NPASS Compound

Structure

CID49009 OpenBabel06191715382D 27 29 0 0 1 0 0 0 0 0999 V2000 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 6.0622 3.5000 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 3.4641 3.0000 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 2.5981 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 4.3301 3.5000 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 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 6.9282 3.0000 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 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 7.7942 4.5000 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 13 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 6 1 0 0 0 0 4 13 1 0 0 0 0 5 7 2 0 0 0 0 5 14 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 13 2 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 26 1 0 0 0 0 11 25 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 14 17 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 25 1 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 6 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	380.389
LogP:	3.101
LogD:	2.835
LogS:	-3.553
# Rotatable Bonds:	7
TPSA:	93.04
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	3.441
Fsp3:	0.381
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:	-4.865
MDCK Permeability:	1.5601239283569157e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.08
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	94.63067626953125%
Volume Distribution (VD):	0.39
Pgp-substrate:	6.586758136749268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.787
CYP2C19-inhibitor:	0.471
CYP2C19-substrate:	0.119
CYP2C9-inhibitor:	0.667
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.511
CYP2D6-substrate:	0.805
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	9.834
Half-life (T1/2):	0.249

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.177
Carcinogencity:	0.207
Eye Corrosion:	0.003
Eye Irritation:	0.07
Respiratory Toxicity:	0.317

Download Data

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

Natural Product: NPC49009

Natural Product ID:	NPC49009
*Common Name:**	6',7'-Dihydroxybergamottin
IUPAC Name:	4-[(E,6R)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-one
Synonyms:	6',7'-Dihydroxybergamottin
Standard InCHIKey:	IXZUPBUEKFXTSD-INMULRNOSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8+/t18-/m1/s1
SMILES:	C/C(=CCOc1c2ccc(=O)oc2cc2c1cco2)/CC[C@H](C(C)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079119
PubChem CID:	12082365
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	3
Others	7

Activity Type	# Activity
Cell Line	3
Individual Protein	5
ORGANISM	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	1580.0	nM	PMID[514078]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	810.0	nM	PMID[514080]
NPT1631	Individual Protein	Solute carrier organic anion transporter family member 1A5	Rattus norvegicus	Activity	=	22.0	%	PMID[514082]
NPT2107	Cell Line	PSN1	Homo sapiens	PC50	=	76.1	uM	PMID[514085]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	PC50	=	49.4	uM	PMID[514085]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	76.5	uM	PMID[514085]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	15400.0	nM	PMID[514079]
NPT26813	ORGANISM	Geotrichum	Geotrichum	Drug metabolism	>	49.0	%	PMID[514080]
NPT27	Others	Unspecified		Drug metabolism	>	49.0	%	PMID[514080]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	EC200	=	0.04	uM	PMID[514083]

