NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	2.954
LogD:	2.688
LogS:	-3.053
# Rotatable Bonds:	2
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	4.143
Fsp3:	0.733
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:	-4.532
MDCK Permeability:	2.5313947844551876e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	53.42014694213867%
Volume Distribution (VD):	2.161
Pgp-substrate:	47.16352844238281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.385
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.755
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.339
CYP3A4-inhibitor:	0.33
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	6.109
Half-life (T1/2):	0.332

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.351
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.959
Carcinogencity:	0.831
Eye Corrosion:	0.988
Eye Irritation:	0.963
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC290350

Natural Product ID:	NPC290350
*Common Name:**	Epipolygodial
IUPAC Name:	(1S,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde
Synonyms:	Epipolygodial; Isopolygodial
Standard InCHIKey:	AZJUJOFIHHNCSV-VNHYZAJKSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13+,15-/m1/s1
SMILES:	CC1(C)CCC[C@]2(C)[C@H](C=O)C(=CC[C@@H]12)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL218100
PubChem CID:	667499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0003940] Organic oxides

*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
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17286431]
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24725159]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[Nippon Kogaku Zasshi, 91, (1970), 762]
NPO30896	Polygonum hydropiper	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4929	Pyropia perforata	Species	Bangiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14437	Rimularia gibbosa	Species	Trapeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22984	Aframomum sceptrum	Species	Zingiberaceae	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
MIC	15

Activity Type	# Activity
Organism	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT770	Organism	Rhizopus microsporus var. chinensis	Rhizopus microsporus var. chinensis	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT768	Organism	Sclerotinia	Sclerotinia	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT772	Organism	Pichia anomala	Wickerhamomyces anomalus	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT771	Organism	Penicillium crustosum	Penicillium crustosum	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT769	Organism	Mucor mucedo	Mucor mucedo	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT767	Organism	Pichia jadinii	Cyberlindnera jadinii	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[531425]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[531425]

☑ 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 NPC290350 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	188
0.1-0.2	2104
0.2-0.3	12097
0.3-0.4	14633
0.4-0.5	7973
0.5-0.6	4252
0.6-0.7	1234
0.7-0.8	187
0.8-0.85	18
0.85-0.9	5
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC4370
0.9394	High Similarity	NPC474562
0.9231	High Similarity	NPC155198
0.9118	High Similarity	NPC211641
0.9118	High Similarity	NPC128346
0.9118	High Similarity	NPC219232
0.8906	High Similarity	NPC52449
0.8906	High Similarity	NPC169275
0.8824	High Similarity	NPC304983
0.8611	High Similarity	NPC115515
0.8592	High Similarity	NPC19907
0.8507	High Similarity	NPC193770
0.8438	Intermediate Similarity	NPC127582
0.8382	Intermediate Similarity	NPC260474
0.8382	Intermediate Similarity	NPC188292
0.8333	Intermediate Similarity	NPC469793
0.8333	Intermediate Similarity	NPC475124
0.8333	Intermediate Similarity	NPC469796
