NPASS Compound

Structure

NPC89408 OpenBabel07101719152D 28 30 0 0 1 0 0 0 0 0999 V2000 6.9282 -4.0000 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 3.0981 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.3660 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 4.3301 -0.5000 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 -0.0000 -2.0000 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 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 2.5981 -0.5000 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 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -2.5981 -1.5000 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 3.4641 2.0000 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 14 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 13 16 1 0 0 0 0 13 26 1 0 0 0 0 14 20 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 17 16 1 6 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 22 1 0 0 0 0 18 23 2 0 0 0 0 19 22 1 1 0 0 0 19 28 1 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 12 1 1 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.2
Volume:	402.958
LogP:	3.872
LogD:	2.427
LogS:	-3.725
# Rotatable Bonds:	8
TPSA:	85.36
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	4.92
Fsp3:	0.636
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:	-5.025
MDCK Permeability:	2.587525887065567e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.084
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.837
Plasma Protein Binding (PPB):	93.78276062011719%
Volume Distribution (VD):	1.644
Pgp-substrate:	4.51911735534668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.778
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	1.094
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.235
Rat Oral Acute Toxicity:	0.32
Maximum Recommended Daily Dose:	0.461
Skin Sensitization:	0.522
Carcinogencity:	0.708
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC89408

Natural Product ID:	NPC89408
*Common Name:**	(E)-4-[(1Ar,7Ar,7Br)-3-[(E)-Hept-1-Enyl]-6,6-Dimethyl-2-Oxo-7A,7B-Dihydro-4H-Oxireno[2,3-H][1,3]Benzodioxin-1A-Yl]-2-Methylbut-2-Enoic Acid
IUPAC Name:	(E)-4-[(1aR,7aR,7bR)-3-[(E)-hept-1-enyl]-6,6-dimethyl-2-oxo-7a,7b-dihydro-4H-oxireno[2,3-h][1,3]benzodioxin-1a-yl]-2-methylbut-2-enoic acid
Synonyms:
Standard InCHIKey:	KJESBKJFNPXHOA-LNZGVCCXSA-N
Standard InCHI:	InChI=1S/C22H30O6/c1-5-6-7-8-9-10-15-16-13-26-21(3,4)27-17(16)19-22(28-19,18(15)23)12-11-14(2)20(24)25/h9-11,17,19H,5-8,12-13H2,1-4H3,(H,24,25)/b10-9+,14-11+/t17-,19-,22+/m1/s1
SMILES:	CCCCC/C=C/C1=C2COC(C)(C)O[C@H]2[C@@H]2[C@](C/C=C(C)/C(=O)O)(C1=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558344
PubChem CID:	25207983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0001989] Heterocyclic fatty acids

*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
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19117486]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	chinese mangrove plant Rhizophora mucronata	n.a.	n.a.	PMID[19271764]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	Chinese mangrove plant Rhizophoramucronata	n.a.	n.a.	PMID[19762244]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	Isolated from the branches of Podocarpus macrophyllus	Kunming World Horticultural Exposition Garden, Kunming, China	2002-NOV	PMID[21302965]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24168147]

