.023
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.124
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.245
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.238
Carcinogencity:	0.213
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.62

Download Data

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

Natural Product: NPC14822

Natural Product ID:	NPC14822
*Common Name:**	6'-Hydroxy-7'-Methoxybergamottin
IUPAC Name:	4-[(E,6R)-6-hydroxy-7-methoxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	DXUCGAHPDLXISA-CECLQJIQSA-N
Standard InCHI:	InChI=1S/C22H26O6/c1-14(5-7-19(23)22(2,3)25-4)9-11-27-21-15-6-8-20(24)28-18(15)13-17-16(21)10-12-26-17/h6,8-10,12-13,19,23H,5,7,11H2,1-4H3/b14-9+/t19-/m1/s1
SMILES:	COC([C@@H](CC/C(=C/COc1c2ccoc2cc2c1ccc(=O)o2)/C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651089
PubChem CID:	53316972
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens

*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
NPO30686	Citrus hystrix	Species	Rutaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[20964319]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	3
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2107	Cell Line	PSN1	Homo sapiens	PC50	=	37.8	uM	PMID[549947]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	PC50	=	37.1	uM	PMID[549947]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	37.8	uM	PMID[549947]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	11200.0	nM	PMID[549946]

☑ 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 NPC14822 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	353
0.1-0.2	1509
0.2-0.3	3620
0.3-0.4	8369
0.4-0.5	10453
0.5-0.6	4296
0.6-0.7	5905
0.7-0.8	5214
0.8-0.85	2302
0.85-0.9	513
0.9-0.95	151
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC95472
0.9934	High Similarity	NPC303210
0.9934	High Similarity	NPC49009
0.9934	High Similarity	NPC239270
0.9804	High Similarity	NPC169
0.9673	High Similarity	NPC269495
0.9416	High Similarity	NPC250769
0.9416	High Similarity	NPC278010
0.9416	High Similarity	NPC295608
0.9408	High Similarity	NPC191104
0.9351	High Similarity	NPC131725
0.9342	High Similarity	NPC88445
0.9325	High Similarity	NPC325176
0.9317	High Similarity	NPC51404
0.9264	High Similarity	NPC224165
0.9211	High Similarity	NPC304443
0.9211	High Similarity	NPC74539
0.9207	High Similarity	NPC107244
0.9172	High Similarity	NPC270044
0.9167	High Similarity	NPC108937
0.9167	High Similarity	NPC279218
0.9156	High Similarity	NPC155882
0.9146	High Similarity	NPC53917
0.9141	High Similarity	NPC472584
0.9108	High Similarity	NPC469936
0.9108	High Similarity	NPC321372
0.9108	High Similarity	NPC78554
0.9108	High Similarity	NPC475797
0.9108	High Similarity	NPC474738
0.9108	High Similarity	NPC474609
0.9108	High Similarity	NPC129053
0.9108	High Similarity	NPC109967
0.9097	High Similarity	NPC472423
0.9097	High Similarity	NPC474772
0.9097	High Similarity	NPC474744
0.908	High Similarity	NPC120220
0.9079	High Similarity	NPC246903
0.9068	High Similarity	NPC329215
0.9068	High Similarity	NPC204088
0.9068	High Similarity	NPC259007
0.9038	High Similarity	NPC31627
0.9038	High Similarity	NPC256141
0.9038	High Similarity	NPC476238
0.9038	High Similarity	NPC327269
0.9038	High Similarity	NPC285623
0.9032	High Similarity	NPC470908
0.9032	High Similarity	NPC472421
0.9026	High Similarity	NPC266743
0.9012	High Similarity	NPC323137
0.9	High Similarity	NPC30655
0.9	High Similarity	NPC45124
0.9	High Similarity	NPC74854
0.8994	High Similarity	NPC476349
0.8994	High Similarity	NPC476350
0.8974	High Similarity	NPC471675
0.897	High Similarity	NPC233956
0.8961	High Similarity	NPC202494
0.8954	High Similarity	NPC208584
0.8947	High Similarity	NPC51146
0.8947	High Similarity	NPC166858
0.8947	High Similarity	NPC313036
0.8944	High Similarity	NPC219861
0.8938	High Similarity	NPC220582
0.8938	High Similarity	NPC304839
0.8931	High Similarity	NPC296957
0.8931	High Similarity	NPC260902
0.8924	High Similarity	NPC477530
0.8917	High Similarity	NPC263676
0.8917	High Similarity	NPC473996
0.891	High Similarity	NPC180351
0.891	High Similarity	NPC321387
0.891	High Similarity	NPC327059
0.8896	High Similarity	NPC190572
