NPASS Compound

Structure

CID316844 OpenBabel06191716132D 25 26 0 0 1 0 0 0 0 0999 V2000 3.3878 0.9780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3878 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5408 -0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2015 2.0532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5105 3.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8706 1.3100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8414 3.7474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8469 -0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5616 0.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1504 4.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4890 0.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4669 0.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0257 0.3202 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 -0.5834 0.1511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1767 -0.7625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1597 0.8202 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8178 -0.6580 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4812 5.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8469 -0.4890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7903 6.3926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4969 5.2337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9643 0.7356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2934 -0.0035 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 6 1 0 0 0 0 4 5 1 0 0 0 0 4 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 9 15 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 15 21 1 6 0 0 0 16 10 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 13 1 6 0 0 0 17 19 1 0 0 0 0 18 14 1 6 0 0 0 18 24 1 0 0 0 0 19 14 1 6 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	373.405
LogP:	3.571
LogD:	3.076
LogS:	-3.76
# Rotatable Bonds:	12
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	5.022
Fsp3:	0.75
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:	-5.313
MDCK Permeability:	4.126505882595666e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.089
Human Intestinal Absorption (HIA):	0.767
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	92.8478012084961%
Volume Distribution (VD):	0.311
Pgp-substrate:	2.886444091796875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.769
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	4.002
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.407
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.369
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.692
Carcinogencity:	0.104
Eye Corrosion:	0.004
Eye Irritation:	0.033
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC316844

Natural Product ID:	NPC316844
*Common Name:**	Prostaglandin H2
IUPAC Name:	(Z)-7-[(1S,4R,5R,6R)-5-[(E,3S)-3-hydroxyoct-1-enyl]-2,3-dioxabicyclo[2.2.1]heptan-6-yl]hept-5-enoic acid
Synonyms:	Prostaglandin H2
Standard InCHIKey:	YIBNHAJFJUQSRA-YNNPMVKQSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
SMILES:	CCCCC[C@@H](/C=C/[C@H]1[C@@H]2OO[C@H]([C@@H]1C/C=CCCCC(=O)O)C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2074582
PubChem CID:	445049
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1024	Individual Protein	Solute carrier organic anion transporter family member 2A1	Rattus norvegicus	Ki	=	38.2	nM	PMID[508003]

☑ 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 NPC316844 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	168
0.1-0.2	1122
0.2-0.3	6703
0.3-0.4	16550
0.4-0.5	8860
0.5-0.6	7157
0.6-0.7	1977
0.7-0.8	132
0.8-0.85	11
0.85-0.9	9
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC260814
0.96	High Similarity	NPC27949
0.96	High Similarity	NPC39547
0.96	High Similarity	NPC323249
0.9231	High Similarity	NPC88735
0.9024	High Similarity	NPC316629
0.85	High Similarity	NPC201225
0.8415	Intermediate Similarity	NPC7414
0.8395	Intermediate Similarity	NPC115418
