NPASS Compound

Structure

CID233018 OpenBabel06191716032D 26 27 0 0 0 0 0 0 0 0999 V2000 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 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 1.7321 -3.0000 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 -0.8660 -1.5000 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 -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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -1.7321 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 14 1 0 0 0 0 3 15 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 15 2 0 0 0 0 12 25 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 21 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	380.155
LogP:	4.56
LogD:	3.932
LogS:	-5.4
# Rotatable Bonds:	8
TPSA:	57.9
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	2.74
Fsp3:	0.381
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:	-4.66
MDCK Permeability:	1.6371857782360166e-05
Pgp-inhibitor:	0.611
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.075

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	86.43278503417969%
Volume Distribution (VD):	0.585
Pgp-substrate:	14.592315673828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.913
CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.582
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.697
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.662
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	10.737
Half-life (T1/2):	0.297

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.877
Drug-inuced Liver Injury (DILI):	0.692
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.716
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC233018

Natural Product ID:	NPC233018
*Common Name:**	Altissimacoumarin D
IUPAC Name:	7-[(2E)-3,7-dimethylocta-2,6-dienoxy]-6,8-dimethoxychromen-2-one
Synonyms:	Altissimacoumarin D
Standard InCHIKey:	GEBSUJHFARTCMC-RVDMUPIBSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-14(2)7-6-8-15(3)11-12-25-20-17(23-4)13-16-9-10-18(22)26-19(16)21(20)24-5/h7,9-11,13H,6,8,12H2,1-5H3/b15-11+
SMILES:	CC(=CCC/C(=C/COc1c(cc2ccc(=O)oc2c1OC)OC)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071526
PubChem CID:	60201874
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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[472662]

