NPASS Compound

Structure

NPC205361 OpenBabel07101718322D 29 31 0 0 1 0 0 0 0 0999 V2000 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 3.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8301 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 0.8660 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 20 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 9 21 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 27 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 25 1 0 0 0 0 14 21 1 0 0 0 0 14 22 1 6 0 0 0 15 8 1 6 0 0 0 15 20 1 0 0 0 0 15 29 1 0 0 0 0 16 23 2 0 0 0 0 16 28 1 0 0 0 0 17 19 2 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 0 0 0 0 19 26 1 0 0 0 0 20 29 1 0 0 0 0 21 3 1 6 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.18
Volume:	403.242
LogP:	1.975
LogD:	1.808
LogS:	-3.962
# Rotatable Bonds:	9
TPSA:	110.89
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	3.956
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.773
MDCK Permeability:	2.3201455405796878e-05
Pgp-inhibitor:	0.595
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.226
Plasma Protein Binding (PPB):	73.93882751464844%
Volume Distribution (VD):	0.815
Pgp-substrate:	16.701845169067383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.42
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.747
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.652
CYP2D6-inhibitor:	0.1
CYP2D6-substrate:	0.602
CYP3A4-inhibitor:	0.112
CYP3A4-substrate:	0.431

ADMET: Excretion

Clearance (CL):	7.644
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.83
Drug-inuced Liver Injury (DILI):	0.701
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.816
Skin Sensitization:	0.272
Carcinogencity:	0.184
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.087

Download Data

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

Natural Product: NPC205361

Natural Product ID:	NPC205361
*Common Name:**	Altissimacoumarin E
IUPAC Name:	7-[(2R,3R)-5-[(2R)-3,3-dimethyloxiran-2-yl]-2,3-dihydroxy-3-methylpentoxy]-6,8-dimethoxychromen-2-one
Synonyms:	Altissimacoumarin E
Standard InCHIKey:	BANQKNDBYSHYOO-VTJXTGGHSA-N
Standard InCHI:	InChI=1S/C21H28O8/c1-20(2)15(29-20)8-9-21(3,24)14(22)11-27-18-13(25-4)10-12-6-7-16(23)28-17(12)19(18)26-5/h6-7,10,14-15,22,24H,8-9,11H2,1-5H3/t14-,15-,21-/m1/s1
SMILES:	COc1cc2ccc(=O)oc2c(c1OC[C@H]([C@@](CC[C@H]1OC1(C)C)(O)C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071527
PubChem CID:	60201875
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	Activity	>	50.0	%	PMID[547103]

