NPASS Compound

Structure

CID47031 OpenBabel06191715382D 25 25 0 0 1 0 0 0 0 0999 V2000 7.3292 -2.8180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3347 -2.9225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7469 -2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9328 3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7524 -2.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1896 4.5546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1646 -1.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3975 5.5328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1701 -1.5135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 1 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 0.6544 6.2019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7634 -2.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2967 5.8929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8623 7.1801 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 1 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 14 18 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 6 0 0 0 16 10 1 6 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 13 1 1 0 0 0 17 19 1 0 0 0 0 18 22 1 6 0 0 0 19 23 2 0 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.24
Volume:	381.961
LogP:	3.459
LogD:	2.236
LogS:	-3.268
# Rotatable Bonds:	13
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	3.773
Fsp3:	0.8
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:	-5.164
MDCK Permeability:	3.1739200494484976e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.982
Human Intestinal Absorption (HIA):	0.623
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.563
Plasma Protein Binding (PPB):	92.08980560302734%
Volume Distribution (VD):	0.324
Pgp-substrate:	7.603851795196533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.296
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.042

ADMET: Excretion

Clearance (CL):	9.328
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.073
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.405
Skin Sensitization:	0.202
Carcinogencity:	0.112
Eye Corrosion:	0.047
Eye Irritation:	0.125
Respiratory Toxicity:	0.249

Download Data

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

Natural Product: NPC47031

Natural Product ID:	NPC47031
*Common Name:**	Prostaglandin D1
IUPAC Name:	7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]heptanoic acid
Synonyms:	Prostaglandin D1
Standard InCHIKey:	CIMMACURCPXICP-PNQRDDRVSA-N
Standard InCHI:	InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-18,21-22H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,18-/m0/s1
SMILES:	CCCCC[C@@H](/C=C/[C@H]1C(=O)C[C@@H]([C@@H]1CCCCCCC(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2075005
PubChem CID:	5280936
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

☑ 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	=	162.0	nM	PMID[537057]

