NPASS Compound

Structure

NPC474209 OpenBabel07101719522D 27 30 0 0 1 0 0 0 0 0999 V2000 -3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -3.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -1.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0981 -2.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0981 1.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 26 1 0 0 0 0 5 7 1 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 9 15 1 0 0 0 0 9 16 2 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 20 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 12 27 1 0 0 0 0 13 21 1 6 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 23 2 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 20 1 6 0 0 0 17 21 1 0 0 0 0 18 24 1 0 0 0 0 19 25 2 0 0 0 0 20 2 1 1 0 0 0 21 3 1 6 0 0 0 22 8 1 6 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	388.248
LogP:	3.023
LogD:	2.752
LogS:	-4.288
# Rotatable Bonds:	3
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	5.132
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.009
MDCK Permeability:	2.6646173864719458e-05
Pgp-inhibitor:	0.8
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	94.338623046875%
Volume Distribution (VD):	0.673
Pgp-substrate:	2.3902063369750977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.221
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.763
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	2.586
Half-life (T1/2):	0.444

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.77
Drug-inuced Liver Injury (DILI):	0.195
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.789
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.928
Carcinogencity:	0.65
Eye Corrosion:	0.005
Eye Irritation:	0.024
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC474209

Natural Product ID:	NPC474209
*Common Name:**	2-Hydroxy-5-Methoxy-3-(((2R,4Ar,5R,6S,8As)-5,6,8A-Trimethyloctahydro-1H-Spiro[Naphthalene-2,2'-Oxirane]-5-Yl)Methyl)Cyclohexa-2,5-Diene-1,4-Dione
IUPAC Name:	3-[[(1R,2S,4aS,6R,8aR)-1,2,4a-trimethylspiro[3,4,5,7,8,8a-hexahydro-2H-naphthalene-6,2'-oxirane]-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	5-epi-ilimaquinone epoxide
Standard InCHIKey:	GADBSBRCTMKTAH-XAYDSTPHSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-13-5-7-20(2)11-22(12-27-22)8-6-17(20)21(13,3)10-14-18(24)15(23)9-16(26-4)19(14)25/h9,13,17,24H,5-8,10-12H2,1-4H3/t13-,17+,20-,21+,22+/m0/s1
SMILES:	CC1CCC2(CC3(CCC2C1(C)CC4=C(C(=O)C=C(C4=O)OC)O)CO3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463503
PubChem CID:	44566659
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002802] Prenylquinones

*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
NPO4760	Polyfibrospongia australis	n.a.	n.a.	n.a.	n.a.	Taiwan	n.a.	PMID[9051909]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.6	ug.mL-1	PMID[553146]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1.2	ug.mL-1	PMID[553146]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.1	ug.mL-1	PMID[553146]

☑ 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 NPC474209 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	209
0.1-0.2	1363
0.2-0.3	5008
0.3-0.4	12598
0.4-0.5	11330
0.5-0.6	6918
0.6-0.7	4325
0.7-0.8	903
0.8-0.85	30
0.85-0.9	11
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475823
0.9176	High Similarity	NPC6185
