NPASS Compound

Structure

CID201225 OpenBabel06191715592D 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 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 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:	352.22
Volume:	379.325
LogP:	2.213
LogD:	1.132
LogS:	-3.281
# Rotatable Bonds:	12
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	3.966
Fsp3:	0.7
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:	-5.315
MDCK Permeability:	2.917290294135455e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.314
Human Intestinal Absorption (HIA):	0.68
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.32
Plasma Protein Binding (PPB):	89.31596374511719%
Volume Distribution (VD):	0.27
Pgp-substrate:	11.180803298950195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.627
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.225
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	8.95
Half-life (T1/2):	0.933

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.783
Skin Sensitization:	0.288
Carcinogencity:	0.188
Eye Corrosion:	0.013
Eye Irritation:	0.06
Respiratory Toxicity:	0.225

Download Data

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

Natural Product: NPC201225

Natural Product ID:	NPC201225
*Common Name:**	Prostaglandin D2
IUPAC Name:	(Z)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enoic acid
Synonyms:
Standard InCHIKey:	BHMBVRSPMRCCGG-OUTUXVNYSA-N
Standard InCHI:	InChI=1S/C20H32O5/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/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
SMILES:	CCCCC[C@@H](/C=C/[C@H]1C(=O)C[C@@H]([C@@H]1C/C=CCCCC(=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1235252
PubChem CID:	448457
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	3
Others	3
Potency	1

Activity Type	# Activity
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1025	Individual Protein	Solute carrier organic anion transporter family member 2B1	Rattus norvegicus	Km	=	35.5	nM	PMID[533774]
NPT1023	Individual Protein	Solute carrier organic anion transporter family member 3A1	Homo sapiens	Activity	=	30.0	%	PMID[533775]
NPT1029	Individual Protein	Solute carrier organic anion transporter family member 2A1	Homo sapiens	K1/2	=	0.083	uM	PMID[533776]
NPT1029	Individual Protein	Solute carrier organic anion transporter family member 2A1	Homo sapiens	Ki	=	38.0	nM	PMID[533777]
NPT1024	Individual Protein	Solute carrier organic anion transporter family member 2A1	Rattus norvegicus	Ki	=	45.0	nM	PMID[533777]
NPT2775	Individual Protein	Solute carrier organic anion transporter family member 2A1	Mus musculus	Ki	=	98.0	nM	PMID[533777]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	35481.3	nM	PMID[533773]