☑ 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 NPC233018 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	455
0.1-0.2	1923
0.2-0.3	5532
0.3-0.4	10621
0.4-0.5	6686
0.5-0.6	4037
0.6-0.7	5786
0.7-0.8	5294
0.8-0.85	1798
0.85-0.9	464
0.9-0.95	89
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC241341
1.0	High Similarity	NPC36437
0.9921	High Similarity	NPC137669
0.9764	High Similarity	NPC319969
0.9762	High Similarity	NPC19242
0.9762	High Similarity	NPC244799
0.9762	High Similarity	NPC240722
0.9683	High Similarity	NPC123127
0.9683	High Similarity	NPC27239
0.9618	High Similarity	NPC43500
0.9618	High Similarity	NPC164148
0.9612	High Similarity	NPC309953
0.9474	High Similarity	NPC300611
0.9466	High Similarity	NPC286843
0.9394	High Similarity	NPC20796
0.9389	High Similarity	NPC234865
0.9385	High Similarity	NPC472522
0.9333	High Similarity	NPC138212
0.9323	High Similarity	NPC13067
0.9323	High Similarity	NPC270256
0.9318	High Similarity	NPC167517
0.9313	High Similarity	NPC474600
0.9297	High Similarity	NPC474616
0.9291	High Similarity	NPC127604
0.9248	High Similarity	NPC20511
0.9248	High Similarity	NPC52086
0.9248	High Similarity	NPC148835
0.9248	High Similarity	NPC95162
0.9248	High Similarity	NPC139548
0.9248	High Similarity	NPC76336
0.9242	High Similarity	NPC240915
0.9219	High Similarity	NPC474670
0.9219	High Similarity	NPC194841
0.9173	High Similarity	NPC126682
0.9173	High Similarity	NPC82271
0.9167	High Similarity	NPC147030
0.9167	High Similarity	NPC7163
0.9154	High Similarity	NPC476399
0.9147	High Similarity	NPC474651
0.9147	High Similarity	NPC474623
0.913	High Similarity	NPC205361
0.9127	High Similarity	NPC288238
0.9098	High Similarity	NPC472521
0.9098	High Similarity	NPC73071
0.907	High Similarity	NPC474821
0.9065	High Similarity	NPC15577
0.9023	High Similarity	NPC92830
0.9015	High Similarity	NPC123954
0.9015	High Similarity	NPC5423
0.9	High Similarity	NPC210674
0.9	High Similarity	NPC96294
0.8992	High Similarity	NPC474632
0.8976	High Similarity	NPC194626
0.8968	High Similarity	NPC235190
0.8968	High Similarity	NPC180006
0.8968	High Similarity	NPC163200
0.8955	High Similarity	NPC311430
0.8955	High Similarity	NPC224941
0.8947	High Similarity	NPC26673
0.8936	High Similarity	NPC30688
0.8936	High Similarity	NPC176903
0.8921	High Similarity	NPC476450
0.8913	High Similarity	NPC110067
0.8913	High Similarity	NPC34245
0.8913	High Similarity	NPC7439
0.8913	High Similarity	NPC256555
0.8913	High Similarity	NPC91492
0.8906	High Similarity	NPC108545
0.8905	High Similarity	NPC279851
0.8905	High Similarity	NPC472520
0.8889	High Similarity	NPC222175
0.8873	High Similarity	NPC205727
0.8873	High Similarity	NPC21184
0.8873	High Similarity	NPC120426
0.8873	High Similarity	NPC294522
0.8873	High Similarity	NPC114740
0.8872	High Similarity	NPC245120
0.8872	High Similarity	NPC137949
0.8864	High Similarity	NPC474617
0.8864	High Similarity	NPC307042
0.8864	High Similarity	NPC79184
0.8855	High Similarity	NPC474636
0.8846	High Similarity	NPC101894
0.8824	High Similarity	NPC474521
0.8824	High Similarity	NPC474530
0.8824	High Similarity	NPC474540
0.8811	High Similarity	NPC213197
0.881	High Similarity	NPC281356
0.881	High Similarity	NPC298796
0.8806	High Similarity	NPC167111
0.8806	High Similarity	NPC471910
0.8806	High Similarity	NPC318400
0.8806	High Similarity	NPC207002
0.8806	High Similarity	NPC133956
0.8806	High Similarity	NPC277021
0.8806	High Similarity	NPC296624