☑ 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 NPC47031 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	162
0.1-0.2	1077
0.2-0.3	5780
0.3-0.4	15192
0.4-0.5	9509
0.5-0.6	6921
0.6-0.7	3498
0.7-0.8	529
0.8-0.85	14
0.85-0.9	10
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC7414
0.9733	High Similarity	NPC201225
0.9605	High Similarity	NPC115418
0.9333	High Similarity	NPC279537
0.8987	High Similarity	NPC88735
0.8734	High Similarity	NPC164308
0.8608	High Similarity	NPC27949
0.8608	High Similarity	NPC323249
0.8608	High Similarity	NPC192006
0.8608	High Similarity	NPC39547
0.8608	High Similarity	NPC260814
0.8293	Intermediate Similarity	NPC316844
0.8118	Intermediate Similarity	NPC125290
0.8025	Intermediate Similarity	NPC281296
0.7935	Intermediate Similarity	NPC107243
0.7927	Intermediate Similarity	NPC218817
0.7927	Intermediate Similarity	NPC121200
0.7927	Intermediate Similarity	NPC11796
0.7912	Intermediate Similarity	NPC476487
0.7912	Intermediate Similarity	NPC54905
0.7912	Intermediate Similarity	NPC476488
0.7912	Intermediate Similarity	NPC314009
0.7857	Intermediate Similarity	NPC470241
0.7848	Intermediate Similarity	NPC319163
0.7848	Intermediate Similarity	NPC67076
0.7778	Intermediate Similarity	NPC45269
0.7778	Intermediate Similarity	NPC199445
0.7753	Intermediate Similarity	NPC155479
0.775	Intermediate Similarity	NPC275098
0.7742	Intermediate Similarity	NPC57416
0.7742	Intermediate Similarity	NPC475894
0.7727	Intermediate Similarity	NPC312215
0.7727	Intermediate Similarity	NPC316629
0.7717	Intermediate Similarity	NPC263347
0.7701	Intermediate Similarity	NPC261380
0.7692	Intermediate Similarity	NPC319007
0.7692	Intermediate Similarity	NPC243866
0.7683	Intermediate Similarity	NPC469514
0.7683	Intermediate Similarity	NPC469646
0.7674	Intermediate Similarity	NPC69469
0.7667	Intermediate Similarity	NPC145666
0.7667	Intermediate Similarity	NPC46281
0.7654	Intermediate Similarity	NPC227396
0.7647	Intermediate Similarity	NPC191711
0.764	Intermediate Similarity	NPC247406
0.764	Intermediate Similarity	NPC48866
0.764	Intermediate Similarity	NPC294480
0.7634	Intermediate Similarity	NPC155676
0.7619	Intermediate Similarity	NPC472013
0.7619	Intermediate Similarity	NPC476624
0.7619	Intermediate Similarity	NPC89128
0.7614	Intermediate Similarity	NPC212843
0.7609	Intermediate Similarity	NPC7165
0.7586	Intermediate Similarity	NPC165064
0.7582	Intermediate Similarity	NPC154101
0.7564	Intermediate Similarity	NPC99619
0.7564	Intermediate Similarity	NPC60120
0.7564	Intermediate Similarity	NPC26500
0.7558	Intermediate Similarity	NPC85772
0.7556	Intermediate Similarity	NPC472970
0.7556	Intermediate Similarity	NPC472971
0.7556	Intermediate Similarity	NPC54689
0.7556	Intermediate Similarity	NPC214387
0.7556	Intermediate Similarity	NPC2983
0.7556	Intermediate Similarity	NPC170775
0.7556	Intermediate Similarity	NPC310236
0.7556	Intermediate Similarity	NPC476388
0.7556	Intermediate Similarity	NPC477215
0.7553	Intermediate Similarity	NPC477949
0.7532	Intermediate Similarity	NPC245947
0.7532	Intermediate Similarity	NPC136164
0.7532	Intermediate Similarity	NPC255863
0.7528	Intermediate Similarity	NPC237540
0.7528	Intermediate Similarity	NPC96496
0.7528	Intermediate Similarity	NPC86005
0.7528	Intermediate Similarity	NPC477959
0.7527	Intermediate Similarity	NPC472469
0.75	Intermediate Similarity	NPC28887
0.75	Intermediate Similarity	NPC477950
0.75	Intermediate Similarity	NPC152897
0.75	Intermediate Similarity	NPC127526
0.75	Intermediate Similarity	NPC476627
0.75	Intermediate Similarity	NPC42526
0.75	Intermediate Similarity	NPC66429
0.75	Intermediate Similarity	NPC282524
0.7474	Intermediate Similarity	NPC197386
0.7474	Intermediate Similarity	NPC235464
0.7474	Intermediate Similarity	NPC48647
0.7474	Intermediate Similarity	NPC166745
0.7473	Intermediate Similarity	NPC477149
0.7473	Intermediate Similarity	NPC123854
0.7473	Intermediate Similarity	NPC320026
0.7473	Intermediate Similarity	NPC477147
0.7471	Intermediate Similarity	NPC62214
0.7471	Intermediate Similarity	NPC477785
0.7471	Intermediate Similarity	NPC477784
0.7471	Intermediate Similarity	NPC477786
0.747	Intermediate Similarity	NPC474447