☑ 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 NPC201225 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	157
0.1-0.2	1123
0.2-0.3	6102
0.3-0.4	15991
0.4-0.5	9027
0.5-0.6	6881
0.6-0.7	3055
0.7-0.8	333
0.8-0.85	13
0.85-0.9	9
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC47031
0.9605	High Similarity	NPC7414
0.96	High Similarity	NPC115418
0.9067	High Similarity	NPC279537
0.8831	High Similarity	NPC323249
0.8831	High Similarity	NPC260814
0.8831	High Similarity	NPC27949
0.8831	High Similarity	NPC39547
0.8734	High Similarity	NPC88735
0.8718	High Similarity	NPC164308
0.85	High Similarity	NPC316844
0.8354	Intermediate Similarity	NPC192006
0.8052	Intermediate Similarity	NPC319163
0.8052	Intermediate Similarity	NPC67076
0.7907	Intermediate Similarity	NPC316629
0.7882	Intermediate Similarity	NPC125290
0.7778	Intermediate Similarity	NPC281296
0.775	Intermediate Similarity	NPC199445
0.7717	Intermediate Similarity	NPC107243
0.7692	Intermediate Similarity	NPC54905
0.7692	Intermediate Similarity	NPC476488
0.7692	Intermediate Similarity	NPC314009
0.7692	Intermediate Similarity	NPC476487
0.7683	Intermediate Similarity	NPC218817
0.7683	Intermediate Similarity	NPC11796
0.7683	Intermediate Similarity	NPC127526
0.7683	Intermediate Similarity	NPC121200
0.7625	Intermediate Similarity	NPC227396
0.7619	Intermediate Similarity	NPC191711
0.7619	Intermediate Similarity	NPC470241
0.7595	Intermediate Similarity	NPC126061
0.759	Intermediate Similarity	NPC55304
0.759	Intermediate Similarity	NPC226226
0.7556	Intermediate Similarity	NPC45269
0.7532	Intermediate Similarity	NPC99619
0.7532	Intermediate Similarity	NPC60120
0.7532	Intermediate Similarity	NPC26500
0.7528	Intermediate Similarity	NPC155479
0.7527	Intermediate Similarity	NPC475894
0.7527	Intermediate Similarity	NPC57416
0.75	Intermediate Similarity	NPC245947
0.75	Intermediate Similarity	NPC255863
0.75	Intermediate Similarity	NPC275098
0.75	Intermediate Similarity	NPC136164
0.75	Intermediate Similarity	NPC312215
0.75	Intermediate Similarity	NPC263347
0.7473	Intermediate Similarity	NPC243866
0.7471	Intermediate Similarity	NPC261380
0.7468	Intermediate Similarity	NPC318766
0.7468	Intermediate Similarity	NPC42526
0.7444	Intermediate Similarity	NPC46281
0.7444	Intermediate Similarity	NPC145666
0.7442	Intermediate Similarity	NPC69469
0.7439	Intermediate Similarity	NPC469514
0.7439	Intermediate Similarity	NPC469646
0.7436	Intermediate Similarity	NPC319007
0.7436	Intermediate Similarity	NPC224532
0.7419	Intermediate Similarity	NPC155676
0.7416	Intermediate Similarity	NPC48866
0.7416	Intermediate Similarity	NPC294480
0.7416	Intermediate Similarity	NPC247406
0.7391	Intermediate Similarity	NPC7165
0.7386	Intermediate Similarity	NPC212843
0.7381	Intermediate Similarity	NPC472013
0.7381	Intermediate Similarity	NPC476624
0.7381	Intermediate Similarity	NPC89128
0.7368	Intermediate Similarity	NPC470320
0.7363	Intermediate Similarity	NPC154101
0.7356	Intermediate Similarity	NPC158756
0.7356	Intermediate Similarity	NPC165064
0.7349	Intermediate Similarity	NPC116177
0.7349	Intermediate Similarity	NPC320630
0.7349	Intermediate Similarity	NPC476439
0.7349	Intermediate Similarity	NPC7563
0.7342	Intermediate Similarity	NPC236208
0.7342	Intermediate Similarity	NPC143396
0.7342	Intermediate Similarity	NPC470436
0.734	Intermediate Similarity	NPC477949
0.7333	Intermediate Similarity	NPC214387
0.7333	Intermediate Similarity	NPC2983
0.7333	Intermediate Similarity	NPC477215
0.7333	Intermediate Similarity	NPC476388
0.7333	Intermediate Similarity	NPC54689
0.7333	Intermediate Similarity	NPC310236
0.7333	Intermediate Similarity	NPC472970
0.7333	Intermediate Similarity	NPC170775
0.7333	Intermediate Similarity	NPC472971
0.7326	Intermediate Similarity	NPC85772
0.7312	Intermediate Similarity	NPC472469
0.7303	Intermediate Similarity	NPC477959
0.7303	Intermediate Similarity	NPC237540
0.7303	Intermediate Similarity	NPC96496
0.7303	Intermediate Similarity	NPC86005
0.7292	Intermediate Similarity	NPC477950
0.7292	Intermediate Similarity	NPC282524
0.7284	Intermediate Similarity	NPC238425
0.7284	Intermediate Similarity	NPC472018
0.7284	Intermediate Similarity	NPC474543
