NPASS Compound

Structure

NPC142838 OpenBabel07101719242D 25 25 0 0 1 0 0 0 0 0999 V2000 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 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 -5.1962 -2.0000 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 -3.4641 -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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7321 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 -0.0000 -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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 13 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 16 21 2 0 0 0 0 17 19 1 6 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.19
Volume:	368.183
LogP:	2.487
LogD:	1.073
LogS:	-2.391
# Rotatable Bonds:	10
TPSA:	108.74
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.27
Synthetic Accessibility Score:	4.533
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.148
MDCK Permeability:	3.234190808143467e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.583
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.36
Plasma Protein Binding (PPB):	53.26947021484375%
Volume Distribution (VD):	0.502
Pgp-substrate:	41.99985122680664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.214
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.569
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	3.206
Half-life (T1/2):	0.503

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.436
Carcinogencity:	0.042
Eye Corrosion:	0.868
Eye Irritation:	0.118
Respiratory Toxicity:	0.782

Download Data

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

Natural Product: NPC142838

Natural Product ID:	NPC142838
*Common Name:**	4-((1R,2S)-3-(Hept-1-Enyl)-1,2-Dihydroxy-4-(Hydroxymethyl)-5-Oxocyclohex-3-Enyl)-2-Methylbut-2-Enoic Acid
IUPAC Name:	(E)-4-[(1R,2S)-3-[(E)-hept-1-enyl]-1,2-dihydroxy-4-(hydroxymethyl)-5-oxocyclohex-3-en-1-yl]-2-methylbut-2-enoic acid
Synonyms:
Standard InCHIKey:	URCJGSIEVALIMC-SJCXCURWSA-N
Standard InCHI:	InChI=1S/C19H28O6/c1-3-4-5-6-7-8-14-15(12-20)16(21)11-19(25,17(14)22)10-9-13(2)18(23)24/h7-9,17,20,22,25H,3-6,10-12H2,1-2H3,(H,23,24)/b8-7+,13-9+/t17-,19+/m0/s1
SMILES:	CCCCC/C=C/C1=C(CO)C(=O)C[C@]([C@H]1O)(O)C/C=C(/C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551172
PubChem CID:	25207984
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0000341] Hydroxy 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[509144]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	>	50000.0	nM	PMID[509144]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	50000.0	nM	PMID[509144]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50000.0	nM	PMID[509144]
NPT3594	Organism	Galactomyces geotrichum	Galactomyces geotrichum	IC50	>	50000.0	nM	PMID[509144]

