NPASS Compound

Structure

NPC131366 OpenBabel07101719132D 26 29 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 2 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 1 0 0 0 16 20 1 0 0 0 0 16 21 1 1 0 0 0 17 22 1 0 0 0 0 17 24 2 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 19 22 1 6 0 0 0 19 26 1 0 0 0 0 21 4 1 1 0 0 0 22 11 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.21
Volume:	379.457
LogP:	3.531
LogD:	1.532
LogS:	-2.673
# Rotatable Bonds:	3
TPSA:	63.74
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	5.082
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.783
MDCK Permeability:	2.2406509742722847e-05
Pgp-inhibitor:	0.172
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.587
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.605
Plasma Protein Binding (PPB):	58.145057678222656%
Volume Distribution (VD):	1.74
Pgp-substrate:	53.38511657714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.611
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.689
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.421
CYP3A4-inhibitor:	0.392
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	11.421
Half-life (T1/2):	0.508

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.673
Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.764
Skin Sensitization:	0.726
Carcinogencity:	0.904
Eye Corrosion:	0.952
Eye Irritation:	0.691
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC131366

Natural Product ID:	NPC131366
*Common Name:**	4'-Oxomacrophorin A
IUPAC Name:	(1S,6R)-6-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Synonyms:	4'-Oxomacrophorin A
Standard InCHIKey:	IEINAOONOAUQPK-XKRAJOFMSA-N
Standard InCHI:	InChI=1S/C22H30O4/c1-13-6-7-16-20(2,3)8-5-9-21(16,4)15(13)11-22-17(24)10-14(12-23)18(25)19(22)26-22/h10,15-16,19,23H,1,5-9,11-12H2,2-4H3/t15-,16-,19+,21+,22-/m0/s1
SMILES:	OCC1=CC(=O)[C@]2([C@@H](C1=O)O2)C[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518415
PubChem CID:	10316368
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32585	eupenicillium crustaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575965]

☑ 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	2
Others	1

Activity Type	# Activity
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.5	ug.mL-1	PMID[573611]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.25	ug.mL-1	PMID[573611]
NPT2	Others	Unspecified		Ratio IC50	=	2.0	n.a.	PMID[573611]

☑ 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 NPC131366 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	222
0.1-0.2	1301
0.2-0.3	4471
0.3-0.4	8875
0.4-0.5	13297
0.5-0.6	7258
0.6-0.7	5962
0.7-0.8	1267
0.8-0.85	31
0.85-0.9	7
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9271	High Similarity	NPC471916
0.9118	High Similarity	NPC87335
0.899	High Similarity	NPC207885
0.88	High Similarity	NPC112613
0.8776	High Similarity	NPC94337
0.8774	High Similarity	NPC159333
0.8654	High Similarity	NPC322903
0.8454	Intermediate Similarity	NPC474209
0.8454	Intermediate Similarity	NPC475823
0.8447	Intermediate Similarity	NPC95899
0.8411	Intermediate Similarity	NPC317107
0.8367	Intermediate Similarity	NPC73457
0.835	Intermediate Similarity	NPC478176
0.8333	Intermediate Similarity	NPC317687
0.8252	Intermediate Similarity	NPC470184
0.8235	Intermediate Similarity	NPC316598
0.8235	Intermediate Similarity	NPC264378
0.8229	Intermediate Similarity	NPC472986
0.8229	Intermediate Similarity	NPC472985
0.8224	Intermediate Similarity	NPC20192
0.8198	Intermediate Similarity	NPC243065
0.819	Intermediate Similarity	NPC72255
0.8182	Intermediate Similarity	NPC26865
0.8173	Intermediate Similarity	NPC39996
0.8155	Intermediate Similarity	NPC472972
0.8137	Intermediate Similarity	NPC170131
0.8125	Intermediate Similarity	NPC255174