0.8333	Intermediate Similarity	NPC285371
0.8281	Intermediate Similarity	NPC276764
0.8281	Intermediate Similarity	NPC472304
0.8243	Intermediate Similarity	NPC90965
0.8243	Intermediate Similarity	NPC170793
0.8209	Intermediate Similarity	NPC251118
0.8209	Intermediate Similarity	NPC268039
0.8182	Intermediate Similarity	NPC288253
0.8158	Intermediate Similarity	NPC470813
0.8143	Intermediate Similarity	NPC2634
0.8143	Intermediate Similarity	NPC265782
0.8143	Intermediate Similarity	NPC251929
0.8143	Intermediate Similarity	NPC260040
0.8133	Intermediate Similarity	NPC474509
0.8125	Intermediate Similarity	NPC27610
0.8125	Intermediate Similarity	NPC56905
0.8116	Intermediate Similarity	NPC310992
0.8116	Intermediate Similarity	NPC87141
0.8108	Intermediate Similarity	NPC228911
0.8065	Intermediate Similarity	NPC250539
0.8065	Intermediate Similarity	NPC100809
0.8065	Intermediate Similarity	NPC209431
0.806	Intermediate Similarity	NPC212210
0.8052	Intermediate Similarity	NPC307258
0.8028	Intermediate Similarity	NPC54123
0.8	Intermediate Similarity	NPC139397
0.8	Intermediate Similarity	NPC256846
0.7971	Intermediate Similarity	NPC475523
0.7949	Intermediate Similarity	NPC470812
0.7941	Intermediate Similarity	NPC470329
0.7917	Intermediate Similarity	NPC474228
0.7917	Intermediate Similarity	NPC144947
0.7917	Intermediate Similarity	NPC303613
0.7887	Intermediate Similarity	NPC307176
0.7867	Intermediate Similarity	NPC59436
0.7867	Intermediate Similarity	NPC80088
0.7867	Intermediate Similarity	NPC253561
0.7848	Intermediate Similarity	NPC70685
0.7848	Intermediate Similarity	NPC2709
0.7846	Intermediate Similarity	NPC311852
0.7808	Intermediate Similarity	NPC75485
0.7808	Intermediate Similarity	NPC168975
0.7808	Intermediate Similarity	NPC309852
0.7794	Intermediate Similarity	NPC469662
0.7794	Intermediate Similarity	NPC6697
0.7778	Intermediate Similarity	NPC190035
0.7761	Intermediate Similarity	NPC213152
0.7761	Intermediate Similarity	NPC60565
0.7742	Intermediate Similarity	NPC22182
0.7703	Intermediate Similarity	NPC65650
0.7703	Intermediate Similarity	NPC476346
0.7692	Intermediate Similarity	NPC115385
0.7692	Intermediate Similarity	NPC142683
0.7671	Intermediate Similarity	NPC470045
0.7671	Intermediate Similarity	NPC251705
0.7671	Intermediate Similarity	NPC109576
0.7671	Intermediate Similarity	NPC56747
0.7671	Intermediate Similarity	NPC180015
0.7671	Intermediate Similarity	NPC470044
0.7671	Intermediate Similarity	NPC130016
0.7662	Intermediate Similarity	NPC472301
0.7647	Intermediate Similarity	NPC202118
0.7647	Intermediate Similarity	NPC197238
0.7647	Intermediate Similarity	NPC165695
0.7639	Intermediate Similarity	NPC159577
0.7639	Intermediate Similarity	NPC282593
0.7639	Intermediate Similarity	NPC35734
0.7632	Intermediate Similarity	NPC62336
0.76	Intermediate Similarity	NPC69408
0.76	Intermediate Similarity	NPC470525
0.76	Intermediate Similarity	NPC263582
0.76	Intermediate Similarity	NPC1254
0.7595	Intermediate Similarity	NPC470165
0.7576	Intermediate Similarity	NPC170799
0.7576	Intermediate Similarity	NPC308108
0.7568	Intermediate Similarity	NPC474796
0.7568	Intermediate Similarity	NPC474797
0.7568	Intermediate Similarity	NPC329866
0.7568	Intermediate Similarity	NPC20025
0.7568	Intermediate Similarity	NPC255021
0.7568	Intermediate Similarity	NPC238146
0.7564	Intermediate Similarity	NPC119229
0.7564	Intermediate Similarity	NPC149237
0.7564	Intermediate Similarity	NPC90055
0.7564	Intermediate Similarity	NPC116797
0.7534	Intermediate Similarity	NPC305501
0.7534	Intermediate Similarity	NPC21944
0.7534	Intermediate Similarity	NPC225467
0.7534	Intermediate Similarity	NPC115023
0.7534	Intermediate Similarity	NPC5701
0.7534	Intermediate Similarity	NPC234707
0.7532	Intermediate Similarity	NPC283789