☑ 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	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	50000.0	nM	PMID[459744]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	>	50000.0	nM	PMID[459744]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	50000.0	nM	PMID[459744]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50000.0	nM	PMID[459744]
NPT3594	Organism	Galactomyces geotrichum	Galactomyces geotrichum	IC50	>	50000.0	nM	PMID[459744]

☑ 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 NPC89408 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	220
0.1-0.2	1260
0.2-0.3	4088
0.3-0.4	7668
0.4-0.5	14966
0.5-0.6	9763
0.6-0.7	4002
0.7-0.8	709
0.8-0.85	15
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.932	High Similarity	NPC266514
0.9029	High Similarity	NPC104161
0.9029	High Similarity	NPC118902
0.9029	High Similarity	NPC469980
0.8571	High Similarity	NPC39996
0.8349	Intermediate Similarity	NPC264819
0.8182	Intermediate Similarity	NPC327106
0.8125	Intermediate Similarity	NPC317107
0.8091	Intermediate Similarity	NPC469853
0.8058	Intermediate Similarity	NPC142838
0.8053	Intermediate Similarity	NPC317687
0.8018	Intermediate Similarity	NPC322903
0.8	Intermediate Similarity	NPC270478
0.784	Intermediate Similarity	NPC471137
0.784	Intermediate Similarity	NPC223356
0.784	Intermediate Similarity	NPC475154
0.784	Intermediate Similarity	NPC473548
0.784	Intermediate Similarity	NPC475500
0.784	Intermediate Similarity	NPC471136
0.784	Intermediate Similarity	NPC100017
0.784	Intermediate Similarity	NPC182266
0.7807	Intermediate Similarity	NPC304180
0.7807	Intermediate Similarity	NPC179798
0.7798	Intermediate Similarity	NPC164598
0.7798	Intermediate Similarity	NPC474339
0.7778	Intermediate Similarity	NPC23046
0.7769	Intermediate Similarity	NPC470922
0.7768	Intermediate Similarity	NPC474716
0.7742	Intermediate Similarity	NPC251564
0.7742	Intermediate Similarity	NPC475314
0.7742	Intermediate Similarity	NPC475606
0.7742	Intermediate Similarity	NPC476862
0.7742	Intermediate Similarity	NPC476863
0.7742	Intermediate Similarity	NPC477189
0.7724	Intermediate Similarity	NPC476859
0.7717	Intermediate Similarity	NPC68282
0.7712	Intermediate Similarity	NPC474286
0.7712	Intermediate Similarity	NPC475130
0.7706	Intermediate Similarity	NPC469551
0.7706	Intermediate Similarity	NPC324667
0.7692	Intermediate Similarity	NPC477509
0.7685	Intermediate Similarity	NPC266842
0.768	Intermediate Similarity	NPC474508
0.768	Intermediate Similarity	NPC231240
0.768	Intermediate Similarity	NPC473485
0.768	Intermediate Similarity	NPC180902
0.768	Intermediate Similarity	NPC475139
0.7679	Intermediate Similarity	NPC469852
0.7679	Intermediate Similarity	NPC477125
0.7672	Intermediate Similarity	NPC469496
0.7672	Intermediate Similarity	NPC159333
0.7672	Intermediate Similarity	NPC56448
0.7672	Intermediate Similarity	NPC469454
0.7672	Intermediate Similarity	NPC469463
0.7667	Intermediate Similarity	NPC67569
0.7664	Intermediate Similarity	NPC227494
0.7661	Intermediate Similarity	NPC473593
0.7642	Intermediate Similarity	NPC287423
0.7642	Intermediate Similarity	NPC471940
0.7636	Intermediate Similarity	NPC469851
0.7636	Intermediate Similarity	NPC112613
0.7636	Intermediate Similarity	NPC207885
0.7632	Intermediate Similarity	NPC87335
0.7627	Intermediate Similarity	NPC469684
0.7619	Intermediate Similarity	NPC316915
0.7615	Intermediate Similarity	NPC264378
0.7615	Intermediate Similarity	NPC161855
0.7603	Intermediate Similarity	NPC23786