☑ 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 NPC205361 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	404
0.1-0.2	1741
0.2-0.3	4708
0.3-0.4	9995
0.4-0.5	8023
0.5-0.6	4328
0.6-0.7	5817
0.7-0.8	5412
0.8-0.85	1913
0.85-0.9	325
0.9-0.95	27
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC138212
0.9638	High Similarity	NPC300611
0.9371	High Similarity	NPC15577
0.9357	High Similarity	NPC472520
0.9357	High Similarity	NPC279851
0.9353	High Similarity	NPC164148
0.9353	High Similarity	NPC43500
0.9178	High Similarity	NPC205727
0.9178	High Similarity	NPC120426
0.9178	High Similarity	NPC294522
0.9178	High Similarity	NPC21184
0.9172	High Similarity	NPC96294
0.9161	High Similarity	NPC471763
0.913	High Similarity	NPC36437
0.913	High Similarity	NPC241341
0.913	High Similarity	NPC233018
0.911	High Similarity	NPC30688
0.911	High Similarity	NPC176903
0.9097	High Similarity	NPC476450
0.9078	High Similarity	NPC13067
0.9058	High Similarity	NPC319969
0.9058	High Similarity	NPC137669
0.9048	High Similarity	NPC114740
0.9041	High Similarity	NPC476348
0.9041	High Similarity	NPC187398
0.9007	High Similarity	NPC95162
0.9007	High Similarity	NPC52086
0.9007	High Similarity	NPC139548
0.9007	High Similarity	NPC148835
0.9007	High Similarity	NPC155963
0.9007	High Similarity	NPC20511
0.9007	High Similarity	NPC76336
0.9	High Similarity	NPC472525
0.8986	High Similarity	NPC213197
0.8986	High Similarity	NPC29734
0.8973	High Similarity	NPC476347
0.8958	High Similarity	NPC7439
0.8958	High Similarity	NPC34245
0.8958	High Similarity	NPC110067
0.8958	High Similarity	NPC256555
0.8958	High Similarity	NPC91492
0.8944	High Similarity	NPC270256
0.8944	High Similarity	NPC151946
0.8936	High Similarity	NPC126682
0.8936	High Similarity	NPC286843
0.8936	High Similarity	NPC38099
0.8936	High Similarity	NPC82271
0.8936	High Similarity	NPC26954
0.8929	High Similarity	NPC224475
0.8929	High Similarity	NPC309953
0.8929	High Similarity	NPC180716
0.8929	High Similarity	NPC62366
0.8929	High Similarity	NPC213173
0.8926	High Similarity	NPC264875
0.8926	High Similarity	NPC120774
0.8926	High Similarity	NPC470264
0.8926	High Similarity	NPC163598
0.8913	High Similarity	NPC19242
0.8913	High Similarity	NPC113098
0.8913	High Similarity	NPC240722
0.8913	High Similarity	NPC244799
0.8912	High Similarity	NPC93924
0.8889	High Similarity	NPC469564
0.8881	High Similarity	NPC312881
0.8873	High Similarity	NPC153818
0.8873	High Similarity	NPC232246
0.8865	High Similarity	NPC234865
0.8865	High Similarity	NPC472521
0.8857	High Similarity	NPC472522
0.8851	High Similarity	NPC313334
0.8851	High Similarity	NPC206264
0.8851	High Similarity	NPC212670
0.8849	High Similarity	NPC272650
0.8849	High Similarity	NPC267336
0.8844	High Similarity	NPC52740
0.8841	High Similarity	NPC27239
0.8841	High Similarity	NPC123127
0.8828	High Similarity	NPC236419
0.8819	High Similarity	NPC287286
0.8819	High Similarity	NPC152771
0.8819	High Similarity	NPC195357
0.8811	High Similarity	NPC279573
0.8803	High Similarity	NPC188380
0.8803	High Similarity	NPC167517
0.8803	High Similarity	NPC78746
0.8803	High Similarity	NPC471719
0.8803	High Similarity	NPC224543
0.88	High Similarity	NPC215060
0.88	High Similarity	NPC476352
0.8794	High Similarity	NPC474600
0.8794	High Similarity	NPC92830
0.8794	High Similarity	NPC326600
0.8794	High Similarity	NPC204353
0.8794	High Similarity	NPC50896
0.8742	High Similarity	NPC150442
0.8741	High Similarity	NPC212124