0.7468	Intermediate Similarity	NPC476614
0.7468	Intermediate Similarity	NPC224532
0.7447	Intermediate Similarity	NPC29152
0.7447	Intermediate Similarity	NPC301534
0.7447	Intermediate Similarity	NPC250757
0.7444	Intermediate Similarity	NPC193843
0.7444	Intermediate Similarity	NPC476805
0.7444	Intermediate Similarity	NPC476803
0.7444	Intermediate Similarity	NPC249889
0.7444	Intermediate Similarity	NPC183546
0.7442	Intermediate Similarity	NPC52861
0.7439	Intermediate Similarity	NPC472966
0.7423	Intermediate Similarity	NPC204450
0.7423	Intermediate Similarity	NPC118405
0.7423	Intermediate Similarity	NPC195290
0.7419	Intermediate Similarity	NPC65829
0.7419	Intermediate Similarity	NPC53685
0.7416	Intermediate Similarity	NPC469483
0.7416	Intermediate Similarity	NPC315395
0.7416	Intermediate Similarity	NPC469994
0.7416	Intermediate Similarity	NPC261721
0.7416	Intermediate Similarity	NPC476982
0.7416	Intermediate Similarity	NPC316426
0.7412	Intermediate Similarity	NPC308545
0.7412	Intermediate Similarity	NPC55304
0.7412	Intermediate Similarity	NPC7232
0.7412	Intermediate Similarity	NPC82488
0.7412	Intermediate Similarity	NPC226226
0.7407	Intermediate Similarity	NPC126061
0.7403	Intermediate Similarity	NPC470320
0.7396	Intermediate Similarity	NPC477521
0.7396	Intermediate Similarity	NPC218383
0.7391	Intermediate Similarity	NPC111114
0.7391	Intermediate Similarity	NPC261607
0.7391	Intermediate Similarity	NPC300312
0.7386	Intermediate Similarity	NPC158756
0.7386	Intermediate Similarity	NPC96259
0.7386	Intermediate Similarity	NPC141193
0.7386	Intermediate Similarity	NPC476804
0.7386	Intermediate Similarity	NPC295799
0.7381	Intermediate Similarity	NPC476439
0.7381	Intermediate Similarity	NPC116177
0.7381	Intermediate Similarity	NPC320630
0.7381	Intermediate Similarity	NPC276769
0.7381	Intermediate Similarity	NPC7563
0.7375	Intermediate Similarity	NPC469677
0.7375	Intermediate Similarity	NPC143396
0.7368	Intermediate Similarity	NPC469432
0.7368	Intermediate Similarity	NPC156546
0.7368	Intermediate Similarity	NPC174560
0.7368	Intermediate Similarity	NPC125312
0.7368	Intermediate Similarity	NPC475438
0.7368	Intermediate Similarity	NPC53844
0.7363	Intermediate Similarity	NPC232747
0.7356	Intermediate Similarity	NPC89555
0.7356	Intermediate Similarity	NPC133844
0.7356	Intermediate Similarity	NPC20262
0.7356	Intermediate Similarity	NPC256750
0.7349	Intermediate Similarity	NPC60718
0.7349	Intermediate Similarity	NPC474011
0.7349	Intermediate Similarity	NPC251435
0.7347	Intermediate Similarity	NPC236390
0.7347	Intermediate Similarity	NPC475050
0.734	Intermediate Similarity	NPC20546
0.734	Intermediate Similarity	NPC88310
0.734	Intermediate Similarity	NPC469599
0.734	Intermediate Similarity	NPC476174
0.7333	Intermediate Similarity	NPC287079
0.7333	Intermediate Similarity	NPC128644
0.7333	Intermediate Similarity	NPC471738
0.7333	Intermediate Similarity	NPC72513
0.7333	Intermediate Similarity	NPC317590
0.7333	Intermediate Similarity	NPC179659
0.7327	Intermediate Similarity	NPC475941
0.7327	Intermediate Similarity	NPC474901
0.7326	Intermediate Similarity	NPC45495
0.7326	Intermediate Similarity	NPC200446
0.732	Intermediate Similarity	NPC224720
0.732	Intermediate Similarity	NPC476240
0.732	Intermediate Similarity	NPC472924
0.732	Intermediate Similarity	NPC476223
0.7317	Intermediate Similarity	NPC474543
0.7317	Intermediate Similarity	NPC167145
0.7317	Intermediate Similarity	NPC238425
0.7317	Intermediate Similarity	NPC472018
0.7317	Intermediate Similarity	NPC321017
0.7312	Intermediate Similarity	NPC470375
0.7312	Intermediate Similarity	NPC470376
0.7312	Intermediate Similarity	NPC37816
0.7312	Intermediate Similarity	NPC469692
0.7312	Intermediate Similarity	NPC469645
0.7312	Intermediate Similarity	NPC472942
0.7308	Intermediate Similarity	NPC318420
0.7308	Intermediate Similarity	NPC326268
0.7303	Intermediate Similarity	NPC471224
0.7303	Intermediate Similarity	NPC269638
0.7303	Intermediate Similarity	NPC474083
0.7303	Intermediate Similarity	NPC165162
0.7303	Intermediate Similarity	NPC255307
0.7303	Intermediate Similarity	NPC476628
0.7303	Intermediate Similarity	NPC471344
0.7303	Intermediate Similarity	NPC475206