0.7603	Intermediate Similarity	NPC470265
0.76	Intermediate Similarity	NPC476852
0.76	Intermediate Similarity	NPC476855
0.7593	Intermediate Similarity	NPC473291
0.7589	Intermediate Similarity	NPC146731
0.7589	Intermediate Similarity	NPC474741
0.7583	Intermediate Similarity	NPC48692
0.7565	Intermediate Similarity	NPC5103
0.7565	Intermediate Similarity	NPC235014
0.7563	Intermediate Similarity	NPC284707
0.7561	Intermediate Similarity	NPC225049
0.7561	Intermediate Similarity	NPC471939
0.7547	Intermediate Similarity	NPC32552
0.7545	Intermediate Similarity	NPC475053
0.7544	Intermediate Similarity	NPC102843
0.7544	Intermediate Similarity	NPC472507
0.7541	Intermediate Similarity	NPC120724
0.7541	Intermediate Similarity	NPC469789
0.754	Intermediate Similarity	NPC476193
0.7522	Intermediate Similarity	NPC472645
0.7522	Intermediate Similarity	NPC475802
0.7521	Intermediate Similarity	NPC477126
0.752	Intermediate Similarity	NPC476851
0.752	Intermediate Similarity	NPC476854
0.752	Intermediate Similarity	NPC162495
0.75	Intermediate Similarity	NPC473334
0.75	Intermediate Similarity	NPC268958
0.748	Intermediate Similarity	NPC168879
0.748	Intermediate Similarity	NPC32868
0.748	Intermediate Similarity	NPC473919
0.748	Intermediate Similarity	NPC241456
0.748	Intermediate Similarity	NPC473709
0.748	Intermediate Similarity	NPC24651
0.7479	Intermediate Similarity	NPC27999
0.7479	Intermediate Similarity	NPC477116
0.7479	Intermediate Similarity	NPC53396
0.7479	Intermediate Similarity	NPC98249
0.7477	Intermediate Similarity	NPC201718
0.7458	Intermediate Similarity	NPC305044
0.7458	Intermediate Similarity	NPC265290
0.7456	Intermediate Similarity	NPC469558
0.7455	Intermediate Similarity	NPC307517
0.7455	Intermediate Similarity	NPC255592
0.7455	Intermediate Similarity	NPC203627
0.7455	Intermediate Similarity	NPC81483
0.7455	Intermediate Similarity	NPC261377
0.7455	Intermediate Similarity	NPC61630
0.7455	Intermediate Similarity	NPC187761
0.7455	Intermediate Similarity	NPC308567
0.7455	Intermediate Similarity	NPC83895
0.7455	Intermediate Similarity	NPC169468
0.7453	Intermediate Similarity	NPC477684
0.7442	Intermediate Similarity	NPC243014
0.744	Intermediate Similarity	NPC473620
0.744	Intermediate Similarity	NPC236999
0.7438	Intermediate Similarity	NPC476815
0.7438	Intermediate Similarity	NPC473145
0.7438	Intermediate Similarity	NPC107338
0.7438	Intermediate Similarity	NPC109607
0.7436	Intermediate Similarity	NPC269530
0.7434	Intermediate Similarity	NPC471937
0.7434	Intermediate Similarity	NPC296950
0.7434	Intermediate Similarity	NPC471143
0.7434	Intermediate Similarity	NPC477510
0.7431	Intermediate Similarity	NPC288350
0.7431	Intermediate Similarity	NPC173329
0.7431	Intermediate Similarity	NPC279722
0.7422	Intermediate Similarity	NPC471234
0.7419	Intermediate Similarity	NPC293112
0.7419	Intermediate Similarity	NPC222307
0.7419	Intermediate Similarity	NPC217901
0.7417	Intermediate Similarity	NPC251310
0.7417	Intermediate Similarity	NPC50774
0.7417	Intermediate Similarity	NPC240509
0.7417	Intermediate Similarity	NPC186525
0.7417	Intermediate Similarity	NPC709
0.7417	Intermediate Similarity	NPC234522
0.7414	Intermediate Similarity	NPC115257
0.7414	Intermediate Similarity	NPC281624
0.7414	Intermediate Similarity	NPC161816
0.7414	Intermediate Similarity	NPC472508
0.7411	Intermediate Similarity	NPC471148
0.7411	Intermediate Similarity	NPC473596
0.7411	Intermediate Similarity	NPC149371
0.7407	Intermediate Similarity	NPC471496