☑ 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 NPC142838 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	191
0.1-0.2	1048
0.2-0.3	4451
0.3-0.4	8685
0.4-0.5	16183
0.5-0.6	7923
0.6-0.7	3630
0.7-0.8	567
0.8-0.85	12
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC118902
0.8947	High Similarity	NPC469980
0.8947	High Similarity	NPC104161
0.8673	High Similarity	NPC266514
0.8454	Intermediate Similarity	NPC39996
0.8427	Intermediate Similarity	NPC187529
0.8058	Intermediate Similarity	NPC89408
0.8039	Intermediate Similarity	NPC264819
0.8	Intermediate Similarity	NPC475050
0.7912	Intermediate Similarity	NPC302360
0.7895	Intermediate Similarity	NPC116726
0.7802	Intermediate Similarity	NPC477785
0.7802	Intermediate Similarity	NPC477784
0.7802	Intermediate Similarity	NPC477786
0.7802	Intermediate Similarity	NPC57370
0.78	Intermediate Similarity	NPC282524
0.7767	Intermediate Similarity	NPC469853
0.7767	Intermediate Similarity	NPC473284
0.7766	Intermediate Similarity	NPC229612
0.7766	Intermediate Similarity	NPC7280
0.7732	Intermediate Similarity	NPC196227
0.7727	Intermediate Similarity	NPC471061
0.7727	Intermediate Similarity	NPC97173
0.7692	Intermediate Similarity	NPC224455
0.7684	Intermediate Similarity	NPC118011
0.7684	Intermediate Similarity	NPC36668
0.7677	Intermediate Similarity	NPC99726
0.7653	Intermediate Similarity	NPC272050
0.7647	Intermediate Similarity	NPC95899
0.7634	Intermediate Similarity	NPC15807
0.76	Intermediate Similarity	NPC278008
0.76	Intermediate Similarity	NPC316598
0.7596	Intermediate Similarity	NPC330011
0.7596	Intermediate Similarity	NPC329048
0.7582	Intermediate Similarity	NPC474980
0.7576	Intermediate Similarity	NPC301534
0.7576	Intermediate Similarity	NPC250757
0.757	Intermediate Similarity	NPC476801
0.7551	Intermediate Similarity	NPC78159
0.7551	Intermediate Similarity	NPC181393
0.7551	Intermediate Similarity	NPC217624
0.7547	Intermediate Similarity	NPC286880
0.7528	Intermediate Similarity	NPC82666
0.7527	Intermediate Similarity	NPC219966
0.7526	Intermediate Similarity	NPC303230
0.7526	Intermediate Similarity	NPC6099
0.7526	Intermediate Similarity	NPC114345
0.7525	Intermediate Similarity	NPC198880
0.7524	Intermediate Similarity	NPC476802
0.7524	Intermediate Similarity	NPC89171
0.7524	Intermediate Similarity	NPC151393
0.7524	Intermediate Similarity	NPC102843
0.75	Intermediate Similarity	NPC206001
0.75	Intermediate Similarity	NPC314727
0.75	Intermediate Similarity	NPC469852
0.75	Intermediate Similarity	NPC474938
0.75	Intermediate Similarity	NPC20066
0.75	Intermediate Similarity	NPC218927
0.75	Intermediate Similarity	NPC474785
0.7477	Intermediate Similarity	NPC188738
0.7476	Intermediate Similarity	NPC72151
0.7476	Intermediate Similarity	NPC478057
0.7475	Intermediate Similarity	NPC476245
0.7475	Intermediate Similarity	NPC53565
0.7474	Intermediate Similarity	NPC472007
0.7453	Intermediate Similarity	NPC475065
0.7451	Intermediate Similarity	NPC97435
0.7451	Intermediate Similarity	NPC115862
0.7449	Intermediate Similarity	NPC476049
0.7449	Intermediate Similarity	NPC29798
0.7449	Intermediate Similarity	NPC282644
0.7447	Intermediate Similarity	NPC109528
0.7447	Intermediate Similarity	NPC11804
0.7447	Intermediate Similarity	NPC261380
0.7444	Intermediate Similarity	NPC478122
0.7431	Intermediate Similarity	NPC147912
0.7431	Intermediate Similarity	NPC67259
0.7429	Intermediate Similarity	NPC472925
0.7426	Intermediate Similarity	NPC300584
0.7426	Intermediate Similarity	NPC103051
0.7426	Intermediate Similarity	NPC478056
0.7423	Intermediate Similarity	NPC166554
0.7423	Intermediate Similarity	NPC473099
0.7423	Intermediate Similarity	NPC477684
0.7423	Intermediate Similarity	NPC265856
0.7419	Intermediate Similarity	NPC16488
0.7419	Intermediate Similarity	NPC251475
0.7419	Intermediate Similarity	NPC169941
0.7404	Intermediate Similarity	NPC146731
0.7404	Intermediate Similarity	NPC296950
0.74	Intermediate Similarity	NPC117133
0.74	Intermediate Similarity	NPC473291
0.7396	Intermediate Similarity	NPC477302
0.7396	Intermediate Similarity	NPC72397
0.7396	Intermediate Similarity	NPC48107
0.7396	Intermediate Similarity	NPC136879
0.7396	Intermediate Similarity	NPC473229
0.7391	Intermediate Similarity	NPC275766