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 NPC47031 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	1789
0.2-0.3	3955
0.3-0.4	2221
0.4-0.5	582
0.5-0.6	308
0.6-0.7	125
0.7-0.8	15
0.8-0.85	4
0.85-0.9	7
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9868	High Similarity	NPD4269	Approved
0.9868	High Similarity	NPD4270	Approved
0.9605	High Similarity	NPD4252	Approved
0.9494	High Similarity	NPD5363	Approved
0.9375	High Similarity	NPD5786	Approved
0.9231	High Similarity	NPD5369	Approved
0.8929	High Similarity	NPD5785	Approved
0.8846	High Similarity	NPD5784	Clinical (unspecified phase)
0.8765	High Similarity	NPD5362	Discontinued
0.8625	High Similarity	NPD4821	Approved
0.8625	High Similarity	NPD4819	Approved
0.8625	High Similarity	NPD5368	Approved
0.8625	High Similarity	NPD4822	Approved
0.8625	High Similarity	NPD4820	Approved
0.8608	High Similarity	NPD4268	Approved
0.8608	High Similarity	NPD4271	Approved
0.8415	Intermediate Similarity	NPD6435	Approved
0.8395	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5331	Approved
0.8313	Intermediate Similarity	NPD5332	Approved
0.8293	Intermediate Similarity	NPD4790	Discontinued
0.8095	Intermediate Similarity	NPD7154	Phase 3
0.7955	Intermediate Similarity	NPD5370	Suspended
0.7778	Intermediate Similarity	NPD4810	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4250	Approved
0.7727	Intermediate Similarity	NPD4251	Approved
0.7701	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4249	Approved
0.7333	Intermediate Similarity	NPD3198	Approved
0.7312	Intermediate Similarity	NPD5779	Approved
0.7312	Intermediate Similarity	NPD5778	Approved
0.7204	Intermediate Similarity	NPD7983	Approved
0.7204	Intermediate Similarity	NPD7637	Suspended
0.7013	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD3133	Approved
0.7	Intermediate Similarity	NPD5766	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6101	Approved
0.6979	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3197	Phase 1
0.6947	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD6371	Approved
0.6907	Remote Similarity	NPD7839	Suspended
0.6848	Remote Similarity	NPD5330	Approved
0.6848	Remote Similarity	NPD7521	Approved
0.6848	Remote Similarity	NPD6684	Approved
0.6848	Remote Similarity	NPD7146	Approved
0.6848	Remote Similarity	NPD7334	Approved
0.6848	Remote Similarity	NPD6409	Approved
0.6842	Remote Similarity	NPD5284	Approved
0.6842	Remote Similarity	NPD6411	Approved
0.6842	Remote Similarity	NPD5281	Approved
0.6837	Remote Similarity	NPD6084	Phase 2
0.6837	Remote Similarity	NPD6083	Phase 2
0.6813	Remote Similarity	NPD4786	Approved
0.6796	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5209	Approved
0.6778	Remote Similarity	NPD3667	Approved
0.6762	Remote Similarity	NPD6420	Discontinued
0.6707	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4238	Approved
0.6705	Remote Similarity	NPD3732	Approved
0.6705	Remote Similarity	NPD4802	Phase 2
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6903	Approved
0.67	Remote Similarity	NPD7640	Approved
0.67	Remote Similarity	NPD7639	Approved
0.6697	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD3196	Approved
0.6667	Remote Similarity	NPD3195	Phase 2
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD3194	Approved
0.6667	Remote Similarity	NPD4266	Approved
0.6633	Remote Similarity	NPD5210	Approved
0.6633	Remote Similarity	NPD4629	Approved
0.6633	Remote Similarity	NPD5695	Phase 3
0.6632	Remote Similarity	NPD4753	Phase 2
0.66	Remote Similarity	NPD7638	Approved
0.66	Remote Similarity	NPD5696	Approved
0.6571	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD46	Approved
0.6562	Remote Similarity	NPD6698	Approved
0.6542	Remote Similarity	NPD6649	Approved
0.6542	Remote Similarity	NPD6650	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6533	Remote Similarity	NPD3172	Approved
0.6509	Remote Similarity	NPD6372	Approved
0.6509	Remote Similarity	NPD6373	Approved
0.6505	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6079	Approved
