NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.15
Volume:	249.178
LogP:	0.738
LogD:	0.106
LogS:	-2.432
# Rotatable Bonds:	3
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.742
Synthetic Accessibility Score:	4.424
Fsp3:	0.5
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:	-4.459
MDCK Permeability:	1.876365058706142e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272
Plasma Protein Binding (PPB):	67.0099105834961%
Volume Distribution (VD):	0.534
Pgp-substrate:	26.799440383911133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.225
CYP1A2-substrate:	0.649
CYP2C19-inhibitor:	0.192
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.615
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.635
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	5.681
Half-life (T1/2):	0.609

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.628
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.425
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.558
Carcinogencity:	0.39
Eye Corrosion:	0.517
Eye Irritation:	0.958
Respiratory Toxicity:	0.736

Download Data

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

Natural Product: NPC476649

Natural Product ID:	NPC476649
*Common Name:**	(2R)-2alpha-Methyl-3beta-[(1E,3E,5E)-1,3,5-heptatrienyl]-5beta-hydroxycyclohexanone
IUPAC Name:	(2R,3R,5R)-3-[(1E,3E,5E)-hepta-1,3,5-trienyl]-5-hydroxy-2-methylcyclohexan-1-one
Synonyms:	Waikialide A
Standard InCHIKey:	JQUGOGSMHDBLNB-BIOSCNBNSA-N
Standard InCHI:	InChI=1S/C14H20O2/c1-3-4-5-6-7-8-12-9-13(15)10-14(16)11(12)2/h3-8,11-13,15H,9-10H2,1-2H3/b4-3+,6-5+,8-7+/t11-,12+,13-/m1/s1
SMILES:	C/C=C/C=C/C=C/[C@H]1C[C@H](CC(=O)[C@@H]1C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57408410
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	1
MIC	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	200000	nM	PMID[22400916]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	32400	nM	PMID[22400916]

☑ 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 NPC476649 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	153
0.1-0.2	981
0.2-0.3	5425
0.3-0.4	14156
0.4-0.5	12540
0.5-0.6	7362
0.6-0.7	1953
0.7-0.8	124
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8718	High Similarity	NPC136114
0.7952	Intermediate Similarity	NPC298904
0.7875	Intermediate Similarity	NPC14151
0.775	Intermediate Similarity	NPC148685
0.775	Intermediate Similarity	NPC157895
0.775	Intermediate Similarity	NPC104120
0.7722	Intermediate Similarity	NPC178852
0.7683	Intermediate Similarity	NPC64600
0.7683	Intermediate Similarity	NPC105173
0.7683	Intermediate Similarity	NPC312480
0.7619	Intermediate Similarity	NPC475753
0.7595	Intermediate Similarity	NPC197659
0.7568	Intermediate Similarity	NPC476650
0.7558	Intermediate Similarity	NPC118193
0.7558	Intermediate Similarity	NPC97577
0.7558	Intermediate Similarity	NPC256902
0.7558	Intermediate Similarity	NPC69627
0.7529	Intermediate Similarity	NPC472324
0.7529	Intermediate Similarity	NPC141292
0.747	Intermediate Similarity	NPC476082
0.747	Intermediate Similarity	NPC278648
0.7468	Intermediate Similarity	NPC250621
0.7442	Intermediate Similarity	NPC158778
0.7442	Intermediate Similarity	NPC292491
0.7442	Intermediate Similarity	NPC310752
0.7412	Intermediate Similarity	NPC183736
0.7412	Intermediate Similarity	NPC262026
0.7407	Intermediate Similarity	NPC474113
0.7407	Intermediate Similarity	NPC308038
0.7403	Intermediate Similarity	NPC320119
0.7386	Intermediate Similarity	NPC36491
0.7375	Intermediate Similarity	NPC74995
0.7368	Intermediate Similarity	NPC10758
0.7368	Intermediate Similarity	NPC250928