0.7283	Intermediate Similarity	NPC66429
0.7283	Intermediate Similarity	NPC152897
0.7273	Intermediate Similarity	NPC318420
0.7273	Intermediate Similarity	NPC470755
0.7273	Intermediate Similarity	NPC28887
0.7273	Intermediate Similarity	NPC326268
0.7263	Intermediate Similarity	NPC235464
0.7263	Intermediate Similarity	NPC48647
0.7263	Intermediate Similarity	NPC197386
0.7263	Intermediate Similarity	NPC166745
0.7262	Intermediate Similarity	NPC93763
0.7262	Intermediate Similarity	NPC267231
0.7262	Intermediate Similarity	NPC108816
0.7262	Intermediate Similarity	NPC478122
0.7262	Intermediate Similarity	NPC476627
0.7253	Intermediate Similarity	NPC123854
0.7253	Intermediate Similarity	NPC320026
0.7253	Intermediate Similarity	NPC477149
0.7253	Intermediate Similarity	NPC477147
0.725	Intermediate Similarity	NPC4299
0.725	Intermediate Similarity	NPC472017
0.7241	Intermediate Similarity	NPC16488
0.7241	Intermediate Similarity	NPC477784
0.7241	Intermediate Similarity	NPC477785
0.7241	Intermediate Similarity	NPC62214
0.7241	Intermediate Similarity	NPC477786
0.7234	Intermediate Similarity	NPC301534
0.7234	Intermediate Similarity	NPC29152
0.7234	Intermediate Similarity	NPC250757
0.7229	Intermediate Similarity	NPC474447
0.7222	Intermediate Similarity	NPC193843
0.7222	Intermediate Similarity	NPC476803
0.7222	Intermediate Similarity	NPC476805
0.7222	Intermediate Similarity	NPC183546
0.7222	Intermediate Similarity	NPC249889
0.7216	Intermediate Similarity	NPC118405
0.7216	Intermediate Similarity	NPC195290
0.7216	Intermediate Similarity	NPC204450
0.7215	Intermediate Similarity	NPC476614
0.7209	Intermediate Similarity	NPC52861
0.7209	Intermediate Similarity	NPC472471
0.7204	Intermediate Similarity	NPC53685
0.7204	Intermediate Similarity	NPC65829
0.72	Intermediate Similarity	NPC243532
0.72	Intermediate Similarity	NPC327112
0.7195	Intermediate Similarity	NPC474551
0.7195	Intermediate Similarity	NPC472966
0.7191	Intermediate Similarity	NPC315395
0.7191	Intermediate Similarity	NPC476982
0.7191	Intermediate Similarity	NPC469910
0.7191	Intermediate Similarity	NPC469483
0.7191	Intermediate Similarity	NPC469994
0.7191	Intermediate Similarity	NPC261721
0.7191	Intermediate Similarity	NPC316426
0.7188	Intermediate Similarity	NPC218383
0.7188	Intermediate Similarity	NPC477521
0.7179	Intermediate Similarity	NPC154728
0.7179	Intermediate Similarity	NPC304665
0.7179	Intermediate Similarity	NPC126899
0.7176	Intermediate Similarity	NPC82488
0.7176	Intermediate Similarity	NPC7232
0.7176	Intermediate Similarity	NPC308545
0.7174	Intermediate Similarity	NPC300312
0.7174	Intermediate Similarity	NPC111114
0.7174	Intermediate Similarity	NPC261607
0.7172	Intermediate Similarity	NPC321670
0.7159	Intermediate Similarity	NPC96259
0.7159	Intermediate Similarity	NPC141193
0.7159	Intermediate Similarity	NPC476804
0.7159	Intermediate Similarity	NPC475732
0.7159	Intermediate Similarity	NPC295799
0.7158	Intermediate Similarity	NPC469432
0.7158	Intermediate Similarity	NPC53844
0.7158	Intermediate Similarity	NPC475438
0.7158	Intermediate Similarity	NPC156546
0.7143	Intermediate Similarity	NPC471061
0.7143	Intermediate Similarity	NPC232747
0.7143	Intermediate Similarity	NPC226592
0.7143	Intermediate Similarity	NPC276769
0.7143	Intermediate Similarity	NPC236390
0.7143	Intermediate Similarity	NPC475050
0.7129	Intermediate Similarity	NPC474901
0.7129	Intermediate Similarity	NPC475941
0.7128	Intermediate Similarity	NPC469599
0.7128	Intermediate Similarity	NPC476174
0.7128	Intermediate Similarity	NPC20546
0.7128	Intermediate Similarity	NPC88310
0.7126	Intermediate Similarity	NPC133844
0.7126	Intermediate Similarity	NPC26624
0.7126	Intermediate Similarity	NPC20262
0.7126	Intermediate Similarity	NPC474252
0.7126	Intermediate Similarity	NPC89555
0.7126	Intermediate Similarity	NPC256750
0.7125	Intermediate Similarity	NPC101622
0.7125	Intermediate Similarity	NPC469677
0.7113	Intermediate Similarity	NPC476223
0.7113	Intermediate Similarity	NPC224720
0.7113	Intermediate Similarity	NPC476240
0.7113	Intermediate Similarity	NPC472924
0.7111	Intermediate Similarity	NPC179659
0.7111	Intermediate Similarity	NPC471738
0.7111	Intermediate Similarity	NPC475405