0.7532	Intermediate Similarity	NPC152061
0.7532	Intermediate Similarity	NPC476177
0.7531	Intermediate Similarity	NPC168248
0.75	Intermediate Similarity	NPC61702
0.75	Intermediate Similarity	NPC162867
0.75	Intermediate Similarity	NPC197659
0.75	Intermediate Similarity	NPC286814
0.75	Intermediate Similarity	NPC472300
0.747	Intermediate Similarity	NPC469546
0.747	Intermediate Similarity	NPC184663
0.7467	Intermediate Similarity	NPC293803
0.7467	Intermediate Similarity	NPC476795
0.7467	Intermediate Similarity	NPC473171
0.7436	Intermediate Similarity	NPC471514
0.7436	Intermediate Similarity	NPC472478
0.7436	Intermediate Similarity	NPC2482
0.7429	Intermediate Similarity	NPC183422
0.7424	Intermediate Similarity	NPC281986
0.7424	Intermediate Similarity	NPC192427
0.7424	Intermediate Similarity	NPC321568
0.7424	Intermediate Similarity	NPC208749
0.7424	Intermediate Similarity	NPC22019
0.7407	Intermediate Similarity	NPC33881
0.7403	Intermediate Similarity	NPC189485
0.7391	Intermediate Similarity	NPC32285
0.7385	Intermediate Similarity	NPC188789
0.7385	Intermediate Similarity	NPC200258
0.7381	Intermediate Similarity	NPC159748
0.7381	Intermediate Similarity	NPC101651
0.7375	Intermediate Similarity	NPC22611
0.7375	Intermediate Similarity	NPC118423
0.7368	Intermediate Similarity	NPC180886
0.7361	Intermediate Similarity	NPC39157
0.7361	Intermediate Similarity	NPC142754
0.7361	Intermediate Similarity	NPC296697
0.7361	Intermediate Similarity	NPC82477
0.7361	Intermediate Similarity	NPC20610
0.7349	Intermediate Similarity	NPC473229
0.7349	Intermediate Similarity	NPC206060
0.7344	Intermediate Similarity	NPC268564
0.7344	Intermediate Similarity	NPC23117
0.7342	Intermediate Similarity	NPC474085
0.7342	Intermediate Similarity	NPC99308
0.7342	Intermediate Similarity	NPC121984
0.7333	Intermediate Similarity	NPC159497
0.7324	Intermediate Similarity	NPC323005
0.7313	Intermediate Similarity	NPC60772
0.7308	Intermediate Similarity	NPC308038
0.7308	Intermediate Similarity	NPC472490
0.7308	Intermediate Similarity	NPC27817
0.7297	Intermediate Similarity	NPC133253
0.7297	Intermediate Similarity	NPC160817
0.7294	Intermediate Similarity	NPC230064
0.7294	Intermediate Similarity	NPC172101
0.7273	Intermediate Similarity	NPC266193
0.7273	Intermediate Similarity	NPC97377
0.7273	Intermediate Similarity	NPC325946
0.7273	Intermediate Similarity	NPC257666
0.7262	Intermediate Similarity	NPC472983
0.726	Intermediate Similarity	NPC182815
0.725	Intermediate Similarity	NPC186276
0.725	Intermediate Similarity	NPC103486
0.725	Intermediate Similarity	NPC268122
0.7237	Intermediate Similarity	NPC114236
0.7237	Intermediate Similarity	NPC255650
0.7231	Intermediate Similarity	NPC5626
0.7222	Intermediate Similarity	NPC20181
0.7222	Intermediate Similarity	NPC220210
0.7215	Intermediate Similarity	NPC108955
0.7215	Intermediate Similarity	NPC474956
0.7215	Intermediate Similarity	NPC476809
0.7215	Intermediate Similarity	NPC172013
0.7209	Intermediate Similarity	NPC151722
0.7206	Intermediate Similarity	NPC285594
0.7206	Intermediate Similarity	NPC96551
0.7206	Intermediate Similarity	NPC259261
0.72	Intermediate Similarity	NPC35656
0.72	Intermediate Similarity	NPC474488
0.7195	Intermediate Similarity	NPC189311
0.7195	Intermediate Similarity	NPC133652
0.7195	Intermediate Similarity	NPC476426
0.7179	Intermediate Similarity	NPC82635
0.7179	Intermediate Similarity	NPC275494
0.7179	Intermediate Similarity	NPC74410
0.7179	Intermediate Similarity	NPC469996
0.7179	Intermediate Similarity	NPC475994
0.7179	Intermediate Similarity	NPC471409
0.7179	Intermediate Similarity	NPC4827
0.7176	Intermediate Similarity	NPC191684
0.7176	Intermediate Similarity	NPC328141

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 NPC290350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	2356