0.8741	High Similarity	NPC225106
0.8741	High Similarity	NPC281014
0.8741	High Similarity	NPC184861
0.8741	High Similarity	NPC294456
0.8741	High Similarity	NPC476171
0.8732	High Similarity	NPC224941
0.8732	High Similarity	NPC469675
0.8732	High Similarity	NPC33986
0.8732	High Similarity	NPC311430
0.8723	High Similarity	NPC26673
0.8723	High Similarity	NPC31849
0.8723	High Similarity	NPC277021
0.8723	High Similarity	NPC469449
0.8716	High Similarity	NPC41844
0.8716	High Similarity	NPC178129
0.8707	High Similarity	NPC469701
0.8707	High Similarity	NPC85624
0.8699	High Similarity	NPC230157
0.8693	High Similarity	NPC284810
0.8684	High Similarity	NPC8712
0.8681	High Similarity	NPC211110
0.8675	High Similarity	NPC53587
0.8675	High Similarity	NPC169404
0.8675	High Similarity	NPC176186
0.8671	High Similarity	NPC472336
0.8671	High Similarity	NPC472334
0.8667	High Similarity	NPC477381
0.8662	High Similarity	NPC147030
0.8662	High Similarity	NPC309744
0.8662	High Similarity	NPC98179
0.8662	High Similarity	NPC253574
0.8658	High Similarity	NPC139839
0.8652	High Similarity	NPC5423
0.8652	High Similarity	NPC137949
0.8649	High Similarity	NPC268515
0.8649	High Similarity	NPC40222
0.8643	High Similarity	NPC80170
0.8643	High Similarity	NPC476399
0.8639	High Similarity	NPC471824
0.8633	High Similarity	NPC474616
0.8621	High Similarity	NPC267291
0.8618	High Similarity	NPC149735
0.8611	High Similarity	NPC474886
0.8611	High Similarity	NPC471069
0.8611	High Similarity	NPC471068
0.8611	High Similarity	NPC20796
0.8611	High Similarity	NPC38874
0.8609	High Similarity	NPC477379
0.8601	High Similarity	NPC472337
0.8592	High Similarity	NPC296624
0.8592	High Similarity	NPC207002
0.8592	High Similarity	NPC471910
0.8592	High Similarity	NPC474810
0.8592	High Similarity	NPC133956
0.8592	High Similarity	NPC167111
0.8592	High Similarity	NPC263064
0.8592	High Similarity	NPC318400
0.8591	High Similarity	NPC183083
0.8591	High Similarity	NPC231149
0.8591	High Similarity	NPC471764
0.8591	High Similarity	NPC87950
0.8591	High Similarity	NPC296377
0.8591	High Similarity	NPC295297
0.8591	High Similarity	NPC137352
0.8582	High Similarity	NPC73738
0.8561	High Similarity	NPC474670
0.8561	High Similarity	NPC258567
0.8561	High Similarity	NPC121740
0.8561	High Similarity	NPC224774
0.8552	High Similarity	NPC471072
0.8552	High Similarity	NPC471070
0.8552	High Similarity	NPC471071
0.8551	High Similarity	NPC27352
0.8533	High Similarity	NPC48366
0.8533	High Similarity	NPC478237
0.8533	High Similarity	NPC169510
0.8531	High Similarity	NPC310854
0.8531	High Similarity	NPC195343
0.8531	High Similarity	NPC84894
0.8531	High Similarity	NPC111635
0.8531	High Similarity	NPC267412
0.8531	High Similarity	NPC319859
0.8531	High Similarity	NPC164269
0.8531	High Similarity	NPC18804
0.8531	High Similarity	NPC166672
0.8531	High Similarity	NPC287182
0.8531	High Similarity	NPC47163
0.8531	High Similarity	NPC260265
0.8531	High Similarity	NPC198381
0.8531	High Similarity	NPC127888
0.8531	High Similarity	NPC74655
0.8531	High Similarity	NPC307412
0.8531	High Similarity	NPC100986
0.8531	High Similarity	NPC55149
0.8531	High Similarity	NPC135127
0.8521	High Similarity	NPC245120
0.8521	High Similarity	NPC194277
0.8521	High Similarity	NPC14248
0.8521	High Similarity	NPC123954
0.8511	High Similarity	NPC79184
0.8511	High Similarity	NPC307042
0.8511	High Similarity	NPC474617
0.8506	High Similarity	NPC155015
0.8506	High Similarity	NPC142479