0.9176	High Similarity	NPC241512
0.8953	High Similarity	NPC132228
0.8953	High Similarity	NPC8518
0.8953	High Similarity	NPC263997
0.8778	High Similarity	NPC26865
0.8736	High Similarity	NPC474680
0.8571	High Similarity	NPC476808
0.8523	High Similarity	NPC133652
0.8506	High Similarity	NPC105803
0.8488	Intermediate Similarity	NPC474085
0.8488	Intermediate Similarity	NPC55869
0.8462	Intermediate Similarity	NPC223093
0.8454	Intermediate Similarity	NPC131366
0.8454	Intermediate Similarity	NPC179208
0.8391	Intermediate Similarity	NPC103486
0.8387	Intermediate Similarity	NPC23170
0.8372	Intermediate Similarity	NPC108955
0.8372	Intermediate Similarity	NPC476809
0.837	Intermediate Similarity	NPC248913
0.8352	Intermediate Similarity	NPC68148
0.8352	Intermediate Similarity	NPC65615
0.8276	Intermediate Similarity	NPC99308
0.8261	Intermediate Similarity	NPC38952
0.8256	Intermediate Similarity	NPC476177
0.8222	Intermediate Similarity	NPC94666
0.8191	Intermediate Similarity	NPC474328
0.8191	Intermediate Similarity	NPC212812
0.8161	Intermediate Similarity	NPC2482
0.8161	Intermediate Similarity	NPC469637
0.814	Intermediate Similarity	NPC30321
0.8118	Intermediate Similarity	NPC92080
0.8085	Intermediate Similarity	NPC211230
0.8068	Intermediate Similarity	NPC473217
0.8068	Intermediate Similarity	NPC121984
0.8046	Intermediate Similarity	NPC192329
0.8046	Intermediate Similarity	NPC475681
0.8043	Intermediate Similarity	NPC53454
0.8043	Intermediate Similarity	NPC475001
0.8043	Intermediate Similarity	NPC185059
0.8043	Intermediate Similarity	NPC230387
0.8023	Intermediate Similarity	NPC476811
0.8022	Intermediate Similarity	NPC203795
0.8021	Intermediate Similarity	NPC272411
0.8	Intermediate Similarity	NPC196485
0.8	Intermediate Similarity	NPC237712
0.8	Intermediate Similarity	NPC245972
0.8	Intermediate Similarity	NPC40170
0.7979	Intermediate Similarity	NPC174167
0.7979	Intermediate Similarity	NPC185936
0.7979	Intermediate Similarity	NPC470036
0.7979	Intermediate Similarity	NPC99380
0.7979	Intermediate Similarity	NPC168027
0.7978	Intermediate Similarity	NPC48362
0.7959	Intermediate Similarity	NPC472972
0.7957	Intermediate Similarity	NPC310010
0.7957	Intermediate Similarity	NPC474245
0.7957	Intermediate Similarity	NPC326627
0.7957	Intermediate Similarity	NPC119416
0.7938	Intermediate Similarity	NPC471916
0.7938	Intermediate Similarity	NPC170131
0.7917	Intermediate Similarity	NPC280725
0.7917	Intermediate Similarity	NPC147232
0.7917	Intermediate Similarity	NPC474602
0.7912	Intermediate Similarity	NPC32037
0.7912	Intermediate Similarity	NPC469993
0.7907	Intermediate Similarity	NPC26504
0.7895	Intermediate Similarity	NPC263780
0.7895	Intermediate Similarity	NPC12722
0.7889	Intermediate Similarity	NPC53733
0.7882	Intermediate Similarity	NPC147438
0.7865	Intermediate Similarity	NPC225515
0.7865	Intermediate Similarity	NPC116797
0.7865	Intermediate Similarity	NPC278459
0.7864	Intermediate Similarity	NPC87335
0.7849	Intermediate Similarity	NPC206060
0.7849	Intermediate Similarity	NPC474677
0.7849	Intermediate Similarity	NPC307298
0.7849	Intermediate Similarity	NPC48107
0.7841	Intermediate Similarity	NPC170394
0.7841	Intermediate Similarity	NPC27817
0.7835	Intermediate Similarity	NPC94337
0.7826	Intermediate Similarity	NPC145879
0.7826	Intermediate Similarity	NPC73038
0.7826	Intermediate Similarity	NPC327115
