NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	278.135
LogP:	1.449
LogD:	1.357
LogS:	-3.039
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	4.616
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:	-4.556
MDCK Permeability:	2.4153090635081753e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.363
Human Intestinal Absorption (HIA):	0.125
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	50.08786392211914%
Volume Distribution (VD):	1.546
Pgp-substrate:	59.236114501953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.418
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.331
CYP3A4-substrate:	0.686

ADMET: Excretion

Clearance (CL):	4.721
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.934
Rat Oral Acute Toxicity:	0.913
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.894
Carcinogencity:	0.918
Eye Corrosion:	0.906
Eye Irritation:	0.509
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC172101

Natural Product ID:	NPC172101
*Common Name:**	Mukaadial
IUPAC Name:	(1S,4S,4aS,8aS)-1,4-dihydroxy-5,5,8a-trimethyl-4a,6,7,8-tetrahydro-4H-naphthalene-1,2-dicarbaldehyde
Synonyms:	Mukaadial
Standard InCHIKey:	AMHCJQBKGMEAAJ-NZBPQXDJSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-13(2)5-4-6-14(3)12(13)11(18)7-10(8-16)15(14,19)9-17/h7-9,11-12,18-19H,4-6H2,1-3H3/t11-,12-,14-,15+/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1[C@H](C=C(C=O)[C@@]2(C=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455627
PubChem CID:	159088
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO7432	Pleodendron costaricense	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872133]
NPO23467	Lobaria scrobiculata	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24725159]
NPO15593	Warburgia stuhlmannii	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15593	Warburgia stuhlmannii	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO602	Kielmeyera lathrophyton	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12548	Jahnoporus hirtus	Species	Albatrellaceae	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]
NPO15593	Warburgia stuhlmannii	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7432	Pleodendron costaricense	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]
NPO4356	Eugenia wallichii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14437	Rimularia gibbosa	Species	Trapeliaceae	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	17
Others	1

Activity Type	# Activity
Organism	18

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[532520]
NPT770	Organism	Rhizopus microsporus var. chinensis	Rhizopus microsporus var. chinensis	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT768	Organism	Sclerotinia	Sclerotinia	MIC	=	100.0	ug.mL-1	PMID[532520]
NPT772	Organism	Pichia anomala	Wickerhamomyces anomalus	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT771	Organism	Penicillium crustosum	Penicillium crustosum	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT769	Organism	Mucor mucedo	Mucor mucedo	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT767	Organism	Pichia jadinii	Cyberlindnera jadinii	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[532520]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1000.0	ug.mL-1	PMID[532521]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	250.0	ug.mL-1	PMID[532521]
NPT20	Organism	Candida albicans	Candida albicans	FICI	=	0.8	n.a.	PMID[532521]

☑ 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 NPC172101 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	1230
0.2-0.3	5215
0.3-0.4	11227
0.4-0.5	12857
0.5-0.6	7253
0.6-0.7	4057
0.7-0.8	646
0.8-0.85	21
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC70685
0.9032	High Similarity	NPC174314
0.8571	High Similarity	NPC1679
0.8523	High Similarity	NPC470812
0.8462	Intermediate Similarity	NPC472983
0.837	Intermediate Similarity	NPC134321
0.837	Intermediate Similarity	NPC230332
0.828	Intermediate Similarity	NPC99380
0.8276	Intermediate Similarity	NPC472301