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 NPC201225 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	1822
0.2-0.3	4049
0.3-0.4	2167
0.4-0.5	542
0.5-0.6	320
0.6-0.7	86
0.7-0.8	10
0.8-0.85	6
0.85-0.9	7
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD4270	Approved
0.9605	High Similarity	NPD4269	Approved
0.96	High Similarity	NPD4252	Approved
0.9241	High Similarity	NPD5363	Approved
0.9125	High Similarity	NPD5786	Approved
0.8974	High Similarity	NPD5369	Approved
0.8831	High Similarity	NPD4271	Approved
0.8831	High Similarity	NPD4268	Approved
0.869	High Similarity	NPD5785	Approved
0.8608	High Similarity	NPD4822	Approved
0.8608	High Similarity	NPD4821	Approved
0.8608	High Similarity	NPD5790	Clinical (unspecified phase)
0.8608	High Similarity	NPD4819	Approved
0.8608	High Similarity	NPD4820	Approved
0.859	High Similarity	NPD5784	Clinical (unspecified phase)
0.8519	High Similarity	NPD5362	Discontinued
0.8375	Intermediate Similarity	NPD5368	Approved
0.8293	Intermediate Similarity	NPD5332	Approved
0.8293	Intermediate Similarity	NPD5331	Approved
0.8272	Intermediate Similarity	NPD4790	Discontinued
0.8171	Intermediate Similarity	NPD6435	Approved
0.814	Intermediate Similarity	NPD5370	Suspended
0.7955	Intermediate Similarity	NPD4810	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4251	Approved
0.7907	Intermediate Similarity	NPD4250	Approved
0.7857	Intermediate Similarity	NPD7154	Phase 3
0.7791	Intermediate Similarity	NPD4249	Approved
0.7674	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7637	Suspended
0.7159	Intermediate Similarity	NPD5766	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD5779	Approved
0.7067	Intermediate Similarity	NPD3198	Approved
0.6989	Remote Similarity	NPD7983	Approved
0.6932	Remote Similarity	NPD5209	Approved
0.6923	Remote Similarity	NPD3197	Phase 1
0.6875	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3665	Phase 1
0.6778	Remote Similarity	NPD3133	Approved
0.6778	Remote Similarity	NPD3666	Approved
0.6774	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6101	Approved
0.6771	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6399	Phase 3
0.6731	Remote Similarity	NPD6371	Approved
0.6701	Remote Similarity	NPD7839	Suspended
0.6701	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6084	Phase 2
0.6633	Remote Similarity	NPD6083	Phase 2
0.6632	Remote Similarity	NPD5284	Approved
0.6632	Remote Similarity	NPD6411	Approved
0.6632	Remote Similarity	NPD5281	Approved
0.663	Remote Similarity	NPD6684	Approved
0.663	Remote Similarity	NPD5330	Approved
0.663	Remote Similarity	NPD6409	Approved
0.663	Remote Similarity	NPD7334	Approved
0.663	Remote Similarity	NPD7146	Approved
0.663	Remote Similarity	NPD7521	Approved
0.6622	Remote Similarity	NPD3194	Approved
0.6622	Remote Similarity	NPD4266	Approved
0.6622	Remote Similarity	NPD3196	Approved
0.6622	Remote Similarity	NPD3195	Phase 2
0.6602	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4786	Approved
0.6571	Remote Similarity	NPD6420	Discontinued
0.6566	Remote Similarity	NPD7638	Approved
0.6556	Remote Similarity	NPD3667	Approved
0.6514	Remote Similarity	NPD7115	Discovery
0.6489	Remote Similarity	NPD6903	Approved
0.6489	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3172	Approved
0.6477	Remote Similarity	NPD4802	Phase 2
0.6477	Remote Similarity	NPD3732	Approved
0.6477	Remote Similarity	NPD4238	Approved
0.6452	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD5210	Approved
0.6429	Remote Similarity	NPD4629	Approved
0.6421	Remote Similarity	NPD4753	Phase 2
0.64	Remote Similarity	NPD5696	Approved
0.64	Remote Similarity	NPD4225	Approved
0.6381	Remote Similarity	NPD6899	Approved
0.6381	Remote Similarity	NPD6881	Approved
0.6373	Remote Similarity	NPD5211	Phase 2
0.6355	Remote Similarity	NPD6649	Approved
0.6355	Remote Similarity	NPD6650	Approved
0.6354	Remote Similarity	NPD6698	Approved
0.6354	Remote Similarity	NPD46	Approved
0.6346	Remote Similarity	NPD6402	Approved
0.6346	Remote Similarity	NPD7128	Approved
0.6346	Remote Similarity	NPD6675	Approved