0.8354	Intermediate Similarity	NPC279537
0.8293	Intermediate Similarity	NPC47031
0.7711	Intermediate Similarity	NPC192006
0.7647	Intermediate Similarity	NPC191711
0.7625	Intermediate Similarity	NPC67076
0.7625	Intermediate Similarity	NPC319163
0.7619	Intermediate Similarity	NPC55304
0.7619	Intermediate Similarity	NPC164308
0.7619	Intermediate Similarity	NPC226226
0.759	Intermediate Similarity	NPC281296
0.7558	Intermediate Similarity	NPC474252
0.7553	Intermediate Similarity	NPC161493
0.7527	Intermediate Similarity	NPC170120
0.7527	Intermediate Similarity	NPC213698
0.75	Intermediate Similarity	NPC121200
0.7468	Intermediate Similarity	NPC224532
0.7447	Intermediate Similarity	NPC213078
0.7442	Intermediate Similarity	NPC52861
0.7442	Intermediate Similarity	NPC470241
0.7419	Intermediate Similarity	NPC127019
0.7412	Intermediate Similarity	NPC475210
0.7391	Intermediate Similarity	NPC475925
0.7386	Intermediate Similarity	NPC476804
0.7386	Intermediate Similarity	NPC475732
0.7381	Intermediate Similarity	NPC476439
0.7381	Intermediate Similarity	NPC474278
0.7363	Intermediate Similarity	NPC477215
0.7363	Intermediate Similarity	NPC476388
0.7356	Intermediate Similarity	NPC89555
0.7349	Intermediate Similarity	NPC199445
0.7342	Intermediate Similarity	NPC26500
0.7342	Intermediate Similarity	NPC99619
0.734	Intermediate Similarity	NPC54905
0.734	Intermediate Similarity	NPC52044
0.734	Intermediate Similarity	NPC314009
0.734	Intermediate Similarity	NPC67584
0.7333	Intermediate Similarity	NPC237540
0.732	Intermediate Similarity	NPC150923
0.7303	Intermediate Similarity	NPC255307
0.7292	Intermediate Similarity	NPC221615
0.7284	Intermediate Similarity	NPC4299
0.7284	Intermediate Similarity	NPC318766
0.7283	Intermediate Similarity	NPC472466
0.7273	Intermediate Similarity	NPC40746
0.7273	Intermediate Similarity	NPC69469
0.7273	Intermediate Similarity	NPC473390
0.7273	Intermediate Similarity	NPC472473
0.7273	Intermediate Similarity	NPC128246
0.7273	Intermediate Similarity	NPC131669
0.7273	Intermediate Similarity	NPC169575
0.7263	Intermediate Similarity	NPC24956
0.7263	Intermediate Similarity	NPC18019
0.7262	Intermediate Similarity	NPC469514
0.7245	Intermediate Similarity	NPC118405
0.7241	Intermediate Similarity	NPC24417
0.7241	Intermediate Similarity	NPC472471
0.7222	Intermediate Similarity	NPC477668
0.7222	Intermediate Similarity	NPC305475
0.7222	Intermediate Similarity	NPC184461
0.7222	Intermediate Similarity	NPC475461
0.7222	Intermediate Similarity	NPC476982
0.7204	Intermediate Similarity	NPC472468
0.7204	Intermediate Similarity	NPC45269
0.7195	Intermediate Similarity	NPC126061
0.7191	Intermediate Similarity	NPC165287
0.7191	Intermediate Similarity	NPC191476
0.7191	Intermediate Similarity	NPC158756
0.7191	Intermediate Similarity	NPC114979
0.7191	Intermediate Similarity	NPC96259
0.7191	Intermediate Similarity	NPC295799
0.7191	Intermediate Similarity	NPC141193
0.7188	Intermediate Similarity	NPC475894
0.7188	Intermediate Similarity	NPC107243
0.7188	Intermediate Similarity	NPC57416
0.7176	Intermediate Similarity	NPC320630
0.7176	Intermediate Similarity	NPC7563
0.7176	Intermediate Similarity	NPC116177
0.7174	Intermediate Similarity	NPC155479
0.716	Intermediate Similarity	NPC470436
0.716	Intermediate Similarity	NPC101622
0.7159	Intermediate Similarity	NPC229825
0.7158	Intermediate Similarity	NPC304886
0.7158	Intermediate Similarity	NPC472469
0.7143	Intermediate Similarity	NPC60718
0.7143	Intermediate Similarity	NPC312215
0.7143	Intermediate Similarity	NPC475405
0.7143	Intermediate Similarity	NPC321838
0.7143	Intermediate Similarity	NPC113639
0.7111	Intermediate Similarity	NPC165162
0.7111	Intermediate Similarity	NPC329738
0.7111	Intermediate Similarity	NPC470755
0.7111	Intermediate Similarity	NPC125290
0.7108	Intermediate Similarity	NPC477085
0.7108	Intermediate Similarity	NPC470435
0.7097	Intermediate Similarity	NPC473448
0.7097	Intermediate Similarity	NPC469368
0.7097	Intermediate Similarity	NPC46281
0.7097	Intermediate Similarity	NPC129419