0.7391	Intermediate Similarity	NPC470298
0.7386	Intermediate Similarity	NPC122244
0.7379	Intermediate Similarity	NPC293753
0.7379	Intermediate Similarity	NPC320447
0.7374	Intermediate Similarity	NPC470957
0.7374	Intermediate Similarity	NPC279410
0.7374	Intermediate Similarity	NPC470958
0.7374	Intermediate Similarity	NPC299100
0.7374	Intermediate Similarity	NPC472976
0.7374	Intermediate Similarity	NPC119562
0.7374	Intermediate Similarity	NPC472977
0.7368	Intermediate Similarity	NPC315395
0.7368	Intermediate Similarity	NPC316426
0.7368	Intermediate Similarity	NPC473226
0.7368	Intermediate Similarity	NPC472009
0.7368	Intermediate Similarity	NPC196381
0.7368	Intermediate Similarity	NPC164393
0.7364	Intermediate Similarity	NPC64318
0.7363	Intermediate Similarity	NPC246458
0.7358	Intermediate Similarity	NPC473482
0.7358	Intermediate Similarity	NPC475418
0.7358	Intermediate Similarity	NPC318363
0.7353	Intermediate Similarity	NPC475053
0.7353	Intermediate Similarity	NPC266955
0.7353	Intermediate Similarity	NPC306856
0.7347	Intermediate Similarity	NPC32552
0.7347	Intermediate Similarity	NPC327760
0.7347	Intermediate Similarity	NPC73457
0.7345	Intermediate Similarity	NPC67569
0.734	Intermediate Similarity	NPC472326
0.7339	Intermediate Similarity	NPC469463
0.7339	Intermediate Similarity	NPC469454
0.7339	Intermediate Similarity	NPC469496
0.7333	Intermediate Similarity	NPC166607
0.7333	Intermediate Similarity	NPC47844
0.7333	Intermediate Similarity	NPC477125
0.7333	Intermediate Similarity	NPC323834
0.7333	Intermediate Similarity	NPC141195
0.7327	Intermediate Similarity	NPC320306
0.7327	Intermediate Similarity	NPC470522
0.7327	Intermediate Similarity	NPC287668
0.7327	Intermediate Similarity	NPC108078
0.7327	Intermediate Similarity	NPC471694
0.7327	Intermediate Similarity	NPC135685
0.7327	Intermediate Similarity	NPC40812
0.7326	Intermediate Similarity	NPC143396
0.732	Intermediate Similarity	NPC212598
0.732	Intermediate Similarity	NPC473100
0.7315	Intermediate Similarity	NPC474315
0.7315	Intermediate Similarity	NPC304180
0.7315	Intermediate Similarity	NPC472928
0.7315	Intermediate Similarity	NPC317107
0.7315	Intermediate Similarity	NPC179798
0.7315	Intermediate Similarity	NPC324683
0.7312	Intermediate Similarity	NPC158411
0.7312	Intermediate Similarity	NPC38796
0.7308	Intermediate Similarity	NPC320294
0.7308	Intermediate Similarity	NPC99266
0.7308	Intermediate Similarity	NPC159533
0.7303	Intermediate Similarity	NPC166018
0.7303	Intermediate Similarity	NPC169056
0.7303	Intermediate Similarity	NPC225665
0.73	Intermediate Similarity	NPC88310
0.73	Intermediate Similarity	NPC180950
0.7297	Intermediate Similarity	NPC286528
0.7297	Intermediate Similarity	NPC167606
0.7297	Intermediate Similarity	NPC312824
0.7297	Intermediate Similarity	NPC20302
0.7297	Intermediate Similarity	NPC470492
0.7297	Intermediate Similarity	NPC470493
0.7297	Intermediate Similarity	NPC183580
0.7297	Intermediate Similarity	NPC140055
0.7292	Intermediate Similarity	NPC86005
0.7292	Intermediate Similarity	NPC181327
0.7292	Intermediate Similarity	NPC23622
0.729	Intermediate Similarity	NPC87335
0.7283	Intermediate Similarity	NPC470947
0.7283	Intermediate Similarity	NPC271104
0.7283	Intermediate Similarity	NPC160582
0.7283	Intermediate Similarity	NPC470945
0.7283	Intermediate Similarity	NPC470946
0.7282	Intermediate Similarity	NPC115899
0.7282	Intermediate Similarity	NPC469657
0.7282	Intermediate Similarity	NPC472924
0.7282	Intermediate Similarity	NPC469851
0.7282	Intermediate Similarity	NPC470184
0.7282	Intermediate Similarity	NPC308824
0.7282	Intermediate Similarity	NPC244456
0.7281	Intermediate Similarity	NPC470265
0.7281	Intermediate Similarity	NPC23786
0.7273	Intermediate Similarity	NPC215745
0.7273	Intermediate Similarity	NPC238948
0.7273	Intermediate Similarity	NPC469692
0.7273	Intermediate Similarity	NPC469645
0.7273	Intermediate Similarity	NPC12815
0.7264	Intermediate Similarity	NPC67321
0.7264	Intermediate Similarity	NPC187435
0.7263	Intermediate Similarity	NPC137033
0.7263	Intermediate Similarity	NPC79573
0.7257	Intermediate Similarity	NPC475885
0.7257	Intermediate Similarity	NPC476962
0.7255	Intermediate Similarity	NPC124512