0.7349	Intermediate Similarity	NPC48362
0.7349	Intermediate Similarity	NPC93590
0.7342	Intermediate Similarity	NPC114236
0.7333	Intermediate Similarity	NPC280725
0.7333	Intermediate Similarity	NPC88310
0.7317	Intermediate Similarity	NPC172013
0.7308	Intermediate Similarity	NPC275098
0.7294	Intermediate Similarity	NPC202868
0.7294	Intermediate Similarity	NPC15807
0.7294	Intermediate Similarity	NPC79573
0.7284	Intermediate Similarity	NPC207772
0.7284	Intermediate Similarity	NPC62336
0.7273	Intermediate Similarity	NPC472325
0.7253	Intermediate Similarity	NPC471153
0.725	Intermediate Similarity	NPC1973
0.725	Intermediate Similarity	NPC167873
0.725	Intermediate Similarity	NPC263582
0.7241	Intermediate Similarity	NPC53911
0.7241	Intermediate Similarity	NPC328539
0.7229	Intermediate Similarity	NPC119229
0.7229	Intermediate Similarity	NPC121984
0.7229	Intermediate Similarity	NPC473420
0.7222	Intermediate Similarity	NPC474529
0.7209	Intermediate Similarity	NPC476043
0.7209	Intermediate Similarity	NPC198761
0.7209	Intermediate Similarity	NPC194417
0.7195	Intermediate Similarity	NPC229204
0.7195	Intermediate Similarity	NPC7232
0.7195	Intermediate Similarity	NPC152061
0.7176	Intermediate Similarity	NPC470812
0.716	Intermediate Similarity	NPC203403
0.716	Intermediate Similarity	NPC325946
0.716	Intermediate Similarity	NPC472746
0.7159	Intermediate Similarity	NPC275740
0.7159	Intermediate Similarity	NPC472970
0.7159	Intermediate Similarity	NPC472973
0.7159	Intermediate Similarity	NPC472971
0.7159	Intermediate Similarity	NPC86319
0.7158	Intermediate Similarity	NPC320294
0.7143	Intermediate Similarity	NPC151519
0.7143	Intermediate Similarity	NPC73882
0.7126	Intermediate Similarity	NPC136548
0.7111	Intermediate Similarity	NPC477520
0.7111	Intermediate Similarity	NPC134826
0.7108	Intermediate Similarity	NPC471514
0.7108	Intermediate Similarity	NPC306095
0.7108	Intermediate Similarity	NPC45495
0.7108	Intermediate Similarity	NPC164999
0.7105	Intermediate Similarity	NPC96962
0.7093	Intermediate Similarity	NPC470574
0.7093	Intermediate Similarity	NPC36350
0.7093	Intermediate Similarity	NPC133954
0.7089	Intermediate Similarity	NPC186042
0.7089	Intermediate Similarity	NPC326024
0.7089	Intermediate Similarity	NPC68443
0.7079	Intermediate Similarity	NPC128672
0.7079	Intermediate Similarity	NPC134321
0.7079	Intermediate Similarity	NPC230332
0.7073	Intermediate Similarity	NPC80088
0.7073	Intermediate Similarity	NPC297996
0.7073	Intermediate Similarity	NPC253561
0.7067	Intermediate Similarity	NPC474329
0.7067	Intermediate Similarity	NPC474304
0.7045	Intermediate Similarity	NPC131470
0.7045	Intermediate Similarity	NPC471724
0.7045	Intermediate Similarity	NPC143767
0.7045	Intermediate Similarity	NPC328313
0.7045	Intermediate Similarity	NPC474854
0.7037	Intermediate Similarity	NPC242722
0.7037	Intermediate Similarity	NPC78935
0.7037	Intermediate Similarity	NPC76966
0.7037	Intermediate Similarity	NPC472305
0.7037	Intermediate Similarity	NPC469514
0.7037	Intermediate Similarity	NPC470525
0.7037	Intermediate Similarity	NPC469646
0.7037	Intermediate Similarity	NPC186554
0.7033	Intermediate Similarity	NPC299100
0.7033	Intermediate Similarity	NPC209662
0.7033	Intermediate Similarity	NPC471207
0.7033	Intermediate Similarity	NPC473172
0.7033	Intermediate Similarity	NPC474690
0.7024	Intermediate Similarity	NPC136150
0.7024	Intermediate Similarity	NPC116797
0.7013	Intermediate Similarity	NPC477452
0.7013	Intermediate Similarity	NPC471238
0.7011	Intermediate Similarity	NPC473168
0.7011	Intermediate Similarity	NPC213412
0.7011	Intermediate Similarity	NPC472985
0.7011	Intermediate Similarity	NPC472986