0.7826	Intermediate Similarity	NPC20688
0.7826	Intermediate Similarity	NPC472974
0.7826	Intermediate Similarity	NPC474732
0.7826	Intermediate Similarity	NPC474778
0.7826	Intermediate Similarity	NPC179591
0.7826	Intermediate Similarity	NPC474733
0.7826	Intermediate Similarity	NPC51014
0.7826	Intermediate Similarity	NPC31564
0.7816	Intermediate Similarity	NPC257666
0.7816	Intermediate Similarity	NPC266193
0.7812	Intermediate Similarity	NPC293086
0.7812	Intermediate Similarity	NPC160413
0.7812	Intermediate Similarity	NPC477439
0.7812	Intermediate Similarity	NPC472976
0.7812	Intermediate Similarity	NPC474882
0.7812	Intermediate Similarity	NPC472977
0.7802	Intermediate Similarity	NPC476412
0.7802	Intermediate Similarity	NPC144258
0.7789	Intermediate Similarity	NPC472978
0.7789	Intermediate Similarity	NPC472975
0.7778	Intermediate Similarity	NPC151519
0.7778	Intermediate Similarity	NPC144956
0.7778	Intermediate Similarity	NPC46761
0.7766	Intermediate Similarity	NPC36668
0.7766	Intermediate Similarity	NPC472475
0.7766	Intermediate Similarity	NPC112454
0.7766	Intermediate Similarity	NPC477973
0.7766	Intermediate Similarity	NPC76879
0.7766	Intermediate Similarity	NPC475108
0.7766	Intermediate Similarity	NPC472973
0.7766	Intermediate Similarity	NPC472477
0.7766	Intermediate Similarity	NPC1015
0.7766	Intermediate Similarity	NPC118011
0.7766	Intermediate Similarity	NPC31985
0.7755	Intermediate Similarity	NPC18509
0.7755	Intermediate Similarity	NPC473456
0.7753	Intermediate Similarity	NPC472478
0.7753	Intermediate Similarity	NPC18955
0.7742	Intermediate Similarity	NPC475740
0.7742	Intermediate Similarity	NPC220930
0.7742	Intermediate Similarity	NPC58063
0.7742	Intermediate Similarity	NPC471792
0.7742	Intermediate Similarity	NPC272039
0.7736	Intermediate Similarity	NPC159333
0.7732	Intermediate Similarity	NPC473170
0.7732	Intermediate Similarity	NPC477438
0.7732	Intermediate Similarity	NPC477437
0.7732	Intermediate Similarity	NPC777
0.7727	Intermediate Similarity	NPC207772
0.7727	Intermediate Similarity	NPC189485
0.7727	Intermediate Similarity	NPC80088
0.7727	Intermediate Similarity	NPC23778
0.7727	Intermediate Similarity	NPC253561
0.7717	Intermediate Similarity	NPC255174
0.7717	Intermediate Similarity	NPC79573
0.7717	Intermediate Similarity	NPC470574
0.7717	Intermediate Similarity	NPC469948
0.7717	Intermediate Similarity	NPC33663
0.7717	Intermediate Similarity	NPC197823
0.7717	Intermediate Similarity	NPC90287
0.7708	Intermediate Similarity	NPC272075
0.7708	Intermediate Similarity	NPC214756
0.7708	Intermediate Similarity	NPC233118
0.7708	Intermediate Similarity	NPC477435
0.7708	Intermediate Similarity	NPC109305
0.7708	Intermediate Similarity	NPC477436
0.7708	Intermediate Similarity	NPC295643
0.7701	Intermediate Similarity	NPC76966
0.7701	Intermediate Similarity	NPC470525
0.7701	Intermediate Similarity	NPC1254
0.7701	Intermediate Similarity	NPC186554
0.77	Intermediate Similarity	NPC207885
0.77	Intermediate Similarity	NPC112613
0.7692	Intermediate Similarity	NPC8091
0.7692	Intermediate Similarity	NPC297398
0.7692	Intermediate Similarity	NPC64600
0.7684	Intermediate Similarity	NPC113393
0.7684	Intermediate Similarity	NPC472476
0.7684	Intermediate Similarity	NPC212369
0.7684	Intermediate Similarity	NPC85173
0.7684	Intermediate Similarity	NPC472325
0.7684	Intermediate Similarity	NPC46441