0.8222	Intermediate Similarity	NPC476426
0.8172	Intermediate Similarity	NPC128672
0.8161	Intermediate Similarity	NPC152061
0.8132	Intermediate Similarity	NPC194417
0.8105	Intermediate Similarity	NPC196227
0.8085	Intermediate Similarity	NPC472978
0.8068	Intermediate Similarity	NPC157895
0.8068	Intermediate Similarity	NPC104120
0.8068	Intermediate Similarity	NPC148685
0.8065	Intermediate Similarity	NPC472973
0.8046	Intermediate Similarity	NPC62336
0.8043	Intermediate Similarity	NPC220930
0.8043	Intermediate Similarity	NPC272039
0.8022	Intermediate Similarity	NPC255174
0.8021	Intermediate Similarity	NPC476245
0.8	Intermediate Similarity	NPC131366
0.8	Intermediate Similarity	NPC64600
0.798	Intermediate Similarity	NPC470184
0.7978	Intermediate Similarity	NPC119229
0.7978	Intermediate Similarity	NPC116797
0.7957	Intermediate Similarity	NPC471793
0.7957	Intermediate Similarity	NPC471791
0.7955	Intermediate Similarity	NPC308038
0.7938	Intermediate Similarity	NPC192428
0.7935	Intermediate Similarity	NPC198761
0.7935	Intermediate Similarity	NPC472974
0.7935	Intermediate Similarity	NPC470955
0.7917	Intermediate Similarity	NPC472977
0.7917	Intermediate Similarity	NPC472976
0.7912	Intermediate Similarity	NPC476412
0.7912	Intermediate Similarity	NPC40687
0.7895	Intermediate Similarity	NPC116726
0.7889	Intermediate Similarity	NPC279186
0.7889	Intermediate Similarity	NPC470813
0.7872	Intermediate Similarity	NPC123912
0.7865	Intermediate Similarity	NPC172013
0.7865	Intermediate Similarity	NPC471514
0.7857	Intermediate Similarity	NPC273269
0.7857	Intermediate Similarity	NPC471916
0.7841	Intermediate Similarity	NPC253561
0.7841	Intermediate Similarity	NPC475994
0.7841	Intermediate Similarity	NPC478122
0.7841	Intermediate Similarity	NPC80088
0.7826	Intermediate Similarity	NPC79573
0.7816	Intermediate Similarity	NPC263582
0.7812	Intermediate Similarity	NPC472930
0.7802	Intermediate Similarity	NPC105173
0.78	Intermediate Similarity	NPC472924
0.78	Intermediate Similarity	NPC163372
0.78	Intermediate Similarity	NPC302537
0.7778	Intermediate Similarity	NPC316598
0.7778	Intermediate Similarity	NPC226068
0.7767	Intermediate Similarity	NPC472925
0.7766	Intermediate Similarity	NPC473229
0.7766	Intermediate Similarity	NPC474854
0.7766	Intermediate Similarity	NPC474925
0.7755	Intermediate Similarity	NPC184065
0.7755	Intermediate Similarity	NPC61369
0.7755	Intermediate Similarity	NPC469545
0.7755	Intermediate Similarity	NPC5532
0.7755	Intermediate Similarity	NPC249954
0.7753	Intermediate Similarity	NPC281138
0.7742	Intermediate Similarity	NPC473226
0.7742	Intermediate Similarity	NPC34190
0.7727	Intermediate Similarity	NPC197659
0.7727	Intermediate Similarity	NPC74995
0.7723	Intermediate Similarity	NPC119601
0.7723	Intermediate Similarity	NPC308726
0.7723	Intermediate Similarity	NPC87351
0.7717	Intermediate Similarity	NPC227132
0.7708	Intermediate Similarity	NPC73457
0.7708	Intermediate Similarity	NPC168027
0.7708	Intermediate Similarity	NPC472975
0.7708	Intermediate Similarity	NPC185936
0.77	Intermediate Similarity	NPC144956
0.7692	Intermediate Similarity	NPC476802
0.7692	Intermediate Similarity	NPC93590
0.7692	Intermediate Similarity	NPC89171
0.7692	Intermediate Similarity	NPC103486
0.7684	Intermediate Similarity	NPC472676
0.7684	Intermediate Similarity	NPC184663
0.7684	Intermediate Similarity	NPC472688
0.7677	Intermediate Similarity	NPC18509
0.767	Intermediate Similarity	NPC32006
0.767	Intermediate Similarity	NPC85529
0.7667	Intermediate Similarity	NPC45495
0.7667	Intermediate Similarity	NPC271104
0.7653	Intermediate Similarity	NPC316215
0.7653	Intermediate Similarity	NPC272617
0.7653	Intermediate Similarity	NPC259286
0.7647	Intermediate Similarity	NPC230918
0.7647	Intermediate Similarity	NPC311612
0.7647	Intermediate Similarity	NPC111323
0.7634	Intermediate Similarity	NPC179006
0.7634	Intermediate Similarity	NPC474853
0.7629	Intermediate Similarity	NPC474807
0.7629	Intermediate Similarity	NPC476416
0.7629	Intermediate Similarity	NPC115021
0.7629	Intermediate Similarity	NPC69454