0.7404	Intermediate Similarity	NPC196381
0.7398	Intermediate Similarity	NPC204812
0.7398	Intermediate Similarity	NPC67251
0.7398	Intermediate Similarity	NPC473802
0.7391	Intermediate Similarity	NPC151393
0.7391	Intermediate Similarity	NPC233379
0.7391	Intermediate Similarity	NPC14862
0.7391	Intermediate Similarity	NPC474664
0.7387	Intermediate Similarity	NPC288876
0.7383	Intermediate Similarity	NPC470373
0.7383	Intermediate Similarity	NPC470379
0.7381	Intermediate Similarity	NPC477076
0.7381	Intermediate Similarity	NPC476966
0.7381	Intermediate Similarity	NPC477079
0.7381	Intermediate Similarity	NPC477077
0.7381	Intermediate Similarity	NPC470913
0.7381	Intermediate Similarity	NPC471407
0.7379	Intermediate Similarity	NPC469809
0.7377	Intermediate Similarity	NPC477046
0.7377	Intermediate Similarity	NPC102822
0.7377	Intermediate Similarity	NPC183353
0.7377	Intermediate Similarity	NPC469812
0.7377	Intermediate Similarity	NPC170880
0.7377	Intermediate Similarity	NPC469515
0.7373	Intermediate Similarity	NPC471204
0.7373	Intermediate Similarity	NPC264153
0.7373	Intermediate Similarity	NPC321496
0.7373	Intermediate Similarity	NPC101965
0.7373	Intermediate Similarity	NPC101400
0.7368	Intermediate Similarity	NPC472751
0.7368	Intermediate Similarity	NPC1679
0.7368	Intermediate Similarity	NPC472749
0.7368	Intermediate Similarity	NPC16313
0.7368	Intermediate Similarity	NPC9303
0.7368	Intermediate Similarity	NPC252296
0.7364	Intermediate Similarity	NPC474194
0.7364	Intermediate Similarity	NPC40812
0.736	Intermediate Similarity	NPC168849
0.736	Intermediate Similarity	NPC473253
0.736	Intermediate Similarity	NPC475273
0.736	Intermediate Similarity	NPC42399
0.7355	Intermediate Similarity	NPC236918
0.7355	Intermediate Similarity	NPC156745
0.7355	Intermediate Similarity	NPC475775
0.7355	Intermediate Similarity	NPC476529
0.7355	Intermediate Similarity	NPC245320
0.7355	Intermediate Similarity	NPC476107

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 NPC89408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1466
0.2-0.3	3494
0.3-0.4	2591
0.4-0.5	964
0.5-0.6	367
0.6-0.7	74
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7615	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8515	Approved
0.7377	Intermediate Similarity	NPD8513	Phase 3
0.7377	Intermediate Similarity	NPD8516	Approved
0.7377	Intermediate Similarity	NPD8517	Approved
0.7333	Intermediate Similarity	NPD7115	Discovery
0.7232	Intermediate Similarity	NPD6648	Approved
0.713	Intermediate Similarity	NPD6698	Approved
0.713	Intermediate Similarity	NPD46	Approved
0.713	Intermediate Similarity	NPD7838	Discovery
0.7087	Intermediate Similarity	NPD8074	Phase 3
0.7063	Intermediate Similarity	NPD7492	Approved
0.7059	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5344	Discontinued
0.7016	Intermediate Similarity	NPD6054	Approved
0.7008	Intermediate Similarity	NPD6616	Approved
0.6991	Remote Similarity	NPD4225	Approved
0.6984	Remote Similarity	NPD8328	Phase 3
0.696	Remote Similarity	NPD6016	Approved
0.696	Remote Similarity	NPD6015	Approved
0.6953	Remote Similarity	NPD7078	Approved
0.6911	Remote Similarity	NPD6009	Approved
0.6905	Remote Similarity	NPD6370	Approved
0.6905	Remote Similarity	NPD5988	Approved
0.6899	Remote Similarity	NPD7736	Approved
0.688	Remote Similarity	NPD6319	Approved
0.6864	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5779	Approved
0.6847	Remote Similarity	NPD5778	Approved
0.6833	Remote Similarity	NPD6371	Approved