0.8119	Intermediate Similarity	NPC476245
0.8113	Intermediate Similarity	NPC166607
0.8103	Intermediate Similarity	NPC225049
0.8095	Intermediate Similarity	NPC249187
0.8095	Intermediate Similarity	NPC247957
0.8095	Intermediate Similarity	NPC478057
0.8091	Intermediate Similarity	NPC472926
0.8073	Intermediate Similarity	NPC207689
0.8061	Intermediate Similarity	NPC53454
0.8061	Intermediate Similarity	NPC471791
0.8061	Intermediate Similarity	NPC471793
0.8058	Intermediate Similarity	NPC478056
0.8041	Intermediate Similarity	NPC470955
0.8041	Intermediate Similarity	NPC472974
0.8037	Intermediate Similarity	NPC473165
0.8037	Intermediate Similarity	NPC472925
0.802	Intermediate Similarity	NPC245972
0.802	Intermediate Similarity	NPC196227
0.802	Intermediate Similarity	NPC196485
0.802	Intermediate Similarity	NPC472976
0.802	Intermediate Similarity	NPC472977
0.8019	Intermediate Similarity	NPC160843
0.8	Intermediate Similarity	NPC472978
0.8	Intermediate Similarity	NPC47450
0.8	Intermediate Similarity	NPC172101
0.8	Intermediate Similarity	NPC116726
0.7981	Intermediate Similarity	NPC154072
0.798	Intermediate Similarity	NPC472983
0.798	Intermediate Similarity	NPC472973
0.7965	Intermediate Similarity	NPC251310
0.7959	Intermediate Similarity	NPC220930
0.7959	Intermediate Similarity	NPC272039
0.7944	Intermediate Similarity	NPC257353
0.7944	Intermediate Similarity	NPC32006
0.7944	Intermediate Similarity	NPC1679
0.7944	Intermediate Similarity	NPC85529
0.7941	Intermediate Similarity	NPC272617
0.7941	Intermediate Similarity	NPC271195
0.7938	Intermediate Similarity	NPC476426
0.7938	Intermediate Similarity	NPC6185
0.7938	Intermediate Similarity	NPC241512
0.7928	Intermediate Similarity	NPC477266
0.7928	Intermediate Similarity	NPC122056
0.7928	Intermediate Similarity	NPC472929
0.7925	Intermediate Similarity	NPC230918
0.7925	Intermediate Similarity	NPC90177
0.7921	Intermediate Similarity	NPC109305
0.7921	Intermediate Similarity	NPC476416
0.7913	Intermediate Similarity	NPC67569
0.7909	Intermediate Similarity	NPC171888
0.7909	Intermediate Similarity	NPC146945
0.7905	Intermediate Similarity	NPC81530
0.79	Intermediate Similarity	NPC38952
0.7895	Intermediate Similarity	NPC472933
0.7895	Intermediate Similarity	NPC268958
0.789	Intermediate Similarity	NPC141350
0.7876	Intermediate Similarity	NPC472934
0.7876	Intermediate Similarity	NPC477116
0.7876	Intermediate Similarity	NPC27999
0.7876	Intermediate Similarity	NPC472927
0.7864	Intermediate Similarity	NPC272411
0.7863	Intermediate Similarity	NPC470922
0.7857	Intermediate Similarity	NPC194417
0.7857	Intermediate Similarity	NPC94666
0.7857	Intermediate Similarity	NPC261330
0.7857	Intermediate Similarity	NPC238667
0.7857	Intermediate Similarity	NPC202394
0.7845	Intermediate Similarity	NPC470265
0.7845	Intermediate Similarity	NPC23786
0.7843	Intermediate Similarity	NPC23170
0.7843	Intermediate Similarity	NPC8993
0.7838	Intermediate Similarity	NPC90952
0.7838	Intermediate Similarity	NPC277769
0.7835	Intermediate Similarity	NPC476412
0.783	Intermediate Similarity	NPC136289
0.7826	Intermediate Similarity	NPC478051
0.7822	Intermediate Similarity	NPC473998
0.7822	Intermediate Similarity	NPC475806
0.7822	Intermediate Similarity	NPC99380
0.7822	Intermediate Similarity	NPC472975
0.7818	Intermediate Similarity	NPC76084
0.7812	Intermediate Similarity	NPC93590
0.781	Intermediate Similarity	NPC327431
0.781	Intermediate Similarity	NPC474012
0.781	Intermediate Similarity	NPC46761
0.781	Intermediate Similarity	NPC174314
0.781	Intermediate Similarity	NPC476299
0.781	Intermediate Similarity	NPC470074
0.7807	Intermediate Similarity	NPC709
0.7807	Intermediate Similarity	NPC21326
0.7807	Intermediate Similarity	NPC50774
0.78	Intermediate Similarity	NPC472475
0.78	Intermediate Similarity	NPC472477