0.8896	High Similarity	NPC474302
0.8896	High Similarity	NPC155264
0.8896	High Similarity	NPC210460
0.8896	High Similarity	NPC193881
0.8896	High Similarity	NPC67450
0.8889	High Similarity	NPC472581
0.8882	High Similarity	NPC92589
0.8882	High Similarity	NPC216092
0.8868	High Similarity	NPC470625
0.8868	High Similarity	NPC160015
0.8868	High Similarity	NPC19860
0.8868	High Similarity	NPC247677
0.8861	High Similarity	NPC223701
0.8861	High Similarity	NPC472583
0.8861	High Similarity	NPC7989
0.8861	High Similarity	NPC122365
0.8861	High Similarity	NPC469405
0.8854	High Similarity	NPC290671
0.8854	High Similarity	NPC472422
0.8854	High Similarity	NPC244577
0.8854	High Similarity	NPC471676
0.8854	High Similarity	NPC263384
0.8854	High Similarity	NPC472420
0.8854	High Similarity	NPC472580
0.8854	High Similarity	NPC472636
0.8848	High Similarity	NPC281835
0.8848	High Similarity	NPC144288
0.8846	High Similarity	NPC317492
0.8846	High Similarity	NPC37226
0.8846	High Similarity	NPC39929
0.8846	High Similarity	NPC226644
0.8846	High Similarity	NPC296030
0.8841	High Similarity	NPC476459
0.8839	High Similarity	NPC14875
0.8834	High Similarity	NPC136641
0.8834	High Similarity	NPC179015
0.8834	High Similarity	NPC173149
0.8831	High Similarity	NPC171656
0.8831	High Similarity	NPC297788
0.882	High Similarity	NPC260296
0.882	High Similarity	NPC243509
0.882	High Similarity	NPC115432
0.8816	High Similarity	NPC470856
0.8812	High Similarity	NPC65504
0.8805	High Similarity	NPC469934
0.8805	High Similarity	NPC470681
0.8805	High Similarity	NPC474542
0.8797	High Similarity	NPC477957
0.879	High Similarity	NPC474735
0.879	High Similarity	NPC135303
0.879	High Similarity	NPC148423
0.8782	High Similarity	NPC168085
0.878	High Similarity	NPC53640
0.8774	High Similarity	NPC316769
0.8773	High Similarity	NPC155640
0.8773	High Similarity	NPC15819
0.8773	High Similarity	NPC179464
0.8758	High Similarity	NPC244750
0.8758	High Similarity	NPC254010
0.8758	High Similarity	NPC33320
0.875	High Similarity	NPC17521
0.875	High Similarity	NPC262635
0.8742	High Similarity	NPC472462
0.8742	High Similarity	NPC1477
0.8742	High Similarity	NPC213608
0.8734	High Similarity	NPC170169
0.8734	High Similarity	NPC471677
0.8734	High Similarity	NPC116604
0.8734	High Similarity	NPC98028
0.8726	High Similarity	NPC37208
0.8726	High Similarity	NPC164299
0.8726	High Similarity	NPC221868
0.8718	High Similarity	NPC85773
0.8718	High Similarity	NPC91902
0.8718	High Similarity	NPC51070
0.8718	High Similarity	NPC222298
0.8718	High Similarity	NPC285748
0.8718	High Similarity	NPC130581
0.8718	High Similarity	NPC198427
0.8718	High Similarity	NPC473133
0.8718	High Similarity	NPC47388
0.8718	High Similarity	NPC470670
0.8718	High Similarity	NPC12148
0.8712	High Similarity	NPC234536
0.8712	High Similarity	NPC78612
0.871	High Similarity	NPC316535
0.871	High Similarity	NPC294365
0.8704	High Similarity	NPC328102
0.8701	High Similarity	NPC294432
0.8688	High Similarity	NPC198490
0.8688	High Similarity	NPC217706
0.8688	High Similarity	NPC207809
0.8688	High Similarity	NPC259710
0.8688	High Similarity	NPC48579
0.8688	High Similarity	NPC304207
0.8688	High Similarity	NPC473241
0.8688	High Similarity	NPC477958
0.8679	High Similarity	NPC171651
0.8679	High Similarity	NPC67654
0.8679	High Similarity	NPC150123
0.8679	High Similarity	NPC130015
0.8679	High Similarity	NPC161881
0.8679	High Similarity	NPC475790
0.8679	High Similarity	NPC243171
0.8679	High Similarity	NPC10807
0.8679	High Similarity	NPC244583
0.8679	High Similarity	NPC5871
0.8679	High Similarity	NPC56232
0.8679	High Similarity	NPC35567
0.8679	High Similarity	NPC38361
0.8671	High Similarity	NPC472406
0.8671	High Similarity	NPC78335
0.8671	High Similarity	NPC230713
0.8671	High Similarity	NPC61258
0.8662	High Similarity	NPC272194
0.8662	High Similarity	NPC10097
0.8662	High Similarity	NPC135325
0.8662	High Similarity	NPC306788
0.8659	High Similarity	NPC91288
0.8659	High Similarity	NPC124038
0.8659	High Similarity	NPC471286
0.8654	High Similarity	NPC300267
0.8654	High Similarity	NPC51641
0.8654	High Similarity	NPC210826
0.865	High Similarity	NPC97812
0.8645	High Similarity	NPC96216
0.8645	High Similarity	NPC33653