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 NPC205361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	978
0.2-0.3	2133
0.3-0.4	2600
0.4-0.5	1727
0.5-0.6	897
0.6-0.7	327
0.7-0.8	97
0.8-0.85	28
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8851	High Similarity	NPD1653	Approved
0.8188	Intermediate Similarity	NPD1652	Phase 2
0.8182	Intermediate Similarity	NPD3027	Phase 3
0.8138	Intermediate Similarity	NPD1613	Approved
0.8138	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD5124	Phase 1
0.8082	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5844	Phase 1
0.8038	Intermediate Similarity	NPD3817	Phase 2
0.8	Intermediate Similarity	NPD422	Phase 1
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2801	Approved
0.7862	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7549	Discontinued
0.7812	Intermediate Similarity	NPD5402	Approved
0.7799	Intermediate Similarity	NPD1934	Approved
0.7793	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3818	Discontinued
0.7756	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7199	Phase 2
0.7676	Intermediate Similarity	NPD3496	Discontinued
0.7651	Intermediate Similarity	NPD6166	Phase 2
0.7651	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7054	Approved
0.7582	Intermediate Similarity	NPD7266	Discontinued
0.7578	Intermediate Similarity	NPD37	Approved
0.7578	Intermediate Similarity	NPD6801	Discontinued
0.7574	Intermediate Similarity	NPD7472	Approved
0.7574	Intermediate Similarity	NPD7074	Phase 3
0.7551	Intermediate Similarity	NPD3018	Phase 2
0.7546	Intermediate Similarity	NPD4965	Approved
0.7546	Intermediate Similarity	NPD4966	Approved
0.7546	Intermediate Similarity	NPD4967	Phase 2
0.7546	Intermediate Similarity	NPD3882	Suspended
0.7531	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6799	Approved
0.7515	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5403	Approved
0.7483	Intermediate Similarity	NPD447	Suspended
0.747	Intermediate Similarity	NPD8127	Discontinued
0.7468	Intermediate Similarity	NPD5401	Approved
0.7455	Intermediate Similarity	NPD919	Approved
0.7455	Intermediate Similarity	NPD6234	Discontinued
0.7453	Intermediate Similarity	NPD4380	Phase 2
0.7442	Intermediate Similarity	NPD7808	Phase 3
0.7436	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7427	Intermediate Similarity	NPD6797	Phase 2
0.7423	Intermediate Similarity	NPD7819	Suspended
0.7419	Intermediate Similarity	NPD2424	Discontinued
0.7417	Intermediate Similarity	NPD4060	Phase 1
0.7405	Intermediate Similarity	NPD1511	Approved
0.7397	Intermediate Similarity	NPD2982	Phase 2
0.7397	Intermediate Similarity	NPD2983	Phase 2
0.7384	Intermediate Similarity	NPD7251	Discontinued
0.7383	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4908	Phase 1
0.7379	Intermediate Similarity	NPD1091	Approved
0.7375	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7355	Intermediate Similarity	NPD5763	Approved
0.7355	Intermediate Similarity	NPD5762	Approved
0.7351	Intermediate Similarity	NPD6233	Phase 2
0.7346	Intermediate Similarity	NPD6599	Discontinued
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7329	Intermediate Similarity	NPD3686	Approved
0.7329	Intermediate Similarity	NPD3687	Approved
0.7329	Intermediate Similarity	NPD2981	Phase 2
0.7325	Intermediate Similarity	NPD3750	Approved
0.7321	Intermediate Similarity	NPD6232	Discontinued
0.7315	Intermediate Similarity	NPD2861	Phase 2
0.7312	Intermediate Similarity	NPD1512	Approved
0.729	Intermediate Similarity	NPD2796	Approved
0.729	Intermediate Similarity	NPD2935	Discontinued
0.7289	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7843	Approved
0.7285	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1296	Phase 2
0.7285	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6798	Discontinued
0.7283	Intermediate Similarity	NPD6559	Discontinued
0.7279	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4749	Approved
0.7262	Intermediate Similarity	NPD1247	Approved
0.7261	Intermediate Similarity	NPD6674	Discontinued
0.726	Intermediate Similarity	NPD1610	Phase 2
0.7255	Intermediate Similarity	NPD6355	Discontinued