0.78	Intermediate Similarity	NPC473999
0.78	Intermediate Similarity	NPC309603
0.7798	Intermediate Similarity	NPC151393
0.7798	Intermediate Similarity	NPC192813
0.7798	Intermediate Similarity	NPC277017
0.7798	Intermediate Similarity	NPC154608
0.7798	Intermediate Similarity	NPC102843
0.7788	Intermediate Similarity	NPC270478
0.7788	Intermediate Similarity	NPC207217
0.7778	Intermediate Similarity	NPC128828
0.7778	Intermediate Similarity	NPC120724
0.7778	Intermediate Similarity	NPC298904
0.7778	Intermediate Similarity	NPC469789
0.7769	Intermediate Similarity	NPC476193
0.7768	Intermediate Similarity	NPC208998
0.7768	Intermediate Similarity	NPC7921
0.7768	Intermediate Similarity	NPC317210
0.7767	Intermediate Similarity	NPC472485
0.7767	Intermediate Similarity	NPC280725
0.7757	Intermediate Similarity	NPC118902
0.7757	Intermediate Similarity	NPC469980
0.7757	Intermediate Similarity	NPC311612
0.7757	Intermediate Similarity	NPC104161
0.7757	Intermediate Similarity	NPC275583
0.7755	Intermediate Similarity	NPC79573
0.7755	Intermediate Similarity	NPC263997
0.7755	Intermediate Similarity	NPC132228
0.7755	Intermediate Similarity	NPC15807
0.7755	Intermediate Similarity	NPC70685
0.7755	Intermediate Similarity	NPC8518
0.7748	Intermediate Similarity	NPC472928
0.7748	Intermediate Similarity	NPC474229
0.7736	Intermediate Similarity	NPC472643
0.7736	Intermediate Similarity	NPC476897
0.7736	Intermediate Similarity	NPC472637
0.7736	Intermediate Similarity	NPC115862
0.7736	Intermediate Similarity	NPC97435
0.7731	Intermediate Similarity	NPC473253
0.7727	Intermediate Similarity	NPC470615
0.7723	Intermediate Similarity	NPC473099
0.7723	Intermediate Similarity	NPC48010
0.7723	Intermediate Similarity	NPC113393
0.7723	Intermediate Similarity	NPC232202
0.7723	Intermediate Similarity	NPC134321
0.7719	Intermediate Similarity	NPC183580
0.7719	Intermediate Similarity	NPC140055
0.7719	Intermediate Similarity	NPC470492
0.7719	Intermediate Similarity	NPC470493
0.7719	Intermediate Similarity	NPC474518
0.7719	Intermediate Similarity	NPC286528
0.7719	Intermediate Similarity	NPC20302
0.7719	Intermediate Similarity	NPC167606
0.7719	Intermediate Similarity	NPC469684
0.7719	Intermediate Similarity	NPC312824
0.7719	Intermediate Similarity	NPC239273
0.7714	Intermediate Similarity	NPC103051
0.7712	Intermediate Similarity	NPC8374
0.7712	Intermediate Similarity	NPC24651
0.7708	Intermediate Similarity	NPC14151
0.7708	Intermediate Similarity	NPC116797
0.7706	Intermediate Similarity	NPC44063
0.7706	Intermediate Similarity	NPC475060
0.7706	Intermediate Similarity	NPC475294
0.7706	Intermediate Similarity	NPC220229
0.7706	Intermediate Similarity	NPC3316
0.7706	Intermediate Similarity	NPC230541
0.7706	Intermediate Similarity	NPC144854
0.77	Intermediate Similarity	NPC58271
0.77	Intermediate Similarity	NPC48107
0.77	Intermediate Similarity	NPC307298
0.7699	Intermediate Similarity	NPC117712
0.7699	Intermediate Similarity	NPC80650
0.7692	Intermediate Similarity	NPC134072
0.7692	Intermediate Similarity	NPC117133
0.7692	Intermediate Similarity	NPC234993
0.7692	Intermediate Similarity	NPC184065
0.7692	Intermediate Similarity	NPC61369
0.7692	Intermediate Similarity	NPC471463
0.7692	Intermediate Similarity	NPC5532
0.7692	Intermediate Similarity	NPC242848

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 NPC131366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1605
0.2-0.3	3708
0.3-0.4	2415
0.4-0.5	770
0.5-0.6	210
0.6-0.7	193
0.7-0.8	54
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
0.783	Intermediate Similarity	NPD5211	Phase 2
0.7719	Intermediate Similarity	NPD7115	Discovery
0.7706	Intermediate Similarity	NPD5697	Approved
0.7685	Intermediate Similarity	NPD5141	Approved
0.7658	Intermediate Similarity	NPD4634	Approved