0.7093	Intermediate Similarity	NPC11796
0.7093	Intermediate Similarity	NPC127526
0.7093	Intermediate Similarity	NPC108816
0.7093	Intermediate Similarity	NPC172066
0.7093	Intermediate Similarity	NPC218817
0.7093	Intermediate Similarity	NPC267231
0.7093	Intermediate Similarity	NPC93763
0.7089	Intermediate Similarity	NPC326268
0.7089	Intermediate Similarity	NPC136164
0.7089	Intermediate Similarity	NPC318420
0.7089	Intermediate Similarity	NPC245947
0.7089	Intermediate Similarity	NPC255863
0.7079	Intermediate Similarity	NPC477667
0.7079	Intermediate Similarity	NPC111409
0.7079	Intermediate Similarity	NPC116543
0.7065	Intermediate Similarity	NPC48866
0.7065	Intermediate Similarity	NPC247406
0.7065	Intermediate Similarity	NPC217983
0.7065	Intermediate Similarity	NPC476805
0.7065	Intermediate Similarity	NPC294480
0.7065	Intermediate Similarity	NPC476803
0.7065	Intermediate Similarity	NPC207114
0.7065	Intermediate Similarity	NPC475712
0.7059	Intermediate Similarity	NPC68819
0.7059	Intermediate Similarity	NPC310643
0.7059	Intermediate Similarity	NPC474447
0.7053	Intermediate Similarity	NPC262133
0.7053	Intermediate Similarity	NPC7165
0.7053	Intermediate Similarity	NPC323008
0.7053	Intermediate Similarity	NPC470010
0.7053	Intermediate Similarity	NPC470013
0.7053	Intermediate Similarity	NPC198853
0.7053	Intermediate Similarity	NPC472467
0.7045	Intermediate Similarity	NPC126248
0.7045	Intermediate Similarity	NPC112868
0.7037	Intermediate Similarity	NPC273508
0.7037	Intermediate Similarity	NPC209327
0.7033	Intermediate Similarity	NPC469910
0.7033	Intermediate Similarity	NPC212843
0.7033	Intermediate Similarity	NPC278283
0.7024	Intermediate Similarity	NPC474280
0.7024	Intermediate Similarity	NPC227396
0.7021	Intermediate Similarity	NPC57304
0.7021	Intermediate Similarity	NPC133888
0.7021	Intermediate Similarity	NPC29821
0.7021	Intermediate Similarity	NPC171360
0.7021	Intermediate Similarity	NPC63193
0.7021	Intermediate Similarity	NPC293001
0.7021	Intermediate Similarity	NPC35959
0.7013	Intermediate Similarity	NPC243532
0.7013	Intermediate Similarity	NPC328311
0.7013	Intermediate Similarity	NPC327112
0.7011	Intermediate Similarity	NPC167881
0.7011	Intermediate Similarity	NPC98557
0.7011	Intermediate Similarity	NPC89128
0.7011	Intermediate Similarity	NPC321728
0.701	Intermediate Similarity	NPC472290
0.701	Intermediate Similarity	NPC469432
0.701	Intermediate Similarity	NPC87090
0.7	Intermediate Similarity	NPC474775
0.7	Intermediate Similarity	NPC165064
0.7	Intermediate Similarity	NPC156485
0.6989	Remote Similarity	NPC310236
0.6989	Remote Similarity	NPC268298
0.6989	Remote Similarity	NPC232747
0.6988	Remote Similarity	NPC477086
0.6988	Remote Similarity	NPC477087
0.6988	Remote Similarity	NPC472254
0.6979	Remote Similarity	NPC476487
0.6979	Remote Similarity	NPC476488
0.6977	Remote Similarity	NPC97516
0.6974	Remote Similarity	NPC226848
0.697	Remote Similarity	NPC477950
0.6966	Remote Similarity	NPC472465
0.6962	Remote Similarity	NPC470320
0.6961	Remote Similarity	NPC64844
0.6961	Remote Similarity	NPC42847
0.6957	Remote Similarity	NPC128644
0.6957	Remote Similarity	NPC86005
0.6957	Remote Similarity	NPC477959
0.6951	Remote Similarity	NPC236208
0.6947	Remote Similarity	NPC243866
0.6947	Remote Similarity	NPC472942
0.6947	Remote Similarity	NPC125180
0.6939	Remote Similarity	NPC166745
0.6939	Remote Similarity	NPC141191
0.6939	Remote Similarity	NPC48647
0.6939	Remote Similarity	NPC235464
0.6939	Remote Similarity	NPC197386
0.6932	Remote Similarity	NPC472470
0.6932	Remote Similarity	NPC51507
0.6923	Remote Similarity	NPC269638
0.6923	Remote Similarity	NPC78089

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 NPC316844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	138
0.1-0.2	1842
0.2-0.3	4186
0.3-0.4	2150
0.4-0.5	472
0.5-0.6	310
0.6-0.7	26
0.7-0.8	8
0.8-0.85	8
0.85-0.9	4
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.96	High Similarity	NPD4271	Approved
0.96	High Similarity	NPD4268	Approved
0.9351	High Similarity	NPD4819	Approved