0.7624	Intermediate Similarity	NPC112613
0.7624	Intermediate Similarity	NPC207885
0.7614	Intermediate Similarity	NPC151622
0.7614	Intermediate Similarity	NPC7629
0.7609	Intermediate Similarity	NPC307258
0.76	Intermediate Similarity	NPC23364
0.76	Intermediate Similarity	NPC147954
0.7596	Intermediate Similarity	NPC185
0.7586	Intermediate Similarity	NPC215050
0.7582	Intermediate Similarity	NPC6663
0.7579	Intermediate Similarity	NPC53454
0.7579	Intermediate Similarity	NPC72397
0.7579	Intermediate Similarity	NPC58271
0.7579	Intermediate Similarity	NPC206060
0.7579	Intermediate Similarity	NPC307298
0.7579	Intermediate Similarity	NPC104560
0.7576	Intermediate Similarity	NPC471463
0.7576	Intermediate Similarity	NPC94337
0.7556	Intermediate Similarity	NPC19900
0.7556	Intermediate Similarity	NPC7232
0.7553	Intermediate Similarity	NPC327115
0.7553	Intermediate Similarity	NPC476043
0.7553	Intermediate Similarity	NPC472986
0.7553	Intermediate Similarity	NPC472985
0.7551	Intermediate Similarity	NPC103527
0.7551	Intermediate Similarity	NPC292793
0.7551	Intermediate Similarity	NPC299100
0.7549	Intermediate Similarity	NPC195290
0.7549	Intermediate Similarity	NPC204450
0.7549	Intermediate Similarity	NPC473424
0.7547	Intermediate Similarity	NPC5103
0.7528	Intermediate Similarity	NPC257666
0.7528	Intermediate Similarity	NPC266193
0.7528	Intermediate Similarity	NPC34110
0.7527	Intermediate Similarity	NPC230527
0.7527	Intermediate Similarity	NPC7927
0.7526	Intermediate Similarity	NPC63748
0.7526	Intermediate Similarity	NPC475441
0.7525	Intermediate Similarity	NPC51370
0.7525	Intermediate Similarity	NPC476274
0.7525	Intermediate Similarity	NPC46761
0.7525	Intermediate Similarity	NPC287833
0.7525	Intermediate Similarity	NPC472644
0.7524	Intermediate Similarity	NPC295244
0.75	Intermediate Similarity	NPC56448
0.75	Intermediate Similarity	NPC38796
0.75	Intermediate Similarity	NPC472971
0.75	Intermediate Similarity	NPC284365
0.75	Intermediate Similarity	NPC70479
0.75	Intermediate Similarity	NPC123726
0.75	Intermediate Similarity	NPC158411
0.75	Intermediate Similarity	NPC472970
0.7477	Intermediate Similarity	NPC472928
0.7476	Intermediate Similarity	NPC90177
0.7476	Intermediate Similarity	NPC236390
0.7475	Intermediate Similarity	NPC318282
0.7475	Intermediate Similarity	NPC472932
0.7475	Intermediate Similarity	NPC183012
0.7475	Intermediate Similarity	NPC469995
0.7475	Intermediate Similarity	NPC174948
0.7475	Intermediate Similarity	NPC280725
0.7475	Intermediate Similarity	NPC474602
0.7475	Intermediate Similarity	NPC173875
0.7475	Intermediate Similarity	NPC134067
0.7475	Intermediate Similarity	NPC266899
0.7475	Intermediate Similarity	NPC180950
0.7473	Intermediate Similarity	NPC306095
0.7471	Intermediate Similarity	NPC186042
0.7453	Intermediate Similarity	NPC87335
0.7453	Intermediate Similarity	NPC20192
0.7453	Intermediate Similarity	NPC214644
0.7451	Intermediate Similarity	NPC476223
0.7451	Intermediate Similarity	NPC476240
0.7451	Intermediate Similarity	NPC224720
0.7451	Intermediate Similarity	NPC472637
0.7451	Intermediate Similarity	NPC81530
0.7451	Intermediate Similarity	NPC282524
0.7449	Intermediate Similarity	NPC151722
0.7449	Intermediate Similarity	NPC477436
0.7449	Intermediate Similarity	NPC477435
0.7449	Intermediate Similarity	NPC477520
0.7449	Intermediate Similarity	NPC131840
0.7447	Intermediate Similarity	NPC471344
0.7447	Intermediate Similarity	NPC36350
0.7447	Intermediate Similarity	NPC15807
0.7447	Intermediate Similarity	NPC32037
0.7444	Intermediate Similarity	NPC207772
0.7444	Intermediate Similarity	NPC471409
0.7444	Intermediate Similarity	NPC178852
0.7444	Intermediate Similarity	NPC275494
0.7431	Intermediate Similarity	NPC238667
0.7429	Intermediate Similarity	NPC43285

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 NPC172101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1670
0.2-0.3	3918
0.3-0.4	2318
0.4-0.5	669
0.5-0.6	218
0.6-0.7	168
0.7-0.8	17
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