0.8797	High Similarity	NPC73738
0.8794	High Similarity	NPC476347
0.8794	High Similarity	NPC178129
0.8794	High Similarity	NPC231149
0.8777	High Similarity	NPC236419
0.8769	High Similarity	NPC27352
0.876	High Similarity	NPC273772
0.876	High Similarity	NPC109675
0.875	High Similarity	NPC120774
0.875	High Similarity	NPC264875
0.875	High Similarity	NPC163598
0.8741	High Similarity	NPC267412
0.8741	High Similarity	NPC47163
0.8741	High Similarity	NPC111635
0.8741	High Similarity	NPC195343
0.8741	High Similarity	NPC74655
0.8741	High Similarity	NPC84894
0.8741	High Similarity	NPC164269
0.8741	High Similarity	NPC127888
0.8741	High Similarity	NPC287182
0.8741	High Similarity	NPC18804
0.8741	High Similarity	NPC198381
0.8741	High Similarity	NPC166672
0.8741	High Similarity	NPC100986
0.8741	High Similarity	NPC260265
0.8741	High Similarity	NPC307412
0.8741	High Similarity	NPC55149
0.8741	High Similarity	NPC319859
0.8732	High Similarity	NPC187398
0.8732	High Similarity	NPC476348
0.8732	High Similarity	NPC139839
0.8731	High Similarity	NPC14248
0.873	High Similarity	NPC152306
0.873	High Similarity	NPC265547
0.8714	High Similarity	NPC471763
0.8705	High Similarity	NPC469564
0.8692	High Similarity	NPC73413
0.8692	High Similarity	NPC27671
0.8692	High Similarity	NPC201667
0.8686	High Similarity	NPC476171
0.8676	High Similarity	NPC86892
0.8676	High Similarity	NPC471909
0.8676	High Similarity	NPC469675
0.8676	High Similarity	NPC281241
0.8676	High Similarity	NPC472424
0.8676	High Similarity	NPC471625
0.8672	High Similarity	NPC267064
0.8671	High Similarity	NPC212670
0.8671	High Similarity	NPC313334
0.8671	High Similarity	NPC206264
0.8667	High Similarity	NPC7526
0.8667	High Similarity	NPC474810
0.8667	High Similarity	NPC222036
0.8662	High Similarity	NPC52740
0.8661	High Similarity	NPC308217
0.8657	High Similarity	NPC29734
0.8651	High Similarity	NPC304208
0.8651	High Similarity	NPC52464
0.8647	High Similarity	NPC168710
0.8643	High Similarity	NPC230157
0.8636	High Similarity	NPC121740
0.8636	High Similarity	NPC258567
0.8636	High Similarity	NPC224774
0.863	High Similarity	NPC186507
0.8626	High Similarity	NPC471828
0.8626	High Similarity	NPC471827
0.8615	High Similarity	NPC279379
0.8615	High Similarity	NPC472518
0.8613	High Similarity	NPC128529
0.8613	High Similarity	NPC26954
0.8613	High Similarity	NPC476455
0.8613	High Similarity	NPC471630
0.8613	High Similarity	NPC160727
0.8613	High Similarity	NPC55615
0.8613	High Similarity	NPC283019
0.8613	High Similarity	NPC38099
0.8613	High Similarity	NPC149320
0.8613	High Similarity	NPC177281
0.8605	High Similarity	NPC310373
0.8603	High Similarity	NPC309744
0.8601	High Similarity	NPC48366
0.8601	High Similarity	NPC93924
0.8583	High Similarity	NPC96705
0.8582	High Similarity	NPC80170
0.8582	High Similarity	NPC185127
0.8582	High Similarity	NPC113098
0.8571	High Similarity	NPC469453
0.8571	High Similarity	NPC128633
0.8571	High Similarity	NPC31707
0.8571	High Similarity	NPC199204
0.8571	High Similarity	NPC109275
0.8571	High Similarity	NPC472519
0.8561	High Similarity	NPC244364
0.8551	High Similarity	NPC155963
0.8551	High Similarity	NPC474886
0.8551	High Similarity	NPC38874
0.854	High Similarity	NPC472525
0.8538	High Similarity	NPC248429
0.8538	High Similarity	NPC261661
0.8538	High Similarity	NPC270326
0.8538	High Similarity	NPC96286
0.8531	High Similarity	NPC41844
0.8529	High Similarity	NPC469449
0.8529	High Similarity	NPC31849