0.9351	High Similarity	NPD4821	Approved
0.9351	High Similarity	NPD4822	Approved
0.9351	High Similarity	NPD4820	Approved
0.9351	High Similarity	NPD5790	Clinical (unspecified phase)
0.9024	High Similarity	NPD4251	Approved
0.9024	High Similarity	NPD4250	Approved
0.8902	High Similarity	NPD4249	Approved
0.8537	High Similarity	NPD5362	Discontinued
0.8537	High Similarity	NPD5332	Approved
0.8537	High Similarity	NPD5331	Approved
0.8519	High Similarity	NPD4790	Discontinued
0.8415	Intermediate Similarity	NPD4270	Approved
0.8415	Intermediate Similarity	NPD4269	Approved
0.8395	Intermediate Similarity	NPD5368	Approved
0.8395	Intermediate Similarity	NPD4252	Approved
0.8193	Intermediate Similarity	NPD6435	Approved
0.8118	Intermediate Similarity	NPD5363	Approved
0.8095	Intermediate Similarity	NPD7154	Phase 3
0.8023	Intermediate Similarity	NPD5786	Approved
0.7927	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5369	Approved
0.7701	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5785	Approved
0.7191	Intermediate Similarity	NPD5766	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5370	Suspended
0.7172	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7637	Suspended
0.7021	Intermediate Similarity	NPD4810	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7983	Approved
0.6771	Remote Similarity	NPD5779	Approved
0.6771	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3198	Approved
0.6636	Remote Similarity	NPD6053	Discontinued
0.6635	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6420	Discontinued
0.6562	Remote Similarity	NPD46	Approved
0.6562	Remote Similarity	NPD6698	Approved
0.6543	Remote Similarity	NPD3197	Phase 1
0.6535	Remote Similarity	NPD7640	Approved
0.6535	Remote Similarity	NPD7639	Approved
0.6505	Remote Similarity	NPD5765	Approved
0.6476	Remote Similarity	NPD6685	Approved
0.6458	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6101	Approved
0.6436	Remote Similarity	NPD7638	Approved
0.6429	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD7839	Suspended
0.6392	Remote Similarity	NPD7838	Discovery
0.6374	Remote Similarity	NPD7514	Phase 3
0.6337	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD6083	Phase 2
0.6333	Remote Similarity	NPD7145	Approved
0.6327	Remote Similarity	NPD6411	Approved
0.6304	Remote Similarity	NPD6902	Approved
0.6296	Remote Similarity	NPD6371	Approved
0.6289	Remote Similarity	NPD1695	Approved
0.6277	Remote Similarity	NPD3133	Approved
0.6277	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4786	Approved
0.6277	Remote Similarity	NPD3666	Approved
0.6277	Remote Similarity	NPD3665	Phase 1
0.6275	Remote Similarity	NPD4225	Approved
0.6264	Remote Similarity	NPD6929	Approved
0.6263	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7320	Approved
0.6262	Remote Similarity	NPD6899	Approved
0.6262	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.6237	Remote Similarity	NPD5209	Approved
0.6237	Remote Similarity	NPD3667	Approved
0.6234	Remote Similarity	NPD4266	Approved
0.6234	Remote Similarity	NPD3196	Approved
0.6234	Remote Similarity	NPD3194	Approved
0.6234	Remote Similarity	NPD3195	Phase 2
0.6226	Remote Similarity	NPD6675	Approved
0.6226	Remote Similarity	NPD5739	Approved
0.6226	Remote Similarity	NPD6402	Approved
0.6226	Remote Similarity	NPD7128	Approved
0.6222	Remote Similarity	NPD6925	Approved
0.6222	Remote Similarity	NPD5776	Phase 2
0.6196	Remote Similarity	NPD6931	Approved
0.6196	Remote Similarity	NPD6930	Phase 2
0.6196	Remote Similarity	NPD7332	Phase 2
0.6186	Remote Similarity	NPD6903	Approved
0.617	Remote Similarity	NPD6695	Phase 3
0.6168	Remote Similarity	NPD5697	Approved
0.6162	Remote Similarity	NPD5281	Approved
0.6162	Remote Similarity	NPD5284	Approved
0.6154	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6883	Approved
0.6147	Remote Similarity	NPD7102	Approved
0.6147	Remote Similarity	NPD7290	Approved
0.6146	Remote Similarity	NPD5330	Approved
0.6146	Remote Similarity	NPD7146	Approved
0.6146	Remote Similarity	NPD6684	Approved