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 NPC142838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1520
0.2-0.3	3624
0.3-0.4	2438
0.4-0.5	984
0.5-0.6	337
0.6-0.7	63
0.7-0.8	11
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
0.7449	Intermediate Similarity	NPD5778	Approved
0.7449	Intermediate Similarity	NPD5779	Approved
0.7297	Intermediate Similarity	NPD7115	Discovery
0.7263	Intermediate Similarity	NPD5363	Approved
0.7255	Intermediate Similarity	NPD4225	Approved
0.7172	Intermediate Similarity	NPD7983	Approved
0.6957	Remote Similarity	NPD4756	Discovery
0.6947	Remote Similarity	NPD4269	Approved
0.6947	Remote Similarity	NPD4270	Approved
0.6923	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4252	Approved
0.6907	Remote Similarity	NPD1696	Phase 3
0.69	Remote Similarity	NPD5785	Approved
0.69	Remote Similarity	NPD7838	Discovery
0.6832	Remote Similarity	NPD7515	Phase 2
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6101	Approved
0.6792	Remote Similarity	NPD5344	Discontinued
0.6757	Remote Similarity	NPD4634	Approved
0.6757	Remote Similarity	NPD6371	Approved
0.6752	Remote Similarity	NPD8515	Approved
0.6752	Remote Similarity	NPD8516	Approved
0.6752	Remote Similarity	NPD8517	Approved
0.6752	Remote Similarity	NPD8513	Phase 3
0.6737	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6698	Approved
0.6733	Remote Similarity	NPD46	Approved
0.6731	Remote Similarity	NPD7839	Suspended
0.6726	Remote Similarity	NPD4632	Approved
0.6705	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7640	Approved
0.6698	Remote Similarity	NPD7639	Approved
0.6698	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6604	Remote Similarity	NPD7638	Approved
0.6574	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD1694	Approved
0.6538	Remote Similarity	NPD7748	Approved
0.6531	Remote Similarity	NPD6110	Phase 1
0.6509	Remote Similarity	NPD7902	Approved
0.6505	Remote Similarity	NPD7637	Suspended
0.6505	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5284	Approved
0.6505	Remote Similarity	NPD6079	Approved
0.6505	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5697	Approved
0.6476	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8074	Phase 3
0.6471	Remote Similarity	NPD5370	Suspended
0.6455	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD5209	Approved
0.6429	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD5222	Approved
0.6415	Remote Similarity	NPD5221	Approved
0.6415	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6009	Approved
0.6404	Remote Similarity	NPD6650	Approved
0.6404	Remote Similarity	NPD6649	Approved
0.6395	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4819	Approved
0.6392	Remote Similarity	NPD4822	Approved
0.6392	Remote Similarity	NPD4820	Approved
0.6392	Remote Similarity	NPD4821	Approved
0.6389	Remote Similarity	NPD5286	Approved
0.6389	Remote Similarity	NPD4696	Approved
0.6389	Remote Similarity	NPD5285	Approved
0.6381	Remote Similarity	NPD5282	Discontinued
0.6372	Remote Similarity	NPD6014	Approved
0.6372	Remote Similarity	NPD6012	Approved
0.6372	Remote Similarity	NPD6013	Approved
0.6372	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD5362	Discontinued
0.6355	Remote Similarity	NPD5173	Approved
0.6354	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4268	Approved
0.6354	Remote Similarity	NPD4271	Approved
0.6348	Remote Similarity	NPD8297	Approved
0.633	Remote Similarity	NPD5223	Approved
0.6316	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD7290	Approved
0.6316	Remote Similarity	NPD6883	Approved
0.6311	Remote Similarity	NPD5328	Approved
0.6311	Remote Similarity	NPD7492	Approved
0.6286	Remote Similarity	NPD6399	Phase 3
0.6286	Remote Similarity	NPD4202	Approved
0.6283	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD3573	Approved
0.6273	Remote Similarity	NPD5225	Approved