0.6495	Remote Similarity	NPD7515	Phase 2
0.6489	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5279	Phase 3
0.6476	Remote Similarity	NPD5697	Approved
0.6458	Remote Similarity	NPD5328	Approved
0.6449	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD7290	Approved
0.6449	Remote Similarity	NPD7102	Approved
0.6442	Remote Similarity	NPD5141	Approved
0.6436	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD4202	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD6011	Approved
0.6413	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4223	Phase 3
0.6413	Remote Similarity	NPD4221	Approved
0.6389	Remote Similarity	NPD6847	Approved
0.6389	Remote Similarity	NPD6617	Approved
0.6389	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD8130	Phase 1
0.6386	Remote Similarity	NPD7331	Phase 2
0.6383	Remote Similarity	NPD1694	Approved
0.6383	Remote Similarity	NPD5329	Approved
0.6383	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5285	Approved
0.6373	Remote Similarity	NPD5286	Approved
0.6373	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD5282	Discontinued
0.6364	Remote Similarity	NPD8039	Approved
0.6355	Remote Similarity	NPD6013	Approved
0.6355	Remote Similarity	NPD6014	Approved
0.6355	Remote Similarity	NPD6012	Approved
0.6354	Remote Similarity	NPD5737	Approved
0.6354	Remote Similarity	NPD6672	Approved
0.6344	Remote Similarity	NPD4788	Approved
0.6337	Remote Similarity	NPD4755	Approved
0.633	Remote Similarity	NPD6882	Approved
0.633	Remote Similarity	NPD6053	Discontinued
0.633	Remote Similarity	NPD8297	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD5690	Phase 2
0.6316	Remote Similarity	NPD6098	Approved
0.6311	Remote Similarity	NPD5223	Approved
0.6303	Remote Similarity	NPD6085	Phase 2
0.6303	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6080	Approved
0.6289	Remote Similarity	NPD6673	Approved
0.6289	Remote Similarity	NPD6904	Approved
0.6277	Remote Similarity	NPD4197	Approved
0.6277	Remote Similarity	NPD3668	Phase 3
0.6267	Remote Similarity	NPD29	Approved
0.6267	Remote Similarity	NPD28	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD4633	Approved
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5222	Approved
0.6238	Remote Similarity	NPD4697	Phase 3
0.6238	Remote Similarity	NPD5221	Approved
0.6238	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5207	Approved
0.6222	Remote Similarity	NPD4756	Discovery
0.6214	Remote Similarity	NPD4700	Approved
0.6204	Remote Similarity	NPD6413	Approved
0.62	Remote Similarity	NPD7748	Approved
0.6196	Remote Similarity	NPD7514	Phase 3
0.619	Remote Similarity	NPD5765	Approved
0.619	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD5174	Approved
0.619	Remote Similarity	NPD6647	Phase 2
0.6186	Remote Similarity	NPD4518	Approved
0.6176	Remote Similarity	NPD7902	Approved
0.6176	Remote Similarity	NPD5173	Approved
0.617	Remote Similarity	NPD6110	Phase 1
0.6168	Remote Similarity	NPD6412	Phase 2
0.6168	Remote Similarity	NPD6685	Approved
0.6162	Remote Similarity	NPD6050	Approved
0.6162	Remote Similarity	NPD8035	Phase 2
0.6162	Remote Similarity	NPD8034	Phase 2
0.6162	Remote Similarity	NPD5693	Phase 1
0.6162	Remote Similarity	NPD5694	Approved
0.6154	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7145	Approved
0.6147	Remote Similarity	NPD4634	Approved
0.6146	Remote Similarity	NPD5205	Approved
0.6146	Remote Similarity	NPD4688	Approved
0.6146	Remote Similarity	NPD4693	Phase 3
0.6146	Remote Similarity	NPD5280	Approved
0.6146	Remote Similarity	NPD4519	Discontinued
0.6146	Remote Similarity	NPD4623	Approved
0.6146	Remote Similarity	NPD4138	Approved
0.6146	Remote Similarity	NPD4689	Approved
0.6146	Remote Similarity	NPD4690	Approved
0.6146	Remote Similarity	NPD4694	Approved
0.6129	Remote Similarity	NPD6902	Approved
0.6126	Remote Similarity	NPD4632	Approved
0.6122	Remote Similarity	NPD1695	Approved
0.6122	Remote Similarity	NPD6051	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