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 NPC14822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	870
0.2-0.3	1817
0.3-0.4	2614
0.4-0.5	1994
0.5-0.6	1022
0.6-0.7	364
0.7-0.8	120
0.8-0.85	26
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD920	Approved
0.9079	High Similarity	NPD642	Clinical (unspecified phase)
0.8947	High Similarity	NPD643	Clinical (unspecified phase)
0.8758	High Similarity	NPD919	Approved
0.875	High Similarity	NPD1243	Approved
0.8742	High Similarity	NPD7096	Clinical (unspecified phase)
0.8679	High Similarity	NPD6801	Discontinued
0.8631	High Similarity	NPD6559	Discontinued
0.858	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD4380	Phase 2
0.8526	High Similarity	NPD6799	Approved
0.8424	Intermediate Similarity	NPD1247	Approved
0.8354	Intermediate Similarity	NPD3749	Approved
0.8354	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8312	Intermediate Similarity	NPD2796	Approved
0.8284	Intermediate Similarity	NPD3818	Discontinued
0.8282	Intermediate Similarity	NPD7819	Suspended
0.8282	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7411	Suspended
0.8232	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD3882	Suspended
0.8144	Intermediate Similarity	NPD5494	Approved
0.8137	Intermediate Similarity	NPD5403	Approved
0.8129	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5401	Approved
0.8121	Intermediate Similarity	NPD5402	Approved
0.811	Intermediate Similarity	NPD1934	Approved
0.8089	Intermediate Similarity	NPD1549	Phase 2
0.8061	Intermediate Similarity	NPD2801	Approved
0.8025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.8013	Intermediate Similarity	NPD1510	Phase 2
0.8012	Intermediate Similarity	NPD2532	Approved
0.8012	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD2534	Approved
0.7987	Intermediate Similarity	NPD4628	Phase 3
0.7966	Intermediate Similarity	NPD8434	Phase 2
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7964	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1551	Phase 2
0.7953	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2800	Approved
0.7904	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2799	Discontinued
0.7875	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1240	Approved
0.7857	Intermediate Similarity	NPD2313	Discontinued
0.7857	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6166	Phase 2
0.7849	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1511	Approved
0.7836	Intermediate Similarity	NPD6232	Discontinued
0.7816	Intermediate Similarity	NPD7054	Approved
0.7803	Intermediate Similarity	NPD7473	Discontinued
0.7799	Intermediate Similarity	NPD2344	Approved
0.7791	Intermediate Similarity	NPD3926	Phase 2
0.7771	Intermediate Similarity	NPD1607	Approved
0.7771	Intermediate Similarity	NPD7472	Approved
0.7771	Intermediate Similarity	NPD7074	Phase 3
0.7764	Intermediate Similarity	NPD3750	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1512	Approved
0.7736	Intermediate Similarity	NPD2935	Discontinued
0.7727	Intermediate Similarity	NPD5953	Discontinued
0.7727	Intermediate Similarity	NPD6797	Phase 2
0.7714	Intermediate Similarity	NPD7286	Phase 2
0.7684	Intermediate Similarity	NPD7251	Discontinued
0.7674	Intermediate Similarity	NPD6959	Discontinued
0.7673	Intermediate Similarity	NPD7033	Discontinued
0.7673	Intermediate Similarity	NPD3748	Approved
0.7657	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7808	Phase 3
0.7627	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6832	Phase 2
0.7607	Intermediate Similarity	NPD2309	Approved
0.7605	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5124	Phase 1
0.7542	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2424	Discontinued
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7527	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1652	Phase 2
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD447	Suspended
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7451	Intermediate Similarity	NPD9717	Approved
0.7429	Intermediate Similarity	NPD6808	Phase 2
0.7429	Intermediate Similarity	NPD5711	Approved
0.7429	Intermediate Similarity	NPD5710	Approved