☑ 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 NPC49009 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	352
0.1-0.2	1497
0.2-0.3	3664
0.3-0.4	8475
0.4-0.5	10425
0.5-0.6	4280
0.6-0.7	5903
0.7-0.8	5301
0.8-0.85	2109
0.85-0.9	542
0.9-0.95	138
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC14822
0.9868	High Similarity	NPC239270
0.9868	High Similarity	NPC303210
0.9868	High Similarity	NPC95472
0.9739	High Similarity	NPC169
0.9737	High Similarity	NPC269495
0.947	High Similarity	NPC191104
0.9404	High Similarity	NPC88445
0.9351	High Similarity	NPC278010
0.9351	High Similarity	NPC250769
0.9351	High Similarity	NPC295608
0.9286	High Similarity	NPC131725
0.9272	High Similarity	NPC304443
0.9272	High Similarity	NPC74539
0.9264	High Similarity	NPC325176
0.9255	High Similarity	NPC51404
0.9231	High Similarity	NPC270044
0.9216	High Similarity	NPC155882
0.9202	High Similarity	NPC224165
0.9146	High Similarity	NPC107244
0.9139	High Similarity	NPC246903
0.9103	High Similarity	NPC108937
0.9103	High Similarity	NPC279218
0.9085	High Similarity	NPC53917
0.9085	High Similarity	NPC266743
0.908	High Similarity	NPC472584
0.9051	High Similarity	NPC476349
0.9051	High Similarity	NPC476350
0.9045	High Similarity	NPC321372
0.9045	High Similarity	NPC474738
0.9045	High Similarity	NPC474609
0.9045	High Similarity	NPC129053
0.9045	High Similarity	NPC78554
0.9045	High Similarity	NPC109967
0.9045	High Similarity	NPC475797
0.9045	High Similarity	NPC469936
0.9032	High Similarity	NPC474772
0.9032	High Similarity	NPC472423
0.9032	High Similarity	NPC474744
0.9018	High Similarity	NPC120220
0.9013	High Similarity	NPC208584
0.9007	High Similarity	NPC51146
0.9007	High Similarity	NPC166858
0.9007	High Similarity	NPC313036
0.9006	High Similarity	NPC329215
0.9006	High Similarity	NPC259007
0.9006	High Similarity	NPC204088
0.8987	High Similarity	NPC260902
0.8987	High Similarity	NPC296957
0.8974	High Similarity	NPC256141
0.8974	High Similarity	NPC476238
0.8974	High Similarity	NPC263676
0.8974	High Similarity	NPC285623
0.8974	High Similarity	NPC31627
0.8974	High Similarity	NPC327269
0.8968	High Similarity	NPC472421
0.8968	High Similarity	NPC470908
0.8954	High Similarity	NPC190572
0.8951	High Similarity	NPC323137
0.8938	High Similarity	NPC45124
0.8938	High Similarity	NPC74854
0.8938	High Similarity	NPC30655
0.8924	High Similarity	NPC247677
0.8924	High Similarity	NPC160015
0.8917	High Similarity	NPC122365
0.891	High Similarity	NPC290671
0.891	High Similarity	NPC471675
0.8909	High Similarity	NPC233956
0.8903	High Similarity	NPC296030
0.8903	High Similarity	NPC37226
0.8903	High Similarity	NPC226644
0.8903	High Similarity	NPC317492
0.8903	High Similarity	NPC39929
0.8896	High Similarity	NPC202494
0.8889	High Similarity	NPC136641
0.8882	High Similarity	NPC219861
0.8875	High Similarity	NPC260296
0.8875	High Similarity	NPC304839
0.8875	High Similarity	NPC220582
0.8875	High Similarity	NPC115432
0.8874	High Similarity	NPC470856
0.8868	High Similarity	NPC65504
0.8861	High Similarity	NPC477530
0.8861	High Similarity	NPC474542
0.8854	High Similarity	NPC473996
0.8846	High Similarity	NPC180351
0.8846	High Similarity	NPC321387
0.8846	High Similarity	NPC327059
0.8846	High Similarity	NPC474735
0.8846	High Similarity	NPC148423
0.8846	High Similarity	NPC135303
0.8839	High Similarity	NPC168085
0.8834	High Similarity	NPC67450
0.8834	High Similarity	NPC155264
0.8834	High Similarity	NPC193881