0.6146	Remote Similarity	NPD7521	Approved
0.6146	Remote Similarity	NPD7334	Approved
0.6146	Remote Similarity	NPD6409	Approved
0.6139	Remote Similarity	NPD5695	Phase 3
0.6132	Remote Similarity	NPD5141	Approved
0.6122	Remote Similarity	NPD4753	Phase 2
0.6117	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD3172	Approved
0.6098	Remote Similarity	NPD368	Approved
0.6092	Remote Similarity	NPD7143	Approved
0.6092	Remote Similarity	NPD7144	Approved
0.6091	Remote Similarity	NPD6650	Approved
0.6091	Remote Similarity	NPD8130	Phase 1
0.6091	Remote Similarity	NPD6617	Approved
0.6091	Remote Similarity	NPD6649	Approved
0.6091	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6847	Approved
0.6091	Remote Similarity	NPD6869	Approved
0.6067	Remote Similarity	NPD6924	Approved
0.6067	Remote Similarity	NPD6926	Approved
0.6058	Remote Similarity	NPD5286	Approved
0.6058	Remote Similarity	NPD5285	Approved
0.6058	Remote Similarity	NPD4696	Approved
0.6055	Remote Similarity	NPD6372	Approved
0.6055	Remote Similarity	NPD6013	Approved
0.6055	Remote Similarity	NPD6014	Approved
0.6055	Remote Similarity	NPD6373	Approved
0.6055	Remote Similarity	NPD6012	Approved
0.6044	Remote Similarity	NPD6932	Approved
0.604	Remote Similarity	NPD5282	Discontinued
0.6038	Remote Similarity	NPD6647	Phase 2
0.6036	Remote Similarity	NPD6912	Phase 3
0.6036	Remote Similarity	NPD8297	Approved
0.6036	Remote Similarity	NPD6882	Approved
0.6023	Remote Similarity	NPD7150	Approved
0.6023	Remote Similarity	NPD7151	Approved
0.6023	Remote Similarity	NPD7152	Approved
0.602	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5701	Approved
0.6019	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD8264	Approved
0.6	Remote Similarity	NPD5344	Discontinued
0.598	Remote Similarity	NPD5210	Approved
0.598	Remote Similarity	NPD4629	Approved
0.5978	Remote Similarity	NPD3732	Approved
0.5977	Remote Similarity	NPD6923	Approved
0.5977	Remote Similarity	NPD6922	Approved
0.5965	Remote Similarity	NPD7115	Discovery
0.5963	Remote Similarity	NPD6011	Approved
0.5962	Remote Similarity	NPD5696	Approved
0.596	Remote Similarity	NPD6051	Approved
0.5943	Remote Similarity	NPD4633	Approved
0.5943	Remote Similarity	NPD5224	Approved
0.5943	Remote Similarity	NPD7632	Discontinued
0.5943	Remote Similarity	NPD5226	Approved
0.5943	Remote Similarity	NPD5225	Approved
0.5941	Remote Similarity	NPD4202	Approved
0.5934	Remote Similarity	NPD6933	Approved
0.5918	Remote Similarity	NPD7524	Approved
0.5918	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7750	Discontinued
0.5905	Remote Similarity	NPD4700	Approved
0.5902	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5175	Approved
0.5888	Remote Similarity	NPD5174	Approved
0.5876	Remote Similarity	NPD6893	Approved
0.5876	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6412	Phase 2
0.587	Remote Similarity	NPD4756	Discovery
0.5851	Remote Similarity	NPD7525	Registered
0.5849	Remote Similarity	NPD5223	Approved
0.5844	Remote Similarity	NPD28	Approved
0.5844	Remote Similarity	NPD29	Approved
0.5842	Remote Similarity	NPD6079	Approved
0.5842	Remote Similarity	NPD7515	Phase 2
0.5833	Remote Similarity	NPD6110	Phase 1
0.5825	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6942	Approved
0.5824	Remote Similarity	NPD7339	Approved
0.5824	Remote Similarity	NPD8039	Approved
0.582	Remote Similarity	NPD6362	Approved
0.5818	Remote Similarity	NPD6406	Approved
0.5818	Remote Similarity	NPD6686	Approved
0.5816	Remote Similarity	NPD6422	Discontinued
0.5816	Remote Similarity	NPD3618	Phase 1
0.5816	Remote Similarity	NPD5279	Phase 3
0.5804	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5328	Approved
0.5789	Remote Similarity	NPD6898	Phase 1
0.5789	Remote Similarity	NPD3173	Approved
0.578	Remote Similarity	NPD6008	Approved
0.5773	Remote Similarity	NPD3668	Phase 3
0.5763	Remote Similarity	NPD8513	Phase 3
0.5763	Remote Similarity	NPD8516	Approved
0.5763	Remote Similarity	NPD8515	Approved
0.5763	Remote Similarity	NPD8517	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