0.7429	Intermediate Similarity	NPD7229	Phase 3
0.7427	Intermediate Similarity	NPD5761	Phase 2
0.7427	Intermediate Similarity	NPD5760	Phase 2
0.7419	Intermediate Similarity	NPD1203	Approved
0.7391	Intermediate Similarity	NPD4287	Approved
0.7375	Intermediate Similarity	NPD6355	Discontinued
0.7375	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD230	Phase 1
0.7371	Intermediate Similarity	NPD7199	Phase 2
0.736	Intermediate Similarity	NPD3751	Discontinued
0.7356	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4308	Phase 3
0.733	Intermediate Similarity	NPD3787	Discontinued
0.7329	Intermediate Similarity	NPD6651	Approved
0.7326	Intermediate Similarity	NPD8455	Phase 2
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8313	Approved
0.7308	Intermediate Similarity	NPD8312	Approved
0.7297	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6798	Discontinued
0.7296	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7268	Intermediate Similarity	NPD7584	Approved
0.7267	Intermediate Similarity	NPD37	Approved
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1019	Discontinued
0.7256	Intermediate Similarity	NPD6005	Phase 3
0.7256	Intermediate Similarity	NPD6004	Phase 3
0.7256	Intermediate Similarity	NPD6002	Phase 3
0.7256	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD2403	Approved
0.7241	Intermediate Similarity	NPD4965	Approved
0.7241	Intermediate Similarity	NPD4966	Approved
0.7241	Intermediate Similarity	NPD4967	Phase 2
0.7229	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5049	Phase 3
0.7205	Intermediate Similarity	NPD4307	Phase 2
0.7205	Intermediate Similarity	NPD943	Approved
0.7198	Intermediate Similarity	NPD6765	Approved
0.7198	Intermediate Similarity	NPD6764	Approved
0.7197	Intermediate Similarity	NPD2797	Approved
0.7193	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7191	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1296	Phase 2
0.7186	Intermediate Similarity	NPD3887	Approved
0.7186	Intermediate Similarity	NPD2354	Approved
0.7182	Intermediate Similarity	NPD1729	Discontinued
0.7179	Intermediate Similarity	NPD7583	Approved
0.7169	Intermediate Similarity	NPD2654	Approved
0.7168	Intermediate Similarity	NPD6280	Approved
0.7168	Intermediate Similarity	NPD6279	Approved
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1933	Approved
0.7159	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7152	Intermediate Similarity	NPD2798	Approved
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD7585	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1653	Approved
0.7121	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7783	Phase 2
0.7118	Intermediate Similarity	NPD6273	Approved
0.7113	Intermediate Similarity	NPD7435	Discontinued
0.7107	Intermediate Similarity	NPD8151	Discontinued
0.7105	Intermediate Similarity	NPD4361	Phase 2
0.7105	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8150	Discontinued
0.7089	Intermediate Similarity	NPD3266	Approved
0.7089	Intermediate Similarity	NPD3267	Approved
0.7086	Intermediate Similarity	NPD2296	Approved
0.7083	Intermediate Similarity	NPD6190	Approved
0.7081	Intermediate Similarity	NPD411	Approved
0.7081	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD4662	Approved
0.7059	Intermediate Similarity	NPD4661	Approved
0.7047	Intermediate Similarity	NPD6777	Approved
0.7047	Intermediate Similarity	NPD6776	Approved
0.7047	Intermediate Similarity	NPD6780	Approved
0.7047	Intermediate Similarity	NPD6778	Approved
0.7047	Intermediate Similarity	NPD6781	Approved
0.7047	Intermediate Similarity	NPD6782	Approved
0.7047	Intermediate Similarity	NPD6779	Approved
0.7044	Intermediate Similarity	NPD5647	Approved
0.7043	Intermediate Similarity	NPD6785	Approved
0.7043	Intermediate Similarity	NPD6784	Approved
0.703	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3225	Approved
0.7013	Intermediate Similarity	NPD9545	Approved
0.7011	Intermediate Similarity	NPD7685	Pre-registration
0.7011	Intermediate Similarity	NPD5889	Approved
0.7011	Intermediate Similarity	NPD5890	Approved
0.7006	Intermediate Similarity	NPD1608	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