0.7254	Intermediate Similarity	NPD7157	Approved
0.7254	Intermediate Similarity	NPD6671	Approved
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.7251	Intermediate Similarity	NPD7228	Approved
0.7246	Intermediate Similarity	NPD2684	Approved
0.7232	Intermediate Similarity	NPD6843	Phase 3
0.7232	Intermediate Similarity	NPD6842	Approved
0.7232	Intermediate Similarity	NPD6841	Approved
0.7226	Intermediate Similarity	NPD7033	Discontinued
0.7226	Intermediate Similarity	NPD3748	Approved
0.7219	Intermediate Similarity	NPD7095	Approved
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7215	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4110	Phase 3
0.7197	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7411	Suspended
0.7193	Intermediate Similarity	NPD7473	Discontinued
0.7188	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7685	Pre-registration
0.7181	Intermediate Similarity	NPD2797	Approved
0.7174	Intermediate Similarity	NPD290	Approved
0.7174	Intermediate Similarity	NPD1358	Approved
0.7172	Intermediate Similarity	NPD5691	Approved
0.7161	Intermediate Similarity	NPD7097	Phase 1
0.7153	Intermediate Similarity	NPD5536	Phase 2
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD4340	Discontinued
0.7123	Intermediate Similarity	NPD1778	Approved
0.7123	Intermediate Similarity	NPD4626	Approved
0.7119	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8651	Approved
0.7114	Intermediate Similarity	NPD3225	Approved
0.7113	Intermediate Similarity	NPD5283	Phase 1
0.711	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4625	Phase 3
0.7097	Intermediate Similarity	NPD6653	Approved
0.7092	Intermediate Similarity	NPD228	Approved
0.7091	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1549	Phase 2
0.7086	Intermediate Similarity	NPD7240	Approved
0.7081	Intermediate Similarity	NPD4357	Discontinued
0.7078	Intermediate Similarity	NPD4140	Approved
0.707	Intermediate Similarity	NPD1551	Phase 2
0.707	Intermediate Similarity	NPD6032	Approved
0.7066	Intermediate Similarity	NPD5353	Approved
0.7066	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3268	Approved
0.7059	Intermediate Similarity	NPD7985	Registered
0.7055	Intermediate Similarity	NPD920	Approved
0.7044	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5535	Approved
0.7039	Intermediate Similarity	NPD6832	Phase 2
0.7037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD9697	Approved
0.7027	Intermediate Similarity	NPD1611	Approved
0.7025	Intermediate Similarity	NPD1375	Discontinued
0.7025	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3540	Phase 1
0.7025	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7768	Phase 2
0.702	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8455	Phase 2
0.7006	Intermediate Similarity	NPD1510	Phase 2
0.7006	Intermediate Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5090	Approved
0.6988	Remote Similarity	NPD5089	Approved
0.6978	Remote Similarity	NPD3134	Approved
0.6977	Remote Similarity	NPD5242	Approved
0.6977	Remote Similarity	NPD3926	Phase 2
0.697	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2415	Discontinued
0.6962	Remote Similarity	NPD3539	Phase 1
0.6957	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2677	Approved
0.6948	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4538	Approved
0.6943	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4536	Approved
0.6939	Remote Similarity	NPD1357	Approved
0.6937	Remote Similarity	NPD1243	Approved
0.6933	Remote Similarity	NPD2532	Approved
0.6933	Remote Similarity	NPD2534	Approved
0.6933	Remote Similarity	NPD2533	Approved
0.6933	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4678	Approved
0.6928	Remote Similarity	NPD4675	Approved
0.6923	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1933	Approved
0.6918	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6005	Phase 3
0.6918	Remote Similarity	NPD6004	Phase 3
0.6918	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6002	Phase 3
0.6914	Remote Similarity	NPD5058	Phase 3
0.6914	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4062	Phase 3

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