0.7938	Intermediate Similarity	NPD4697	Phase 3
0.79	Intermediate Similarity	NPD5211	Phase 2
0.7745	Intermediate Similarity	NPD5141	Approved
0.77	Intermediate Similarity	NPD5285	Approved
0.77	Intermediate Similarity	NPD4696	Approved
0.77	Intermediate Similarity	NPD5286	Approved
0.7677	Intermediate Similarity	NPD4755	Approved
0.7624	Intermediate Similarity	NPD5223	Approved
0.7576	Intermediate Similarity	NPD5222	Approved
0.7576	Intermediate Similarity	NPD5221	Approved
0.7576	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD5226	Approved
0.7549	Intermediate Similarity	NPD4633	Approved
0.7549	Intermediate Similarity	NPD5225	Approved
0.7549	Intermediate Similarity	NPD5224	Approved
0.7525	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.7476	Intermediate Similarity	NPD5174	Approved
0.7476	Intermediate Similarity	NPD5175	Approved
0.7383	Intermediate Similarity	NPD4634	Approved
0.7347	Intermediate Similarity	NPD6079	Approved
0.732	Intermediate Similarity	NPD4753	Phase 2
0.732	Intermediate Similarity	NPD5328	Approved
0.7308	Intermediate Similarity	NPD4754	Approved
0.7283	Intermediate Similarity	NPD4695	Discontinued
0.7264	Intermediate Similarity	NPD5697	Approved
0.7263	Intermediate Similarity	NPD1696	Phase 3
0.7196	Intermediate Similarity	NPD6899	Approved
0.7196	Intermediate Similarity	NPD5128	Approved
0.7196	Intermediate Similarity	NPD4730	Approved
0.7196	Intermediate Similarity	NPD6011	Approved
0.7196	Intermediate Similarity	NPD6881	Approved
0.7196	Intermediate Similarity	NPD4729	Approved
0.7188	Intermediate Similarity	NPD5279	Phase 3
0.7188	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3618	Phase 1
0.717	Intermediate Similarity	NPD7128	Approved
0.717	Intermediate Similarity	NPD6675	Approved
0.717	Intermediate Similarity	NPD5739	Approved
0.717	Intermediate Similarity	NPD4768	Approved
0.717	Intermediate Similarity	NPD4767	Approved
0.717	Intermediate Similarity	NPD6402	Approved
0.7158	Intermediate Similarity	NPD3133	Approved
0.7158	Intermediate Similarity	NPD3666	Approved
0.7158	Intermediate Similarity	NPD3665	Phase 1
0.7156	Intermediate Similarity	NPD6650	Approved
0.7156	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6012	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD6014	Approved
0.7129	Intermediate Similarity	NPD5210	Approved
0.7129	Intermediate Similarity	NPD4629	Approved
0.7103	Intermediate Similarity	NPD5701	Approved
0.71	Intermediate Similarity	NPD4202	Approved
0.7064	Intermediate Similarity	NPD7102	Approved
0.7064	Intermediate Similarity	NPD5249	Phase 3
0.7064	Intermediate Similarity	NPD5251	Approved
0.7064	Intermediate Similarity	NPD7290	Approved
0.7064	Intermediate Similarity	NPD5248	Approved
0.7064	Intermediate Similarity	NPD5135	Approved
0.7064	Intermediate Similarity	NPD5247	Approved
0.7064	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5169	Approved
0.7064	Intermediate Similarity	NPD6883	Approved
0.7064	Intermediate Similarity	NPD5250	Approved
0.7037	Intermediate Similarity	NPD7320	Approved
0.701	Intermediate Similarity	NPD4623	Approved
0.701	Intermediate Similarity	NPD4519	Discontinued
0.701	Intermediate Similarity	NPD5690	Phase 2
0.7	Intermediate Similarity	NPD5215	Approved
0.7	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD8130	Phase 1
0.7	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD5217	Approved
0.7	Intermediate Similarity	NPD5216	Approved
0.7	Intermediate Similarity	NPD6847	Approved
0.7	Intermediate Similarity	NPD5127	Approved
0.7	Intermediate Similarity	NPD6869	Approved
0.6979	Remote Similarity	NPD4197	Approved
0.6947	Remote Similarity	NPD3667	Approved
0.6937	Remote Similarity	NPD6882	Approved
0.6937	Remote Similarity	NPD8297	Approved
0.6907	Remote Similarity	NPD5329	Approved
0.6881	Remote Similarity	NPD5168	Approved
0.6875	Remote Similarity	NPD4632	Approved
0.6847	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5280	Approved
0.6837	Remote Similarity	NPD4694	Approved
0.6827	Remote Similarity	NPD6084	Phase 2
0.6827	Remote Similarity	NPD7902	Approved
0.6827	Remote Similarity	NPD6083	Phase 2