0.7642	Intermediate Similarity	NPD5286	Approved
0.7642	Intermediate Similarity	NPD4696	Approved
0.7642	Intermediate Similarity	NPD5285	Approved
0.7636	Intermediate Similarity	NPD6011	Approved
0.7636	Intermediate Similarity	NPD6881	Approved
0.7636	Intermediate Similarity	NPD6899	Approved
0.7619	Intermediate Similarity	NPD4755	Approved
0.7615	Intermediate Similarity	NPD6675	Approved
0.7615	Intermediate Similarity	NPD6402	Approved
0.7615	Intermediate Similarity	NPD7128	Approved
0.7615	Intermediate Similarity	NPD5739	Approved
0.7604	Intermediate Similarity	NPD4695	Discontinued
0.7589	Intermediate Similarity	NPD6650	Approved
0.7589	Intermediate Similarity	NPD6649	Approved
0.757	Intermediate Similarity	NPD5223	Approved
0.7568	Intermediate Similarity	NPD6372	Approved
0.7568	Intermediate Similarity	NPD6373	Approved
0.7568	Intermediate Similarity	NPD6013	Approved
0.7568	Intermediate Similarity	NPD6012	Approved
0.7568	Intermediate Similarity	NPD6014	Approved
0.7545	Intermediate Similarity	NPD5701	Approved
0.7524	Intermediate Similarity	NPD4697	Phase 3
0.7524	Intermediate Similarity	NPD5221	Approved
0.7524	Intermediate Similarity	NPD5222	Approved
0.7524	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD6319	Approved
0.7521	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD7102	Approved
0.7477	Intermediate Similarity	NPD4700	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7458	Intermediate Similarity	NPD6016	Approved
0.7458	Intermediate Similarity	NPD6015	Approved
0.7453	Intermediate Similarity	NPD6083	Phase 2
0.7453	Intermediate Similarity	NPD7902	Approved
0.7453	Intermediate Similarity	NPD6084	Phase 2
0.7453	Intermediate Similarity	NPD5173	Approved
0.7451	Intermediate Similarity	NPD4753	Phase 2
0.7449	Intermediate Similarity	NPD3667	Approved
0.7434	Intermediate Similarity	NPD6617	Approved
0.7434	Intermediate Similarity	NPD6869	Approved
0.7434	Intermediate Similarity	NPD6847	Approved
0.7434	Intermediate Similarity	NPD8130	Phase 1
0.7431	Intermediate Similarity	NPD5175	Approved
0.7431	Intermediate Similarity	NPD5174	Approved
0.7404	Intermediate Similarity	NPD6399	Phase 3
0.7404	Intermediate Similarity	NPD4202	Approved
0.7395	Intermediate Similarity	NPD6370	Approved
0.7395	Intermediate Similarity	NPD5988	Approved
0.7373	Intermediate Similarity	NPD6059	Approved
0.7368	Intermediate Similarity	NPD6882	Approved
0.7368	Intermediate Similarity	NPD8297	Approved
0.7333	Intermediate Similarity	NPD7748	Approved
0.7327	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7640	Approved
0.7315	Intermediate Similarity	NPD7639	Approved
0.7308	Intermediate Similarity	NPD7515	Phase 2
0.7308	Intermediate Similarity	NPD6079	Approved
0.7304	Intermediate Similarity	NPD4632	Approved
0.73	Intermediate Similarity	NPD3665	Phase 1
0.73	Intermediate Similarity	NPD3133	Approved
0.73	Intermediate Similarity	NPD3666	Approved
0.73	Intermediate Similarity	NPD4786	Approved
0.7297	Intermediate Similarity	NPD6008	Approved
0.7282	Intermediate Similarity	NPD5328	Approved
0.7281	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4754	Approved
0.7273	Intermediate Similarity	NPD7492	Approved
0.7265	Intermediate Similarity	NPD6009	Approved
0.7264	Intermediate Similarity	NPD5210	Approved
0.7264	Intermediate Similarity	NPD4629	Approved
0.7264	Intermediate Similarity	NPD5695	Phase 3
0.7257	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD1696	Phase 3
0.7222	Intermediate Similarity	NPD7638	Approved
0.7222	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD5696	Approved
0.7213	Intermediate Similarity	NPD6616	Approved
0.7193	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7604	Phase 2
0.7184	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD6672	Approved
0.7179	Intermediate Similarity	NPD6274	Approved