0.6346	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6373	Approved
0.6321	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6647	Phase 2
0.6304	Remote Similarity	NPD6110	Phase 1
0.6289	Remote Similarity	NPD7515	Phase 2
0.6289	Remote Similarity	NPD6079	Approved
0.6286	Remote Similarity	NPD5697	Approved
0.6277	Remote Similarity	NPD5279	Phase 3
0.6277	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7102	Approved
0.6262	Remote Similarity	NPD6883	Approved
0.6262	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD5328	Approved
0.6226	Remote Similarity	NPD7320	Approved
0.6226	Remote Similarity	NPD6011	Approved
0.6224	Remote Similarity	NPD4202	Approved
0.6216	Remote Similarity	NPD29	Approved
0.6216	Remote Similarity	NPD28	Approved
0.6204	Remote Similarity	NPD6869	Approved
0.6204	Remote Similarity	NPD6847	Approved
0.6204	Remote Similarity	NPD6617	Approved
0.6204	Remote Similarity	NPD8130	Phase 1
0.6196	Remote Similarity	NPD4221	Approved
0.6196	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4223	Phase 3
0.618	Remote Similarity	NPD4756	Discovery
0.6176	Remote Similarity	NPD5285	Approved
0.6176	Remote Similarity	NPD4696	Approved
0.6176	Remote Similarity	NPD5286	Approved
0.617	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1694	Approved
0.617	Remote Similarity	NPD5329	Approved
0.6168	Remote Similarity	NPD6013	Approved
0.6168	Remote Similarity	NPD6413	Approved
0.6168	Remote Similarity	NPD6014	Approved
0.6168	Remote Similarity	NPD6012	Approved
0.6164	Remote Similarity	NPD3173	Approved
0.6162	Remote Similarity	NPD5282	Discontinued
0.6154	Remote Similarity	NPD5765	Approved
0.6154	Remote Similarity	NPD7514	Phase 3
0.6147	Remote Similarity	NPD8297	Approved
0.6147	Remote Similarity	NPD6882	Approved
0.6147	Remote Similarity	NPD6053	Discontinued
0.6146	Remote Similarity	NPD6672	Approved
0.6146	Remote Similarity	NPD5737	Approved
0.6145	Remote Similarity	NPD7331	Phase 2
0.6139	Remote Similarity	NPD4755	Approved
0.6136	Remote Similarity	NPD8039	Approved
0.6134	Remote Similarity	NPD6085	Phase 2
0.6134	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5701	Approved
0.6132	Remote Similarity	NPD6685	Approved
0.6129	Remote Similarity	NPD4788	Approved
0.6117	Remote Similarity	NPD5223	Approved
0.6111	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7145	Approved
0.6105	Remote Similarity	NPD5690	Phase 2
0.6105	Remote Similarity	NPD6098	Approved
0.61	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6902	Approved
0.6082	Remote Similarity	NPD6051	Approved
0.6082	Remote Similarity	NPD6904	Approved
0.6082	Remote Similarity	NPD6673	Approved
0.6082	Remote Similarity	NPD6080	Approved
0.6078	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4197	Approved
0.6064	Remote Similarity	NPD3668	Phase 3
0.6061	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7632	Discontinued
0.6058	Remote Similarity	NPD5225	Approved
0.6058	Remote Similarity	NPD5226	Approved
0.6058	Remote Similarity	NPD4633	Approved
0.6058	Remote Similarity	NPD5224	Approved
0.6055	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD368	Approved
0.6047	Remote Similarity	NPD7143	Approved
0.6047	Remote Similarity	NPD7144	Approved
0.6044	Remote Similarity	NPD6929	Approved
0.604	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4697	Phase 3
0.604	Remote Similarity	NPD5221	Approved
0.604	Remote Similarity	NPD5222	Approved
0.6023	Remote Similarity	NPD6924	Approved
0.6023	Remote Similarity	NPD6926	Approved
0.6022	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7838	Discovery
0.602	Remote Similarity	NPD5207	Approved
0.6019	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD6925	Approved
0.6	Remote Similarity	NPD7748	Approved
0.5981	Remote Similarity	NPD6412	Phase 2
0.598	Remote Similarity	NPD7902	Approved
0.598	Remote Similarity	NPD5173	Approved
0.5979	Remote Similarity	NPD4518	Approved
0.5978	Remote Similarity	NPD6931	Approved
0.5978	Remote Similarity	NPD7332	Phase 2
0.5978	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD6930	Phase 2
0.5977	Remote Similarity	NPD7150	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