0.6273	Remote Similarity	NPD4633	Approved
0.6273	Remote Similarity	NPD5224	Approved
0.6273	Remote Similarity	NPD5226	Approved
0.6263	Remote Similarity	NPD3667	Approved
0.6262	Remote Similarity	NPD4697	Phase 3
0.6261	Remote Similarity	NPD6847	Approved
0.6261	Remote Similarity	NPD6869	Approved
0.6261	Remote Similarity	NPD8130	Phase 1
0.6261	Remote Similarity	NPD6617	Approved
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6402	Approved
0.625	Remote Similarity	NPD6008	Approved
0.625	Remote Similarity	NPD6675	Approved
0.625	Remote Similarity	NPD5739	Approved
0.625	Remote Similarity	NPD7128	Approved
0.625	Remote Similarity	NPD6054	Approved
0.623	Remote Similarity	NPD8328	Phase 3
0.6228	Remote Similarity	NPD6372	Approved
0.6228	Remote Similarity	NPD6373	Approved
0.6226	Remote Similarity	NPD7900	Approved
0.6226	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7331	Phase 2
0.6216	Remote Similarity	NPD5175	Approved
0.6216	Remote Similarity	NPD5174	Approved
0.6211	Remote Similarity	NPD8264	Approved
0.621	Remote Similarity	NPD7078	Approved
0.6207	Remote Similarity	NPD6882	Approved
0.6204	Remote Similarity	NPD4755	Approved
0.62	Remote Similarity	NPD5331	Approved
0.62	Remote Similarity	NPD5332	Approved
0.6198	Remote Similarity	NPD6015	Approved
0.6198	Remote Similarity	NPD6016	Approved
0.6198	Remote Similarity	NPD5983	Phase 2
0.6195	Remote Similarity	NPD5701	Approved
0.618	Remote Similarity	NPD3197	Phase 1
0.6176	Remote Similarity	NPD4249	Approved
0.6176	Remote Similarity	NPD4519	Discontinued
0.6176	Remote Similarity	NPD4623	Approved
0.6176	Remote Similarity	NPD5279	Phase 3
0.6174	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4629	Approved
0.6168	Remote Similarity	NPD5210	Approved
0.6162	Remote Similarity	NPD4790	Discontinued
0.616	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5988	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.614	Remote Similarity	NPD6686	Approved
0.614	Remote Similarity	NPD7320	Approved
0.6139	Remote Similarity	NPD4786	Approved
0.6139	Remote Similarity	NPD3665	Phase 1
0.6139	Remote Similarity	NPD3666	Approved
0.6139	Remote Similarity	NPD3133	Approved
0.6134	Remote Similarity	NPD7500	Approved
0.6126	Remote Similarity	NPD7632	Discontinued
0.6121	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4251	Approved
0.6117	Remote Similarity	NPD4250	Approved
0.6098	Remote Similarity	NPD7604	Phase 2
0.6091	Remote Similarity	NPD4700	Approved
0.6071	Remote Similarity	NPD6647	Phase 2
0.6068	Remote Similarity	NPD6053	Discontinued
0.6067	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD7503	Approved
0.6061	Remote Similarity	NPD4695	Discontinued
0.6055	Remote Similarity	NPD6083	Phase 2
0.6055	Remote Similarity	NPD6084	Phase 2
0.6042	Remote Similarity	NPD8039	Approved
0.6019	Remote Similarity	NPD5695	Phase 3
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD4732	Discontinued
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD6317	Approved
0.5984	Remote Similarity	NPD6059	Approved
0.5984	Remote Similarity	NPD7319	Approved
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5048	Discontinued
0.5955	Remote Similarity	NPD4191	Approved
0.5955	Remote Similarity	NPD368	Approved
0.5955	Remote Similarity	NPD4193	Approved
0.5955	Remote Similarity	NPD4194	Approved
0.5955	Remote Similarity	NPD4192	Approved
0.5952	Remote Similarity	NPD8293	Discontinued
0.595	Remote Similarity	NPD6313	Approved
0.595	Remote Similarity	NPD6314	Approved
0.595	Remote Similarity	NPD7641	Discontinued
0.595	Remote Similarity	NPD6335	Approved
0.5948	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5207	Approved
0.5941	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7341	Phase 2
0.5929	Remote Similarity	NPD4754	Approved
0.5922	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.592	Remote Similarity	NPD8340	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