0.7011	Intermediate Similarity	NPC20688
0.7011	Intermediate Similarity	NPC94666
0.7011	Intermediate Similarity	NPC475862
0.7011	Intermediate Similarity	NPC470955
0.7011	Intermediate Similarity	NPC179591
0.7011	Intermediate Similarity	NPC74363
0.7011	Intermediate Similarity	NPC202394
0.7	Intermediate Similarity	NPC472975
0.7	Intermediate Similarity	NPC19114
0.7	Intermediate Similarity	NPC301244
0.7	Intermediate Similarity	NPC473167
0.7	Intermediate Similarity	NPC3753
0.7	Intermediate Similarity	NPC472978
0.7	Intermediate Similarity	NPC237591
0.7	Intermediate Similarity	NPC168027
0.7	Intermediate Similarity	NPC185936
0.7	Intermediate Similarity	NPC230623
0.7	Intermediate Similarity	NPC102313
0.7	Intermediate Similarity	NPC199316
0.6989	Remote Similarity	NPC161147
0.6989	Remote Similarity	NPC21728
0.6988	Remote Similarity	NPC113363
0.6988	Remote Similarity	NPC164308
0.6988	Remote Similarity	NPC19900
0.6988	Remote Similarity	NPC281138
0.6977	Remote Similarity	NPC40687
0.6977	Remote Similarity	NPC180834
0.6977	Remote Similarity	NPC221758
0.6977	Remote Similarity	NPC59453
0.6966	Remote Similarity	NPC95246
0.6966	Remote Similarity	NPC161751
0.6966	Remote Similarity	NPC102414
0.6966	Remote Similarity	NPC474972
0.6966	Remote Similarity	NPC84271
0.6966	Remote Similarity	NPC77168
0.6957	Remote Similarity	NPC259286
0.6957	Remote Similarity	NPC180950
0.6957	Remote Similarity	NPC272617
0.6957	Remote Similarity	NPC127063
0.6951	Remote Similarity	NPC266193
0.6951	Remote Similarity	NPC276769
0.6951	Remote Similarity	NPC257666
0.6947	Remote Similarity	NPC282524
0.6941	Remote Similarity	NPC212083
0.6941	Remote Similarity	NPC70479
0.6932	Remote Similarity	NPC57469
0.6932	Remote Similarity	NPC58063
0.6932	Remote Similarity	NPC109900
0.6932	Remote Similarity	NPC287079
0.6932	Remote Similarity	NPC73064
0.6932	Remote Similarity	NPC86005
0.6923	Remote Similarity	NPC469914
0.6923	Remote Similarity	NPC475952
0.6923	Remote Similarity	NPC69454
0.6914	Remote Similarity	NPC472256
0.6914	Remote Similarity	NPC474011
0.6914	Remote Similarity	NPC476844
0.6905	Remote Similarity	NPC476809
0.6905	Remote Similarity	NPC115418
0.6905	Remote Similarity	NPC103634
0.6905	Remote Similarity	NPC233352
0.6905	Remote Similarity	NPC138492
0.6905	Remote Similarity	NPC824
0.6905	Remote Similarity	NPC74086
0.6905	Remote Similarity	NPC2482
0.6897	Remote Similarity	NPC474853
0.6897	Remote Similarity	NPC476426
0.6897	Remote Similarity	NPC179006
0.6889	Remote Similarity	NPC172361
0.6889	Remote Similarity	NPC129913
0.6889	Remote Similarity	NPC86372
0.6889	Remote Similarity	NPC183283
0.6883	Remote Similarity	NPC60120
0.6883	Remote Similarity	NPC278895
0.6882	Remote Similarity	NPC160056
0.6882	Remote Similarity	NPC249954
0.6882	Remote Similarity	NPC301534

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 NPC476649 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1443
0.2-0.3	4015
0.3-0.4	2486
0.4-0.5	663
0.5-0.6	326
0.6-0.7	73
0.7-0.8	3
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
0.7558	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6101	Approved
0.7386	Intermediate Similarity	NPD6411	Approved
0.7303	Intermediate Similarity	NPD5779	Approved
0.7303	Intermediate Similarity	NPD5778	Approved
0.7191	Intermediate Similarity	NPD6079	Approved
0.7159	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7011	Intermediate Similarity	NPD3618	Phase 1
0.7011	Intermediate Similarity	NPD5279	Phase 3
0.6977	Remote Similarity	NPD4786	Approved
0.6905	Remote Similarity	NPD4252	Approved
0.6905	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5368	Approved