0.7677	Intermediate Similarity	NPC478056
0.767	Intermediate Similarity	NPC44063
0.7667	Intermediate Similarity	NPC119229
0.7667	Intermediate Similarity	NPC90055
0.7667	Intermediate Similarity	NPC14151
0.766	Intermediate Similarity	NPC58271
0.766	Intermediate Similarity	NPC471722
0.766	Intermediate Similarity	NPC328539
0.766	Intermediate Similarity	NPC158778
0.766	Intermediate Similarity	NPC471793
0.766	Intermediate Similarity	NPC473229
0.766	Intermediate Similarity	NPC472802
0.766	Intermediate Similarity	NPC471791
0.7653	Intermediate Similarity	NPC157113
0.7653	Intermediate Similarity	NPC62516
0.7653	Intermediate Similarity	NPC192428
0.7647	Intermediate Similarity	NPC72255
0.7647	Intermediate Similarity	NPC137657
0.7647	Intermediate Similarity	NPC213366
0.7642	Intermediate Similarity	NPC90769
0.764	Intermediate Similarity	NPC283789
0.764	Intermediate Similarity	NPC474113
0.7634	Intermediate Similarity	NPC472479
0.7634	Intermediate Similarity	NPC158393
0.7634	Intermediate Similarity	NPC472985
0.7634	Intermediate Similarity	NPC472986
0.7629	Intermediate Similarity	NPC74751
0.7629	Intermediate Similarity	NPC8993
0.7624	Intermediate Similarity	NPC478176
0.7614	Intermediate Similarity	NPC165711
0.7614	Intermediate Similarity	NPC197659
0.7614	Intermediate Similarity	NPC283087

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 NPC474209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1703
0.2-0.3	3910
0.3-0.4	2300
0.4-0.5	668
0.5-0.6	158
0.6-0.7	135
0.7-0.8	96
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD4695	Discontinued
0.7957	Intermediate Similarity	NPD4753	Phase 2
0.7931	Intermediate Similarity	NPD3617	Approved
0.7835	Intermediate Similarity	NPD5221	Approved
0.7835	Intermediate Similarity	NPD5222	Approved
0.7835	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3618	Phase 1
0.7826	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD4197	Approved
0.7778	Intermediate Similarity	NPD5285	Approved
0.7778	Intermediate Similarity	NPD4696	Approved
0.7778	Intermediate Similarity	NPD5286	Approved
0.7778	Intermediate Similarity	NPD3667	Approved
0.7766	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6083	Phase 2
0.7755	Intermediate Similarity	NPD6084	Phase 2
0.7755	Intermediate Similarity	NPD5173	Approved
0.7755	Intermediate Similarity	NPD4755	Approved
0.7732	Intermediate Similarity	NPD4629	Approved
0.7732	Intermediate Similarity	NPD5695	Phase 3
0.7732	Intermediate Similarity	NPD5210	Approved
0.7717	Intermediate Similarity	NPD5329	Approved
0.77	Intermediate Similarity	NPD5223	Approved
0.7677	Intermediate Similarity	NPD5696	Approved
0.767	Intermediate Similarity	NPD5697	Approved
0.766	Intermediate Similarity	NPD5737	Approved
0.766	Intermediate Similarity	NPD6672	Approved
0.7653	Intermediate Similarity	NPD4697	Phase 3
0.7634	Intermediate Similarity	NPD5690	Phase 2
0.7629	Intermediate Similarity	NPD7748	Approved
0.7624	Intermediate Similarity	NPD5211	Phase 2
0.7624	Intermediate Similarity	NPD4633	Approved
0.7624	Intermediate Similarity	NPD5224	Approved
0.7624	Intermediate Similarity	NPD5226	Approved
0.7624	Intermediate Similarity	NPD5225	Approved
0.7609	Intermediate Similarity	NPD3133	Approved
0.7609	Intermediate Similarity	NPD4786	Approved
0.7609	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD3666	Approved
0.7604	Intermediate Similarity	NPD6079	Approved