0.717	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5282	Discontinued
0.717	Intermediate Similarity	NPD7900	Approved
0.7168	Intermediate Similarity	NPD4729	Approved
0.7168	Intermediate Similarity	NPD5128	Approved
0.7168	Intermediate Similarity	NPD4730	Approved
0.7167	Intermediate Similarity	NPD5983	Phase 2
0.7157	Intermediate Similarity	NPD4623	Approved
0.7157	Intermediate Similarity	NPD4519	Discontinued
0.7157	Intermediate Similarity	NPD5279	Phase 3
0.7154	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD4767	Approved
0.7129	Intermediate Similarity	NPD4197	Approved
0.7119	Intermediate Similarity	NPD6317	Approved
0.7097	Intermediate Similarity	NPD7736	Approved
0.7075	Intermediate Similarity	NPD5778	Approved
0.7075	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD5329	Approved
0.7059	Intermediate Similarity	NPD6335	Approved
0.7059	Intermediate Similarity	NPD6314	Approved
0.7059	Intermediate Similarity	NPD6313	Approved
0.7049	Intermediate Similarity	NPD8328	Phase 3
0.7043	Intermediate Similarity	NPD5247	Approved
0.7043	Intermediate Similarity	NPD5248	Approved
0.7043	Intermediate Similarity	NPD5135	Approved
0.7043	Intermediate Similarity	NPD5169	Approved
0.7043	Intermediate Similarity	NPD5249	Phase 3
0.7043	Intermediate Similarity	NPD5250	Approved
0.7043	Intermediate Similarity	NPD5251	Approved
0.7043	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD7101	Approved
0.699	Remote Similarity	NPD5690	Phase 2
0.6983	Remote Similarity	NPD5217	Approved
0.6983	Remote Similarity	NPD5127	Approved
0.6983	Remote Similarity	NPD5216	Approved
0.6983	Remote Similarity	NPD5215	Approved
0.6981	Remote Similarity	NPD5693	Phase 1
0.6961	Remote Similarity	NPD3668	Phase 3
0.696	Remote Similarity	NPD6033	Approved
0.6952	Remote Similarity	NPD6904	Approved
0.6952	Remote Similarity	NPD6673	Approved
0.6952	Remote Similarity	NPD6080	Approved
0.6935	Remote Similarity	NPD6336	Discontinued
0.6931	Remote Similarity	NPD4223	Phase 3
0.6931	Remote Similarity	NPD4221	Approved
0.693	Remote Similarity	NPD6412	Phase 2
0.693	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3573	Approved
0.6891	Remote Similarity	NPD6868	Approved
0.687	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6686	Approved
0.687	Remote Similarity	NPD5168	Approved
0.6869	Remote Similarity	NPD3617	Approved
0.686	Remote Similarity	NPD4522	Approved
0.6827	Remote Similarity	NPD6684	Approved
0.6827	Remote Similarity	NPD5280	Approved
0.6827	Remote Similarity	NPD7146	Approved
0.6827	Remote Similarity	NPD6409	Approved
0.6827	Remote Similarity	NPD7334	Approved
0.6827	Remote Similarity	NPD7521	Approved
0.6827	Remote Similarity	NPD5330	Approved
0.6827	Remote Similarity	NPD4694	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.6807	Remote Similarity	NPD5167	Approved
0.6792	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6371	Approved
0.6748	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6908	Approved
0.6748	Remote Similarity	NPD6909	Approved
0.6733	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5692	Phase 3
0.6726	Remote Similarity	NPD7632	Discontinued
0.6719	Remote Similarity	NPD5956	Approved
0.6698	Remote Similarity	NPD6903	Approved
0.6698	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD6098	Approved
0.6637	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6635	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD46	Approved
0.6574	Remote Similarity	NPD6698	Approved
0.6574	Remote Similarity	NPD5785	Approved
0.6571	Remote Similarity	NPD1694	Approved
0.6569	Remote Similarity	NPD7525	Registered
0.6538	Remote Similarity	NPD6695	Phase 3
0.6538	Remote Similarity	NPD4788	Approved
0.6525	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8035	Phase 2
0.6514	Remote Similarity	NPD8034	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