0.6833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6686	Approved
0.6807	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7983	Approved
0.675	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6059	Approved
0.6721	Remote Similarity	NPD6882	Approved
0.6719	Remote Similarity	NPD7830	Approved
0.6719	Remote Similarity	NPD7829	Approved
0.6693	Remote Similarity	NPD7503	Approved
0.6692	Remote Similarity	NPD8293	Discontinued
0.664	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5282	Discontinued
0.6618	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7260	Phase 2
0.6591	Remote Similarity	NPD7319	Approved
0.6589	Remote Similarity	NPD7642	Approved
0.6585	Remote Similarity	NPD8297	Approved
0.6583	Remote Similarity	NPD5697	Approved
0.6583	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4756	Discovery
0.6532	Remote Similarity	NPD4632	Approved
0.6529	Remote Similarity	NPD6899	Approved
0.6529	Remote Similarity	NPD6881	Approved
0.6522	Remote Similarity	NPD7839	Suspended
0.6504	Remote Similarity	NPD6649	Approved
0.6504	Remote Similarity	NPD6650	Approved
0.6496	Remote Similarity	NPD7639	Approved
0.6496	Remote Similarity	NPD7640	Approved
0.6489	Remote Similarity	NPD7507	Approved
0.6475	Remote Similarity	NPD6013	Approved
0.6475	Remote Similarity	NPD6014	Approved
0.6475	Remote Similarity	NPD6012	Approved
0.6462	Remote Similarity	NPD7604	Phase 2
0.6434	Remote Similarity	NPD5983	Phase 2
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6423	Remote Similarity	NPD7290	Approved
0.6423	Remote Similarity	NPD7102	Approved
0.6423	Remote Similarity	NPD6883	Approved
0.641	Remote Similarity	NPD7638	Approved
0.6393	Remote Similarity	NPD6011	Approved
0.6378	Remote Similarity	NPD7500	Approved
0.6371	Remote Similarity	NPD6869	Approved
0.6371	Remote Similarity	NPD6847	Approved
0.6371	Remote Similarity	NPD6617	Approved
0.6371	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD1694	Approved
0.6364	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD6675	Approved
0.6364	Remote Similarity	NPD5739	Approved
0.6364	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7128	Approved
0.6364	Remote Similarity	NPD6402	Approved
0.6364	Remote Similarity	NPD8451	Approved
0.6341	Remote Similarity	NPD6372	Approved
0.6341	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6373	Approved
0.6328	Remote Similarity	NPD7327	Approved
0.6328	Remote Similarity	NPD7328	Approved
0.6316	Remote Similarity	NPD8448	Approved
0.6316	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD6412	Phase 2
0.6311	Remote Similarity	NPD5701	Approved
0.6308	Remote Similarity	NPD8033	Approved
0.6293	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4634	Approved
0.6288	Remote Similarity	NPD8341	Approved
0.6288	Remote Similarity	NPD8340	Approved
0.6288	Remote Similarity	NPD8299	Approved
0.6288	Remote Similarity	NPD8342	Approved
0.6279	Remote Similarity	NPD7516	Approved
0.6269	Remote Similarity	NPD6033	Approved
0.626	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.6241	Remote Similarity	NPD8273	Phase 1
0.6241	Remote Similarity	NPD6336	Discontinued
0.6239	Remote Similarity	NPD5209	Approved
0.6231	Remote Similarity	NPD8294	Approved
0.6231	Remote Similarity	NPD8377	Approved
0.6228	Remote Similarity	NPD5785	Approved
0.6216	Remote Similarity	NPD1696	Phase 3
0.6204	Remote Similarity	NPD6845	Suspended
0.6202	Remote Similarity	NPD7641	Discontinued
0.619	Remote Similarity	NPD6053	Discontinued