0.8834	High Similarity	NPC210460
0.8831	High Similarity	NPC474302
0.8827	High Similarity	NPC472581
0.8827	High Similarity	NPC155640
0.882	High Similarity	NPC92589
0.882	High Similarity	NPC216092
0.8816	High Similarity	NPC254010
0.8812	High Similarity	NPC244750
0.8808	High Similarity	NPC262635
0.8805	High Similarity	NPC470625
0.8805	High Similarity	NPC19860
0.8797	High Similarity	NPC472583
0.8797	High Similarity	NPC1477
0.8797	High Similarity	NPC213608
0.8797	High Similarity	NPC223701
0.8797	High Similarity	NPC469405
0.8797	High Similarity	NPC7989
0.8797	High Similarity	NPC472462
0.879	High Similarity	NPC116604
0.879	High Similarity	NPC472580
0.879	High Similarity	NPC170169
0.879	High Similarity	NPC263384
0.879	High Similarity	NPC471676
0.879	High Similarity	NPC472636
0.879	High Similarity	NPC472422
0.879	High Similarity	NPC244577
0.879	High Similarity	NPC472420
0.8788	High Similarity	NPC144288
0.8788	High Similarity	NPC281835
0.8782	High Similarity	NPC37208
0.8782	High Similarity	NPC221868
0.878	High Similarity	NPC476459
0.8774	High Similarity	NPC285748
0.8774	High Similarity	NPC130581
0.8774	High Similarity	NPC222298
0.8774	High Similarity	NPC51070
0.8774	High Similarity	NPC198427
0.8774	High Similarity	NPC14875
0.8774	High Similarity	NPC12148
0.8773	High Similarity	NPC173149
0.8773	High Similarity	NPC179015
0.8766	High Similarity	NPC171656
0.8766	High Similarity	NPC297788
0.8758	High Similarity	NPC294432
0.8758	High Similarity	NPC243509
0.8742	High Similarity	NPC198490
0.8742	High Similarity	NPC470681
0.8742	High Similarity	NPC469934
0.8734	High Similarity	NPC67654
0.8734	High Similarity	NPC38361
0.8734	High Similarity	NPC130015
0.8734	High Similarity	NPC477957
0.8734	High Similarity	NPC5871
0.8726	High Similarity	NPC61258
0.8726	High Similarity	NPC78335
0.8726	High Similarity	NPC472406
0.8726	High Similarity	NPC230713
0.872	High Similarity	NPC53640
0.8718	High Similarity	NPC306788
0.8718	High Similarity	NPC272194
0.8718	High Similarity	NPC135325
0.8712	High Similarity	NPC179464
0.8712	High Similarity	NPC15819
0.871	High Similarity	NPC210826
0.871	High Similarity	NPC51641
0.871	High Similarity	NPC300267
0.871	High Similarity	NPC316769
0.8701	High Similarity	NPC184738
0.8701	High Similarity	NPC96216
0.8701	High Similarity	NPC17262
0.8701	High Similarity	NPC474939
0.8701	High Similarity	NPC470909
0.8701	High Similarity	NPC33653
0.8696	High Similarity	NPC40583
0.8696	High Similarity	NPC33320
0.8688	High Similarity	NPC17521
0.8684	High Similarity	NPC472515
0.8679	High Similarity	NPC41719
0.8679	High Similarity	NPC183874
0.8675	High Similarity	NPC253616
0.8671	High Similarity	NPC98028
0.8671	High Similarity	NPC156244
0.8671	High Similarity	NPC471677
0.8671	High Similarity	NPC472407
0.8667	High Similarity	NPC320789
0.8662	High Similarity	NPC164299
0.8662	High Similarity	NPC5173
0.8662	High Similarity	NPC178202
0.8659	High Similarity	NPC38914
0.8654	High Similarity	NPC91902
0.8654	High Similarity	NPC473133
0.8654	High Similarity	NPC85773
0.8654	High Similarity	NPC472627
0.8654	High Similarity	NPC47388
0.8654	High Similarity	NPC470670
0.865	High Similarity	NPC234536
0.865	High Similarity	NPC78612
0.865	High Similarity	NPC193998
0.8645	High Similarity	NPC316535
0.8645	High Similarity	NPC294365
0.8645	High Similarity	NPC133060
0.8645	High Similarity	NPC469953
0.8645	High Similarity	NPC311741
0.8645	High Similarity	NPC224714
0.8645	High Similarity	NPC470554