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 NPC233018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1016
0.2-0.3	2058
0.3-0.4	2609
0.4-0.5	1682
0.5-0.6	893
0.6-0.7	350
0.7-0.8	104
0.8-0.85	32
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8671	High Similarity	NPD1653	Approved
0.8182	Intermediate Similarity	NPD422	Phase 1
0.8151	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD3817	Phase 2
0.7986	Intermediate Similarity	NPD1652	Phase 2
0.797	Intermediate Similarity	NPD3496	Discontinued
0.7956	Intermediate Similarity	NPD3018	Phase 2
0.7899	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2801	Approved
0.7862	Intermediate Similarity	NPD5844	Phase 1
0.7857	Intermediate Similarity	NPD1358	Approved
0.7852	Intermediate Similarity	NPD2981	Phase 2
0.7842	Intermediate Similarity	NPD3027	Phase 3
0.7806	Intermediate Similarity	NPD919	Approved
0.7803	Intermediate Similarity	NPD5536	Phase 2
0.7801	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1613	Approved
0.7794	Intermediate Similarity	NPD2983	Phase 2
0.7794	Intermediate Similarity	NPD2982	Phase 2
0.7786	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7549	Discontinued
0.777	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5494	Approved
0.7746	Intermediate Similarity	NPD5124	Phase 1
0.7746	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD447	Suspended
0.7698	Intermediate Similarity	NPD9697	Approved
0.7698	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1296	Phase 2
0.7651	Intermediate Similarity	NPD6799	Approved
0.7647	Intermediate Similarity	NPD3705	Approved
0.7638	Intermediate Similarity	NPD3134	Approved
0.7616	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD5402	Approved
0.7597	Intermediate Similarity	NPD1934	Approved
0.7595	Intermediate Similarity	NPD1247	Approved
0.7586	Intermediate Similarity	NPD3748	Approved
0.7564	Intermediate Similarity	NPD3882	Suspended
0.7556	Intermediate Similarity	NPD5691	Approved
0.7534	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD5353	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7481	Intermediate Similarity	NPD1548	Phase 1
0.7455	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD5535	Approved
0.7421	Intermediate Similarity	NPD5677	Discontinued
0.7417	Intermediate Similarity	NPD1511	Approved
0.7415	Intermediate Similarity	NPD3539	Phase 1
0.741	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4908	Phase 1
0.7394	Intermediate Similarity	NPD6832	Phase 2
0.7391	Intermediate Similarity	NPD1611	Approved
0.7386	Intermediate Similarity	NPD920	Approved
0.7375	Intermediate Similarity	NPD7199	Phase 2
0.7372	Intermediate Similarity	NPD1778	Approved
0.7365	Intermediate Similarity	NPD3540	Phase 1
0.7362	Intermediate Similarity	NPD3818	Discontinued
0.7357	Intermediate Similarity	NPD3225	Approved
0.7355	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1465	Phase 2
0.7325	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7819	Suspended
0.732	Intermediate Similarity	NPD1512	Approved
0.7317	Intermediate Similarity	NPD7054	Approved
0.7315	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD4357	Discontinued
0.7303	Intermediate Similarity	NPD5297	Approved
0.7299	Intermediate Similarity	NPD5585	Approved
0.7297	Intermediate Similarity	NPD1551	Phase 2
0.7297	Intermediate Similarity	NPD2935	Discontinued
0.7292	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5242	Approved
0.7284	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7472	Approved
0.7273	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD1243	Approved
0.7266	Intermediate Similarity	NPD1610	Phase 2
0.7266	Intermediate Similarity	NPD1091	Approved
0.7261	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD6801	Discontinued
0.726	Intermediate Similarity	NPD4340	Discontinued
0.7255	Intermediate Similarity	NPD5401	Approved
0.7255	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1019	Discontinued
0.7248	Intermediate Similarity	NPD7266	Discontinued
0.7246	Intermediate Similarity	NPD4626	Approved
0.7241	Intermediate Similarity	NPD6233	Phase 2
0.7239	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6166	Phase 2
0.7237	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4965	Approved
0.7233	Intermediate Similarity	NPD4967	Phase 2
0.7233	Intermediate Similarity	NPD4966	Approved
0.7226	Intermediate Similarity	NPD3687	Approved
0.7226	Intermediate Similarity	NPD3686	Approved
0.7222	Intermediate Similarity	NPD6232	Discontinued
0.7211	Intermediate Similarity	NPD2653	Approved
0.7203	Intermediate Similarity	NPD2237	Approved
0.7203	Intermediate Similarity	NPD2861	Phase 2
0.7197	Intermediate Similarity	NPD6386	Approved
0.7197	Intermediate Similarity	NPD6385	Approved
0.719	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7075	Discontinued
0.7183	Intermediate Similarity	NPD3267	Approved
0.7183	Intermediate Similarity	NPD2797	Approved
0.7183	Intermediate Similarity	NPD3266	Approved
0.7178	Intermediate Similarity	NPD3926	Phase 2
0.7171	Intermediate Similarity	NPD6190	Approved
0.7169	Intermediate Similarity	NPD7074	Phase 3
0.7163	Intermediate Similarity	NPD4749	Approved
0.716	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3146	Approved
0.7143	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7134	Intermediate Similarity	NPD4678	Approved
0.7134	Intermediate Similarity	NPD4675	Approved
0.7132	Intermediate Similarity	NPD6671	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6797	Phase 2
0.7121	Intermediate Similarity	NPD2684	Approved
0.7111	Intermediate Similarity	NPD1241	Discontinued
0.7105	Intermediate Similarity	NPD4110	Phase 3
0.7105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4628	Phase 3
0.7105	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD9717	Approved
0.7091	Intermediate Similarity	NPD7473	Discontinued
0.709	Intermediate Similarity	NPD228	Approved
0.7089	Intermediate Similarity	NPD5090	Approved
0.7089	Intermediate Similarity	NPD5089	Approved
0.7089	Intermediate Similarity	NPD7411	Suspended
0.7083	Intermediate Similarity	NPD7251	Discontinued
0.7081	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4307	Phase 2
0.707	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2219	Phase 1
0.7055	Intermediate Similarity	NPD3268	Approved
0.7055	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7045	Intermediate Similarity	NPD290	Approved
0.7042	Intermediate Similarity	NPD4359	Approved
0.7039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7843	Approved
0.7034	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7025	Intermediate Similarity	NPD4380	Phase 2
0.702	Intermediate Similarity	NPD1375	Discontinued
0.702	Intermediate Similarity	NPD5762	Approved
0.702	Intermediate Similarity	NPD5763	Approved
0.7019	Intermediate Similarity	NPD7768	Phase 2
0.7007	Intermediate Similarity	NPD7157	Approved
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD4585	Approved
0.6993	Remote Similarity	NPD8651	Approved
0.6987	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7095	Approved
0.6986	Remote Similarity	NPD4625	Phase 3
0.6974	Remote Similarity	NPD2424	Discontinued
0.6974	Remote Similarity	NPD1549	Phase 2
0.6968	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6032	Approved
0.6944	Remote Similarity	NPD1203	Approved
0.6939	Remote Similarity	NPD411	Approved
0.6933	Remote Similarity	NPD6111	Discontinued
0.6929	Remote Similarity	NPD1357	Approved
0.6928	Remote Similarity	NPD6674	Discontinued
0.6923	Remote Similarity	NPD2534	Approved
0.6923	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD2532	Approved
0.6908	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7644	Approved
0.6906	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7124	Phase 2
0.6897	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7033	Discontinued
0.6887	Remote Similarity	NPD4308	Phase 3
0.6882	Remote Similarity	NPD6559	Discontinued
0.6875	Remote Similarity	NPD2922	Phase 1
0.6875	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7975	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