0.6186	Remote Similarity	NPD7902	Approved
0.6183	Remote Similarity	NPD8444	Approved
0.6183	Remote Similarity	NPD6921	Approved
0.6183	Remote Similarity	NPD8296	Approved
0.6183	Remote Similarity	NPD8335	Approved
0.6183	Remote Similarity	NPD8380	Approved
0.6183	Remote Similarity	NPD8379	Approved
0.6183	Remote Similarity	NPD8378	Approved
0.6182	Remote Similarity	NPD6110	Phase 1
0.6176	Remote Similarity	NPD8391	Approved
0.6176	Remote Similarity	NPD8390	Approved
0.6176	Remote Similarity	NPD8392	Approved
0.6176	Remote Similarity	NPD5956	Approved
0.6154	Remote Similarity	NPD5695	Phase 3
0.6148	Remote Similarity	NPD5141	Approved
0.614	Remote Similarity	NPD1695	Approved
0.6134	Remote Similarity	NPD5696	Approved
0.6083	Remote Similarity	NPD4696	Approved
0.6083	Remote Similarity	NPD5285	Approved
0.6083	Remote Similarity	NPD5286	Approved
0.6071	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5363	Approved
0.6068	Remote Similarity	NPD7748	Approved
0.6055	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6084	Phase 2
0.605	Remote Similarity	NPD6083	Phase 2
0.6047	Remote Similarity	NPD6274	Approved
0.6034	Remote Similarity	NPD7637	Suspended
0.6031	Remote Similarity	NPD7100	Approved
0.6031	Remote Similarity	NPD7101	Approved
0.6016	Remote Similarity	NPD8133	Approved
0.6015	Remote Similarity	NPD8080	Discontinued
0.6	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD6317	Approved
0.5984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD4633	Approved
0.5984	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD7632	Discontinued
0.5984	Remote Similarity	NPD5225	Approved
0.5984	Remote Similarity	NPD5226	Approved
0.5983	Remote Similarity	NPD6399	Phase 3
0.5982	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD3573	Approved
0.5954	Remote Similarity	NPD6313	Approved
0.5954	Remote Similarity	NPD6335	Approved
0.5954	Remote Similarity	NPD6314	Approved
0.5935	Remote Similarity	NPD5174	Approved
0.5935	Remote Similarity	NPD5175	Approved
0.5932	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7900	Approved
0.5926	Remote Similarity	NPD7799	Discontinued
0.5917	Remote Similarity	NPD4755	Approved
0.5902	Remote Similarity	NPD5223	Approved
0.5897	Remote Similarity	NPD7515	Phase 2
0.5897	Remote Similarity	NPD5693	Phase 1
0.5897	Remote Similarity	NPD5694	Approved
0.5897	Remote Similarity	NPD5284	Approved
0.5897	Remote Similarity	NPD5281	Approved
0.5879	Remote Similarity	NPD8368	Discontinued
0.5877	Remote Similarity	NPD4249	Approved
0.5859	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5222	Approved
0.5833	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5221	Approved
0.5828	Remote Similarity	NPD3751	Discontinued
0.5826	Remote Similarity	NPD4250	Approved
0.5826	Remote Similarity	NPD4251	Approved
0.5821	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.582	Remote Similarity	NPD4700	Approved
0.5812	Remote Similarity	NPD5692	Phase 3
0.5812	Remote Similarity	NPD3168	Discontinued
0.5804	Remote Similarity	NPD4269	Approved
0.5804	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD4270	Approved
0.5802	Remote Similarity	NPD6868	Approved
0.5785	Remote Similarity	NPD5173	Approved
0.5784	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD2067	Discontinued
0.5776	Remote Similarity	NPD5737	Approved
0.5776	Remote Similarity	NPD6672	Approved
0.5774	Remote Similarity	NPD8407	Phase 2
0.5766	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4252	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