0.2-0.3	4423
0.3-0.4	1576
0.4-0.5	362
0.5-0.6	192
0.6-0.7	57
0.7-0.8	7
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
0.8143	Intermediate Similarity	NPD4691	Approved
0.8	Intermediate Similarity	NPD4137	Phase 3
0.7887	Intermediate Similarity	NPD4747	Approved
0.7808	Intermediate Similarity	NPD4058	Approved
0.7576	Intermediate Similarity	NPD287	Approved
0.7568	Intermediate Similarity	NPD4687	Approved
0.7568	Intermediate Similarity	NPD5733	Approved
0.7534	Intermediate Similarity	NPD5276	Approved
0.7361	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3133	Approved
0.7073	Intermediate Similarity	NPD3666	Approved
0.7073	Intermediate Similarity	NPD3665	Phase 1
0.7037	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4695	Discontinued
0.6951	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8028	Phase 2
0.6905	Remote Similarity	NPD7521	Approved
0.6905	Remote Similarity	NPD3618	Phase 1
0.6905	Remote Similarity	NPD6684	Approved
0.6905	Remote Similarity	NPD6409	Approved
0.6905	Remote Similarity	NPD7334	Approved
0.6905	Remote Similarity	NPD5330	Approved
0.6905	Remote Similarity	NPD7146	Approved
0.6829	Remote Similarity	NPD4223	Phase 3
0.6829	Remote Similarity	NPD3667	Approved
0.6829	Remote Similarity	NPD4221	Approved
0.6778	Remote Similarity	NPD4697	Phase 3
0.6744	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6672	Approved
0.6744	Remote Similarity	NPD6903	Approved
0.6744	Remote Similarity	NPD5737	Approved
0.6706	Remote Similarity	NPD5279	Phase 3
0.6706	Remote Similarity	NPD5690	Phase 2
0.6705	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6628	Remote Similarity	NPD3573	Approved
0.6588	Remote Similarity	NPD5329	Approved
0.6588	Remote Similarity	NPD1694	Approved
0.6556	Remote Similarity	NPD7900	Approved
0.6556	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3617	Approved
0.6517	Remote Similarity	NPD7515	Phase 2
0.6512	Remote Similarity	NPD4623	Approved
0.6512	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5205	Approved
0.6512	Remote Similarity	NPD4688	Approved
0.6512	Remote Similarity	NPD4694	Approved
0.6512	Remote Similarity	NPD4690	Approved
0.6512	Remote Similarity	NPD4519	Discontinued
0.6512	Remote Similarity	NPD4138	Approved
0.6512	Remote Similarity	NPD4693	Phase 3
0.6512	Remote Similarity	NPD4689	Approved
0.6512	Remote Similarity	NPD5280	Approved
0.6484	Remote Similarity	NPD5210	Approved
0.6484	Remote Similarity	NPD4629	Approved
0.6444	Remote Similarity	NPD4202	Approved
0.6413	Remote Similarity	NPD5222	Approved
0.6413	Remote Similarity	NPD5221	Approved
0.6413	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7748	Approved
0.6364	Remote Similarity	NPD5208	Approved
0.6344	Remote Similarity	NPD7902	Approved
0.6344	Remote Similarity	NPD5173	Approved
0.6304	Remote Similarity	NPD5695	Phase 3
0.6292	Remote Similarity	NPD6673	Approved
0.6292	Remote Similarity	NPD6080	Approved
0.6292	Remote Similarity	NPD6904	Approved
0.6265	Remote Similarity	NPD4195	Approved
0.6264	Remote Similarity	NPD6399	Phase 3
0.6222	Remote Similarity	NPD5207	Approved
0.6222	Remote Similarity	NPD5692	Phase 3
0.6211	Remote Similarity	NPD5286	Approved
0.6211	Remote Similarity	NPD4696	Approved
0.6211	Remote Similarity	NPD5285	Approved
0.619	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD7331	Phase 2
0.6173	Remote Similarity	NPD8039	Approved
0.617	Remote Similarity	NPD4755	Approved
0.617	Remote Similarity	NPD6083	Phase 2
0.617	Remote Similarity	NPD6084	Phase 2
0.6163	Remote Similarity	NPD4788	Approved
0.6154	Remote Similarity	NPD6050	Approved
0.6154	Remote Similarity	NPD5281	Approved
0.6154	Remote Similarity	NPD5284	Approved
0.6154	Remote Similarity	NPD5694	Approved
0.6154	Remote Similarity	NPD5693	Phase 1
0.6146	Remote Similarity	NPD5223	Approved
0.6136	Remote Similarity	NPD6098	Approved