0.7604	Intermediate Similarity	NPD7515	Phase 2
0.76	Intermediate Similarity	NPD4700	Approved
0.7596	Intermediate Similarity	NPD6881	Approved
0.7596	Intermediate Similarity	NPD6011	Approved
0.7596	Intermediate Similarity	NPD6899	Approved
0.7582	Intermediate Similarity	NPD4223	Phase 3
0.7582	Intermediate Similarity	NPD4221	Approved
0.7579	Intermediate Similarity	NPD5328	Approved
0.7573	Intermediate Similarity	NPD5739	Approved
0.7573	Intermediate Similarity	NPD7128	Approved
0.7573	Intermediate Similarity	NPD6675	Approved
0.7573	Intermediate Similarity	NPD6402	Approved
0.7549	Intermediate Similarity	NPD5174	Approved
0.7549	Intermediate Similarity	NPD5175	Approved
0.7526	Intermediate Similarity	NPD4202	Approved
0.7524	Intermediate Similarity	NPD6013	Approved
0.7524	Intermediate Similarity	NPD6012	Approved
0.7524	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD5701	Approved
0.7476	Intermediate Similarity	NPD5141	Approved
0.7453	Intermediate Similarity	NPD6883	Approved
0.7453	Intermediate Similarity	NPD7102	Approved
0.7453	Intermediate Similarity	NPD7290	Approved
0.7447	Intermediate Similarity	NPD5280	Approved
0.7447	Intermediate Similarity	NPD5279	Phase 3
0.7447	Intermediate Similarity	NPD4694	Approved
0.7429	Intermediate Similarity	NPD7320	Approved
0.7419	Intermediate Similarity	NPD3668	Phase 3
0.74	Intermediate Similarity	NPD7902	Approved
0.7396	Intermediate Similarity	NPD6904	Approved
0.7396	Intermediate Similarity	NPD6080	Approved
0.7396	Intermediate Similarity	NPD6673	Approved
0.7383	Intermediate Similarity	NPD8130	Phase 1
0.7383	Intermediate Similarity	NPD6617	Approved
0.7383	Intermediate Similarity	NPD6847	Approved
0.7383	Intermediate Similarity	NPD6869	Approved
0.7383	Intermediate Similarity	NPD6650	Approved
0.7383	Intermediate Similarity	NPD6649	Approved
0.7379	Intermediate Similarity	NPD4754	Approved
0.7368	Intermediate Similarity	NPD3573	Approved
0.7358	Intermediate Similarity	NPD6372	Approved
0.7358	Intermediate Similarity	NPD6373	Approved
0.7347	Intermediate Similarity	NPD6399	Phase 3
0.734	Intermediate Similarity	NPD1696	Phase 3
0.7315	Intermediate Similarity	NPD8297	Approved
0.7315	Intermediate Similarity	NPD6882	Approved
0.7264	Intermediate Similarity	NPD4729	Approved
0.7264	Intermediate Similarity	NPD4730	Approved
0.7264	Intermediate Similarity	NPD5128	Approved
0.7263	Intermediate Similarity	NPD4623	Approved
0.7263	Intermediate Similarity	NPD4689	Approved
0.7263	Intermediate Similarity	NPD5205	Approved
0.7263	Intermediate Similarity	NPD4138	Approved
0.7263	Intermediate Similarity	NPD4688	Approved
0.7263	Intermediate Similarity	NPD4693	Phase 3
0.7263	Intermediate Similarity	NPD4690	Approved
0.7263	Intermediate Similarity	NPD4519	Discontinued
0.7245	Intermediate Similarity	NPD5693	Phase 1
0.7238	Intermediate Similarity	NPD4767	Approved
0.7238	Intermediate Similarity	NPD4768	Approved
0.7222	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5133	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD4634	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5169	Approved
0.713	Intermediate Similarity	NPD5248	Approved
0.713	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5135	Approved
0.7128	Intermediate Similarity	NPD4788	Approved
0.7117	Intermediate Similarity	NPD6274	Approved
0.7103	Intermediate Similarity	NPD5168	Approved
0.71	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7900	Approved