0.6882	Remote Similarity	NPD5222	Approved
0.6882	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5221	Approved
0.6824	Remote Similarity	NPD5369	Approved
0.6818	Remote Similarity	NPD5786	Approved
0.6809	Remote Similarity	NPD5173	Approved
0.6782	Remote Similarity	NPD3666	Approved
0.6782	Remote Similarity	NPD3133	Approved
0.6782	Remote Similarity	NPD3665	Phase 1
0.6753	Remote Similarity	NPD7331	Phase 2
0.6744	Remote Similarity	NPD6435	Approved
0.6744	Remote Similarity	NPD4270	Approved
0.6744	Remote Similarity	NPD4269	Approved
0.6702	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4755	Approved
0.663	Remote Similarity	NPD7515	Phase 2
0.6623	Remote Similarity	NPD7341	Phase 2
0.6598	Remote Similarity	NPD5223	Approved
0.6559	Remote Similarity	NPD4202	Approved
0.6543	Remote Similarity	NPD7151	Approved
0.6543	Remote Similarity	NPD7152	Approved
0.6543	Remote Similarity	NPD7150	Approved
0.6531	Remote Similarity	NPD5224	Approved
0.6531	Remote Similarity	NPD5226	Approved
0.6531	Remote Similarity	NPD5225	Approved
0.6531	Remote Similarity	NPD4633	Approved
0.6531	Remote Similarity	NPD5211	Phase 2
0.6517	Remote Similarity	NPD5363	Approved
0.6506	Remote Similarity	NPD8264	Approved
0.6495	Remote Similarity	NPD4700	Approved
0.6465	Remote Similarity	NPD5175	Approved
0.6465	Remote Similarity	NPD5174	Approved
0.6452	Remote Similarity	NPD7983	Approved
0.6421	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7144	Approved
0.642	Remote Similarity	NPD7143	Approved
0.6408	Remote Similarity	NPD4634	Approved
0.6404	Remote Similarity	NPD3668	Phase 3
0.64	Remote Similarity	NPD5141	Approved
0.6386	Remote Similarity	NPD6926	Approved
0.6386	Remote Similarity	NPD6924	Approved
0.6354	Remote Similarity	NPD7839	Suspended
0.6333	Remote Similarity	NPD1696	Phase 3
0.6322	Remote Similarity	NPD4695	Discontinued
0.6316	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7748	Approved
0.63	Remote Similarity	NPD4754	Approved
0.6296	Remote Similarity	NPD6922	Approved
0.6296	Remote Similarity	NPD6923	Approved
0.6282	Remote Similarity	NPD3197	Phase 1
0.6277	Remote Similarity	NPD7637	Suspended
0.6275	Remote Similarity	NPD5697	Approved
0.6264	Remote Similarity	NPD4694	Approved
0.6264	Remote Similarity	NPD5280	Approved
0.6264	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4753	Phase 2
0.6235	Remote Similarity	NPD6933	Approved
0.6214	Remote Similarity	NPD5168	Approved
0.6214	Remote Similarity	NPD4730	Approved
0.6214	Remote Similarity	NPD6881	Approved
0.6214	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD6899	Approved
0.6214	Remote Similarity	NPD4729	Approved
0.6211	Remote Similarity	NPD6399	Phase 3
0.6196	Remote Similarity	NPD3573	Approved
0.618	Remote Similarity	NPD4223	Phase 3
0.618	Remote Similarity	NPD4221	Approved
0.6176	Remote Similarity	NPD6402	Approved
0.6176	Remote Similarity	NPD4767	Approved
0.6176	Remote Similarity	NPD7128	Approved
0.6176	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD4768	Approved
0.6176	Remote Similarity	NPD6675	Approved
0.617	Remote Similarity	NPD5785	Approved
0.6163	Remote Similarity	NPD6932	Approved
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6146	Remote Similarity	NPD5282	Discontinued
0.6136	Remote Similarity	NPD7509	Discontinued
0.6129	Remote Similarity	NPD4518	Approved
0.6122	Remote Similarity	NPD7902	Approved
0.6118	Remote Similarity	NPD3703	Phase 2
0.6117	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD5362	Discontinued
0.6105	Remote Similarity	NPD5281	Approved
0.6105	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5284	Approved
0.6098	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7290	Approved