0.6814	Remote Similarity	NPD5167	Approved
0.681	Remote Similarity	NPD6319	Approved
0.681	Remote Similarity	NPD6054	Approved
0.6804	Remote Similarity	NPD4786	Approved
0.6796	Remote Similarity	NPD5695	Phase 3
0.6771	Remote Similarity	NPD4223	Phase 3
0.6771	Remote Similarity	NPD4221	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.6765	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD4225	Approved
0.6754	Remote Similarity	NPD6274	Approved
0.6752	Remote Similarity	NPD6015	Approved
0.6752	Remote Similarity	NPD6016	Approved
0.6706	Remote Similarity	NPD368	Approved
0.6702	Remote Similarity	NPD3617	Approved
0.6699	Remote Similarity	NPD7748	Approved
0.6696	Remote Similarity	NPD7115	Discovery
0.6696	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6695	Remote Similarity	NPD6370	Approved
0.6695	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6638	Remote Similarity	NPD6314	Approved
0.6638	Remote Similarity	NPD6313	Approved
0.6638	Remote Similarity	NPD6335	Approved
0.6635	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5696	Approved
0.6602	Remote Similarity	NPD6399	Phase 3
0.66	Remote Similarity	NPD3573	Approved
0.6598	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7331	Phase 2
0.6583	Remote Similarity	NPD7492	Approved
0.6581	Remote Similarity	NPD7100	Approved
0.6581	Remote Similarity	NPD7101	Approved
0.6569	Remote Similarity	NPD5785	Approved
0.6566	Remote Similarity	NPD5363	Approved
0.6566	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7639	Approved
0.6542	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD7900	Approved
0.6535	Remote Similarity	NPD5737	Approved
0.6535	Remote Similarity	NPD6672	Approved
0.6529	Remote Similarity	NPD6616	Approved
0.6505	Remote Similarity	NPD5284	Approved
0.6505	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD4138	Approved
0.65	Remote Similarity	NPD4688	Approved
0.65	Remote Similarity	NPD5205	Approved
0.65	Remote Similarity	NPD4689	Approved
0.65	Remote Similarity	NPD5786	Approved
0.65	Remote Similarity	NPD4690	Approved
0.65	Remote Similarity	NPD4693	Phase 3
0.6475	Remote Similarity	NPD7078	Approved
0.6471	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5983	Phase 2
0.6466	Remote Similarity	NPD6868	Approved
0.6465	Remote Similarity	NPD3668	Phase 3
0.6449	Remote Similarity	NPD7638	Approved
0.6441	Remote Similarity	NPD4522	Approved
0.6429	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7736	Approved
0.6392	Remote Similarity	NPD7525	Registered
0.6371	Remote Similarity	NPD7319	Approved
0.6364	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD4788	Approved
0.6354	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5693	Phase 1
0.6341	Remote Similarity	NPD8293	Discontinued
0.6337	Remote Similarity	NPD6684	Approved
0.6337	Remote Similarity	NPD5330	Approved
0.6337	Remote Similarity	NPD7146	Approved
0.6337	Remote Similarity	NPD6409	Approved
0.6337	Remote Similarity	NPD7334	Approved
0.6337	Remote Similarity	NPD7521	Approved
0.6333	Remote Similarity	NPD6909	Approved
0.6333	Remote Similarity	NPD6908	Approved
0.6311	Remote Similarity	NPD6904	Approved
0.6311	Remote Similarity	NPD6673	Approved
0.6311	Remote Similarity	NPD6080	Approved
0.6304	Remote Similarity	NPD4691	Approved
0.6292	Remote Similarity	NPD7341	Phase 2
0.629	Remote Similarity	NPD6033	Approved
0.6289	Remote Similarity	NPD4195	Approved
0.6286	Remote Similarity	NPD5133	Approved
0.6283	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6686	Approved
0.6273	Remote Similarity	NPD5091	Approved
0.6263	Remote Similarity	NPD4269	Approved
0.6263	Remote Similarity	NPD4270	Approved
0.626	Remote Similarity	NPD7507	Approved
0.626	Remote Similarity	NPD6336	Discontinued
0.625	Remote Similarity	NPD5692	Phase 3
0.625	Remote Similarity	NPD6008	Approved
0.6228	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6903	Approved
0.6211	Remote Similarity	NPD8264	Approved
0.6207	Remote Similarity	NPD6053	Discontinued
0.62	Remote Similarity	NPD6110	Phase 1

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