0.6129	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5696	Approved
0.6087	Remote Similarity	NPD7631	Approved
0.6082	Remote Similarity	NPD5225	Approved
0.6082	Remote Similarity	NPD4633	Approved
0.6082	Remote Similarity	NPD5224	Approved
0.6082	Remote Similarity	NPD5211	Phase 2
0.6082	Remote Similarity	NPD5226	Approved
0.6081	Remote Similarity	NPD4191	Approved
0.6081	Remote Similarity	NPD4193	Approved
0.6081	Remote Similarity	NPD4194	Approved
0.6081	Remote Similarity	NPD4192	Approved
0.6064	Remote Similarity	NPD7732	Phase 3
0.6044	Remote Similarity	NPD4096	Approved
0.6042	Remote Similarity	NPD4700	Approved
0.6032	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD1696	Phase 3
0.6022	Remote Similarity	NPD6001	Approved
0.602	Remote Similarity	NPD5174	Approved
0.602	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD3495	Discontinued
0.5978	Remote Similarity	NPD7609	Phase 3
0.596	Remote Similarity	NPD5141	Approved
0.593	Remote Similarity	NPD4139	Approved
0.593	Remote Similarity	NPD4692	Approved
0.5921	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5133	Approved
0.5904	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7614	Phase 1
0.5889	Remote Similarity	NPD650	Approved
0.5876	Remote Similarity	NPD6404	Discontinued
0.5859	Remote Similarity	NPD4754	Approved
0.5844	Remote Similarity	NPD7341	Phase 2
0.5842	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD4219	Approved
0.5824	Remote Similarity	NPD4518	Approved
0.5789	Remote Similarity	NPD5654	Approved
0.5784	Remote Similarity	NPD4730	Approved
0.5784	Remote Similarity	NPD6881	Approved
0.5784	Remote Similarity	NPD6899	Approved
0.5784	Remote Similarity	NPD6011	Approved
0.5784	Remote Similarity	NPD4729	Approved
0.5784	Remote Similarity	NPD5168	Approved
0.5784	Remote Similarity	NPD5128	Approved
0.5783	Remote Similarity	NPD7339	Approved
0.5783	Remote Similarity	NPD6942	Approved
0.5769	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6650	Approved
0.5769	Remote Similarity	NPD6649	Approved
0.5758	Remote Similarity	NPD5091	Approved
0.5743	Remote Similarity	NPD4767	Approved
0.5743	Remote Similarity	NPD4768	Approved
0.5743	Remote Similarity	NPD6008	Approved
0.5743	Remote Similarity	NPD5739	Approved
0.5743	Remote Similarity	NPD6675	Approved
0.5743	Remote Similarity	NPD6402	Approved
0.5743	Remote Similarity	NPD7128	Approved
0.5728	Remote Similarity	NPD6014	Approved
0.5728	Remote Similarity	NPD6013	Approved
0.5728	Remote Similarity	NPD6372	Approved
0.5728	Remote Similarity	NPD6012	Approved
0.5728	Remote Similarity	NPD6373	Approved
0.5698	Remote Similarity	NPD7645	Phase 2
0.5686	Remote Similarity	NPD5701	Approved
0.5686	Remote Similarity	NPD6412	Phase 2
0.5673	Remote Similarity	NPD5251	Approved
0.5673	Remote Similarity	NPD6883	Approved
0.5673	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5169	Approved
0.5673	Remote Similarity	NPD7290	Approved
0.5673	Remote Similarity	NPD5249	Phase 3
0.5673	Remote Similarity	NPD7102	Approved
0.5673	Remote Similarity	NPD4634	Approved
0.5673	Remote Similarity	NPD5248	Approved
0.5673	Remote Similarity	NPD5247	Approved
0.5673	Remote Similarity	NPD5135	Approved
0.5673	Remote Similarity	NPD5250	Approved
0.567	Remote Similarity	NPD5959	Approved
0.5667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6411	Approved
0.5631	Remote Similarity	NPD7320	Approved
0.5619	Remote Similarity	NPD8130	Phase 1
0.5619	Remote Similarity	NPD5216	Approved
0.5619	Remote Similarity	NPD5127	Approved
0.5619	Remote Similarity	NPD6869	Approved
0.5619	Remote Similarity	NPD6847	Approved
0.5619	Remote Similarity	NPD5215	Approved
0.5619	Remote Similarity	NPD5217	Approved
0.5619	Remote Similarity	NPD6617	Approved
0.5612	Remote Similarity	NPD7638	Approved
0.561	Remote Similarity	NPD4243	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