0.6095	Remote Similarity	NPD7102	Approved
0.6095	Remote Similarity	NPD5248	Approved
0.6095	Remote Similarity	NPD5135	Approved
0.6095	Remote Similarity	NPD5249	Phase 3
0.6095	Remote Similarity	NPD5169	Approved
0.6095	Remote Similarity	NPD5247	Approved
0.6095	Remote Similarity	NPD5250	Approved
0.6095	Remote Similarity	NPD5251	Approved
0.6095	Remote Similarity	NPD6883	Approved
0.6092	Remote Similarity	NPD7145	Approved
0.6092	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4268	Approved
0.6092	Remote Similarity	NPD4271	Approved
0.6087	Remote Similarity	NPD4519	Discontinued
0.6087	Remote Similarity	NPD4623	Approved
0.6087	Remote Similarity	NPD5690	Phase 2
0.6082	Remote Similarity	NPD5210	Approved
0.6082	Remote Similarity	NPD4629	Approved
0.6058	Remote Similarity	NPD5128	Approved
0.6058	Remote Similarity	NPD7320	Approved
0.6047	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4197	Approved
0.6038	Remote Similarity	NPD5127	Approved
0.6038	Remote Similarity	NPD6847	Approved
0.6038	Remote Similarity	NPD6617	Approved
0.6038	Remote Similarity	NPD5216	Approved
0.6038	Remote Similarity	NPD6650	Approved
0.6038	Remote Similarity	NPD8130	Phase 1
0.6038	Remote Similarity	NPD5215	Approved
0.6038	Remote Similarity	NPD6649	Approved
0.6038	Remote Similarity	NPD6869	Approved
0.6038	Remote Similarity	NPD5217	Approved
0.6027	Remote Similarity	NPD3172	Approved
0.6026	Remote Similarity	NPD368	Approved
0.6023	Remote Similarity	NPD7645	Phase 2
0.6023	Remote Similarity	NPD6929	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD4096	Approved
0.6	Remote Similarity	NPD5209	Approved
0.6	Remote Similarity	NPD4687	Approved
0.6	Remote Similarity	NPD4058	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5981	Remote Similarity	NPD6882	Approved
0.5981	Remote Similarity	NPD8297	Approved
0.5978	Remote Similarity	NPD5329	Approved
0.5978	Remote Similarity	NPD1694	Approved
0.5977	Remote Similarity	NPD5776	Phase 2
0.5977	Remote Similarity	NPD6925	Approved
0.5955	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD4822	Approved
0.5955	Remote Similarity	NPD7525	Registered
0.5955	Remote Similarity	NPD6931	Approved
0.5955	Remote Similarity	NPD7514	Phase 3
0.5955	Remote Similarity	NPD4820	Approved
0.5955	Remote Similarity	NPD6930	Phase 2
0.5955	Remote Similarity	NPD4821	Approved
0.5955	Remote Similarity	NPD4819	Approved
0.5955	Remote Similarity	NPD7332	Phase 2
0.5952	Remote Similarity	NPD5276	Approved
0.5952	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD3194	Approved
0.5946	Remote Similarity	NPD3196	Approved
0.5946	Remote Similarity	NPD4266	Approved
0.5946	Remote Similarity	NPD3195	Phase 2
0.5934	Remote Similarity	NPD4788	Approved
0.5934	Remote Similarity	NPD7154	Phase 3
0.593	Remote Similarity	NPD8039	Approved
0.593	Remote Similarity	NPD6942	Approved
0.593	Remote Similarity	NPD7339	Approved
0.5926	Remote Similarity	NPD4632	Approved
0.5914	Remote Similarity	NPD4693	Phase 3
0.5914	Remote Similarity	NPD6684	Approved
0.5914	Remote Similarity	NPD5330	Approved
0.5914	Remote Similarity	NPD6409	Approved
0.5914	Remote Similarity	NPD7521	Approved
0.5914	Remote Similarity	NPD7146	Approved
0.5914	Remote Similarity	NPD4689	Approved
0.5914	Remote Similarity	NPD7334	Approved
0.5914	Remote Similarity	NPD4688	Approved
0.5914	Remote Similarity	NPD6422	Discontinued
0.5914	Remote Similarity	NPD5205	Approved
0.5914	Remote Similarity	NPD4690	Approved
0.5914	Remote Similarity	NPD4138	Approved
0.5909	Remote Similarity	NPD3617	Approved
0.5909	Remote Similarity	NPD3732	Approved
0.5905	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4225	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