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 NPC49009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	883
0.2-0.3	1797
0.3-0.4	2587
0.4-0.5	2028
0.5-0.6	1032
0.6-0.7	358
0.7-0.8	117
0.8-0.85	31
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9272	High Similarity	NPD920	Approved
0.9139	High Similarity	NPD642	Clinical (unspecified phase)
0.9007	High Similarity	NPD643	Clinical (unspecified phase)
0.8808	High Similarity	NPD1243	Approved
0.8696	High Similarity	NPD919	Approved
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8616	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD6559	Discontinued
0.8519	High Similarity	NPD7075	Discontinued
0.8491	Intermediate Similarity	NPD4380	Phase 2
0.8462	Intermediate Similarity	NPD6799	Approved
0.8408	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD3749	Approved
0.8366	Intermediate Similarity	NPD2796	Approved
0.8364	Intermediate Similarity	NPD1247	Approved
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD7411	Suspended
0.8293	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6599	Discontinued
0.8225	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3817	Phase 2
0.8141	Intermediate Similarity	NPD1549	Phase 2
0.8121	Intermediate Similarity	NPD3882	Suspended
0.8084	Intermediate Similarity	NPD5494	Approved
0.8077	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD5403	Approved
0.807	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1510	Phase 2
0.8063	Intermediate Similarity	NPD2534	Approved
0.8063	Intermediate Similarity	NPD5401	Approved
0.8063	Intermediate Similarity	NPD2532	Approved
0.8063	Intermediate Similarity	NPD2533	Approved
0.8061	Intermediate Similarity	NPD5402	Approved
0.8049	Intermediate Similarity	NPD1934	Approved
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.8012	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2801	Approved
0.7975	Intermediate Similarity	NPD2800	Approved
0.7975	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD5844	Phase 1
0.7952	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2799	Discontinued
0.7925	Intermediate Similarity	NPD4628	Phase 3
0.7925	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1240	Approved
0.791	Intermediate Similarity	NPD8434	Phase 2
0.7908	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2313	Discontinued
0.7904	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1511	Approved
0.7848	Intermediate Similarity	NPD2344	Approved
0.7821	Intermediate Similarity	NPD1607	Approved
0.7812	Intermediate Similarity	NPD3750	Approved
0.7799	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6166	Phase 2
0.7791	Intermediate Similarity	NPD1512	Approved
0.7791	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD5953	Discontinued
0.7759	Intermediate Similarity	NPD7054	Approved
0.7759	Intermediate Similarity	NPD7286	Phase 2
0.7746	Intermediate Similarity	NPD7473	Discontinued
0.7733	Intermediate Similarity	NPD3926	Phase 2
0.7722	Intermediate Similarity	NPD3748	Approved
0.7722	Intermediate Similarity	NPD7033	Discontinued
0.7719	Intermediate Similarity	NPD6959	Discontinued
0.7714	Intermediate Similarity	NPD7472	Approved
0.7714	Intermediate Similarity	NPD7074	Phase 3
0.7701	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6797	Phase 2
0.7662	Intermediate Similarity	NPD6832	Phase 2
0.7654	Intermediate Similarity	NPD2309	Approved
0.7651	Intermediate Similarity	NPD3226	Approved
0.7643	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5124	Phase 1
0.7627	Intermediate Similarity	NPD7251	Discontinued
0.7584	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7808	Phase 3
0.7571	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.7473	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7471	Intermediate Similarity	NPD1465	Phase 2
0.7471	Intermediate Similarity	NPD6808	Phase 2
0.7471	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD5760	Phase 2
0.7471	Intermediate Similarity	NPD5711	Approved
0.7471	Intermediate Similarity	NPD5761	Phase 2
0.7469	Intermediate Similarity	NPD2424	Discontinued
0.7468	Intermediate Similarity	NPD1203	Approved
0.7446	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4287	Approved
0.7425	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1652	Phase 2
0.7421	Intermediate Similarity	NPD447	Suspended
0.7421	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD230	Phase 1
0.7391	Intermediate Similarity	NPD4308	Phase 3
0.7375	Intermediate Similarity	NPD6651	Approved
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3268	Approved
0.732	Intermediate Similarity	NPD422	Phase 1
0.7314	Intermediate Similarity	NPD7199	Phase 2
0.7312	Intermediate Similarity	NPD6355	Discontinued
0.7308	Intermediate Similarity	NPD1019	Discontinued
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7301	Intermediate Similarity	NPD6004	Phase 3
0.7301	Intermediate Similarity	NPD6005	Phase 3
0.7301	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6002	Phase 3
0.7301	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7253	Intermediate Similarity	NPD8312	Approved
0.7253	Intermediate Similarity	NPD8313	Approved
0.725	Intermediate Similarity	NPD943	Approved
0.725	Intermediate Similarity	NPD4307	Phase 2
0.7244	Intermediate Similarity	NPD2797	Approved
0.7243	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1296	Phase 2
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD1729	Discontinued
0.7216	Intermediate Similarity	NPD7584	Approved
0.7212	Intermediate Similarity	NPD2654	Approved
0.7209	Intermediate Similarity	NPD37	Approved
0.7209	Intermediate Similarity	NPD6280	Approved
0.7209	Intermediate Similarity	NPD6279	Approved
0.7208	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2798	Approved
0.7195	Intermediate Similarity	NPD1471	Phase 3
0.7191	Intermediate Similarity	NPD2403	Approved
0.7184	Intermediate Similarity	NPD4966	Approved
0.7184	Intermediate Similarity	NPD4967	Phase 2
0.7184	Intermediate Similarity	NPD4965	Approved
0.7181	Intermediate Similarity	NPD4360	Phase 2
0.7181	Intermediate Similarity	NPD4363	Phase 3
0.716	Intermediate Similarity	NPD5049	Phase 3
0.716	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD6764	Approved
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7143	Intermediate Similarity	NPD6765	Approved
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3266	Approved
0.7134	Intermediate Similarity	NPD3267	Approved
0.7128	Intermediate Similarity	NPD7583	Approved
0.7126	Intermediate Similarity	NPD2354	Approved
0.7126	Intermediate Similarity	NPD2296	Approved
0.7126	Intermediate Similarity	NPD3887	Approved
0.7125	Intermediate Similarity	NPD411	Approved
0.7125	Intermediate Similarity	NPD3764	Approved
0.7125	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6234	Discontinued
0.7099	Intermediate Similarity	NPD1933	Approved
0.7095	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7585	Approved
0.7081	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6233	Phase 2
0.7076	Intermediate Similarity	NPD1653	Approved
0.7073	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7783	Phase 2
0.707	Intermediate Similarity	NPD3225	Approved
0.7062	Intermediate Similarity	NPD7435	Discontinued
0.7059	Intermediate Similarity	NPD9545	Approved
0.7056	Intermediate Similarity	NPD8151	Discontinued
0.7052	Intermediate Similarity	NPD5890	Approved
0.7052	Intermediate Similarity	NPD5889	Approved
0.7051	Intermediate Similarity	NPD1608	Approved
0.7043	Intermediate Similarity	NPD8150	Discontinued
0.7041	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4288	Approved
0.7024	Intermediate Similarity	NPD6190	Approved
0.7019	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6844	Discontinued
0.7	Intermediate Similarity	NPD4661	Approved
0.7	Intermediate Similarity	NPD4662	Approved
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6994	Remote Similarity	NPD6585	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