0.7091	Intermediate Similarity	NPD4632	Approved
0.7083	Intermediate Similarity	NPD5330	Approved
0.7083	Intermediate Similarity	NPD7521	Approved
0.7083	Intermediate Similarity	NPD6098	Approved
0.7083	Intermediate Similarity	NPD6684	Approved
0.7083	Intermediate Similarity	NPD7334	Approved
0.7083	Intermediate Similarity	NPD7146	Approved
0.7083	Intermediate Similarity	NPD6409	Approved
0.7075	Intermediate Similarity	NPD6008	Approved
0.7071	Intermediate Similarity	NPD5694	Approved
0.7071	Intermediate Similarity	NPD6050	Approved
0.7065	Intermediate Similarity	NPD4195	Approved
0.7064	Intermediate Similarity	NPD5216	Approved
0.7064	Intermediate Similarity	NPD5217	Approved
0.7064	Intermediate Similarity	NPD5215	Approved
0.7064	Intermediate Similarity	NPD5127	Approved
0.7059	Intermediate Similarity	NPD3704	Approved
0.7054	Intermediate Similarity	NPD7115	Discovery
0.7054	Intermediate Similarity	NPD6009	Approved
0.7054	Intermediate Similarity	NPD6317	Approved
0.703	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6314	Approved
0.6991	Remote Similarity	NPD6313	Approved
0.6991	Remote Similarity	NPD6335	Approved
0.6989	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6868	Approved
0.6952	Remote Similarity	NPD5091	Approved
0.6939	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6903	Approved
0.6932	Remote Similarity	NPD4691	Approved
0.6931	Remote Similarity	NPD5282	Discontinued
0.693	Remote Similarity	NPD7101	Approved
0.693	Remote Similarity	NPD7100	Approved
0.6905	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5281	Approved
0.69	Remote Similarity	NPD5284	Approved
0.6893	Remote Similarity	NPD5959	Approved
0.6875	Remote Similarity	NPD5167	Approved
0.687	Remote Similarity	NPD6319	Approved
0.687	Remote Similarity	NPD6054	Approved
0.6863	Remote Similarity	NPD5654	Approved
0.6842	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7604	Phase 2
0.6818	Remote Similarity	NPD4137	Phase 3
0.681	Remote Similarity	NPD5983	Phase 2
0.681	Remote Similarity	NPD6016	Approved
0.681	Remote Similarity	NPD6015	Approved
0.6796	Remote Similarity	NPD7614	Phase 1
0.6768	Remote Similarity	NPD5208	Approved
0.6765	Remote Similarity	NPD6001	Approved
0.6752	Remote Similarity	NPD6370	Approved
0.6752	Remote Similarity	NPD5988	Approved
0.6742	Remote Similarity	NPD4747	Approved
0.6739	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4692	Approved
0.6737	Remote Similarity	NPD4139	Approved
0.6727	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6059	Approved
0.6703	Remote Similarity	NPD4058	Approved
0.6702	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6639	Remote Similarity	NPD7492	Approved
0.6635	Remote Similarity	NPD7732	Phase 3
0.6634	Remote Similarity	NPD4096	Approved
0.6633	Remote Similarity	NPD1694	Approved
0.6632	Remote Similarity	NPD7525	Registered
0.663	Remote Similarity	NPD6942	Approved
0.663	Remote Similarity	NPD7339	Approved
0.6604	Remote Similarity	NPD7640	Approved
0.6604	Remote Similarity	NPD7639	Approved
0.66	Remote Similarity	NPD4518	Approved
0.6583	Remote Similarity	NPD6336	Discontinued
0.6583	Remote Similarity	NPD6616	Approved
0.6569	Remote Similarity	NPD6411	Approved
0.6552	Remote Similarity	NPD7341	Phase 2
0.6545	Remote Similarity	NPD6614	Approved
0.6545	Remote Similarity	NPD6412	Phase 2

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