NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	154.1
Volume:	167.971
LogP:	0.921
LogD:	-0.336
LogS:	-0.67
# Rotatable Bonds:	0
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	3.57
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.562
MDCK Permeability:	3.3359981898684055e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.864
Plasma Protein Binding (PPB):	44.61903381347656%
Volume Distribution (VD):	0.714
Pgp-substrate:	70.89179992675781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.595
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.726
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.742
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	10.192
Half-life (T1/2):	0.854

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.601
AMES Toxicity:	0.247
Rat Oral Acute Toxicity:	0.117
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.096
Carcinogencity:	0.189
Eye Corrosion:	0.676
Eye Irritation:	0.539
Respiratory Toxicity:	0.482

Download Data

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

Natural Product: NPC269985

Natural Product ID:	NPC269985
*Common Name:**	4-Hydroxy-3,5,5-Trimethylcyclohex-2-Enone
IUPAC Name:	4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	RLDREDRZMOWDOA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4,8,11H,5H2,1-3H3
SMILES:	O=C1C=C(C)C(C(C1)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463102
PubChem CID:	566734
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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9445	Crocus sativus	Species	Iridaceae	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
IC50	1
Others	3

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	1100000.0	nM	PMID[557113]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	13.3	%	PMID[557113]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	4.6	%	PMID[557113]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	1.6	%	PMID[557113]

☑ 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 NPC269985 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	145
0.1-0.2	1479
0.2-0.3	7911
0.3-0.4	17546
0.4-0.5	8183
0.5-0.6	5508
0.6-0.7	1683
0.7-0.8	214
0.8-0.85	15
0.85-0.9	6
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9254	High Similarity	NPC29542
0.9254	High Similarity	NPC201562
0.9254	High Similarity	NPC323437
0.8788	High Similarity	NPC106613
0.8696	High Similarity	NPC186042
0.8529	High Similarity	NPC136473
0.831	Intermediate Similarity	NPC215050
0.8308	Intermediate Similarity	NPC269737
0.8243	Intermediate Similarity	NPC19900
0.8169	Intermediate Similarity	NPC153660
0.8116	Intermediate Similarity	NPC117804
0.8108	Intermediate Similarity	NPC475994
0.8	Intermediate Similarity	NPC308038
0.7973	Intermediate Similarity	NPC82666
0.7973	Intermediate Similarity	NPC97173
0.7945	Intermediate Similarity	NPC166018
0.7945	Intermediate Similarity	NPC169056
0.7945	Intermediate Similarity	NPC225665
0.7922	Intermediate Similarity	NPC38796
0.7922	Intermediate Similarity	NPC158411
0.7895	Intermediate Similarity	NPC172013
0.7838	Intermediate Similarity	NPC263582
0.7812	Intermediate Similarity	NPC48891
0.7778	Intermediate Similarity	NPC95863
0.7763	Intermediate Similarity	NPC281138
0.7733	Intermediate Similarity	NPC471061
0.7733	Intermediate Similarity	NPC74995
0.7703	Intermediate Similarity	NPC114236
0.7692	Intermediate Similarity	NPC93590
0.7662	Intermediate Similarity	NPC157895
0.7662	Intermediate Similarity	NPC148685
0.7662	Intermediate Similarity	NPC160582
0.7662	Intermediate Similarity	NPC104120
0.7632	Intermediate Similarity	NPC62336
0.7606	Intermediate Similarity	NPC45264
0.7595	Intermediate Similarity	NPC169941
0.7595	Intermediate Similarity	NPC251475
0.7581	Intermediate Similarity	NPC64866
0.7571	Intermediate Similarity	NPC472072
0.7532	Intermediate Similarity	NPC152061
0.7531	Intermediate Similarity	NPC472974
0.7531	Intermediate Similarity	NPC472986
0.7531	Intermediate Similarity	NPC472985
0.75	Intermediate Similarity	NPC230527
0.75	Intermediate Similarity	NPC40687
0.75	Intermediate Similarity	NPC7927
0.75	Intermediate Similarity	NPC260573
0.75	Intermediate Similarity	NPC203403
0.75	Intermediate Similarity	NPC197659
0.75	Intermediate Similarity	NPC86917
0.7468	Intermediate Similarity	NPC279186
0.7467	Intermediate Similarity	NPC474011
0.7436	Intermediate Similarity	NPC45495
0.7436	Intermediate Similarity	NPC471514
0.7432	Intermediate Similarity	NPC247586
0.7424	Intermediate Similarity	NPC268185
0.7424	Intermediate Similarity	NPC71755
0.7407	Intermediate Similarity	NPC179006
0.7407	Intermediate Similarity	NPC474853
0.7407	Intermediate Similarity	NPC476426
0.7403	Intermediate Similarity	NPC231739
0.7403	Intermediate Similarity	NPC478122
0.7397	Intermediate Similarity	NPC107848
0.7385	Intermediate Similarity	NPC232247
0.7385	Intermediate Similarity	NPC251666
0.7381	Intermediate Similarity	NPC134321
0.7375	Intermediate Similarity	NPC105173
0.7368	Intermediate Similarity	NPC7629
0.7368	Intermediate Similarity	NPC469646
0.7368	Intermediate Similarity	NPC470525
0.7368	Intermediate Similarity	NPC151622
0.7361	Intermediate Similarity	NPC469679
0.7361	Intermediate Similarity	NPC469688
0.7344	Intermediate Similarity	NPC217188
0.7342	Intermediate Similarity	NPC474980
0.7342	Intermediate Similarity	NPC470298
0.7342	Intermediate Similarity	NPC6663
0.7317	Intermediate Similarity	NPC194417
0.7308	Intermediate Similarity	NPC7232
0.7297	Intermediate Similarity	NPC474884
0.7294	Intermediate Similarity	NPC475441
0.7294	Intermediate Similarity	NPC116726
0.7284	Intermediate Similarity	NPC31086
0.7284	Intermediate Similarity	NPC472326
0.7284	Intermediate Similarity	NPC219966
0.7284	Intermediate Similarity	NPC476412
0.7273	Intermediate Similarity	NPC34110
0.7262	Intermediate Similarity	NPC472983
0.7262	Intermediate Similarity	NPC472973
0.7231	Intermediate Similarity	NPC189677
0.7222	Intermediate Similarity	NPC96962
0.7215	Intermediate Similarity	NPC271104
0.72	Intermediate Similarity	NPC275098
0.7195	Intermediate Similarity	NPC52628
0.7195	Intermediate Similarity	NPC15807
0.7183	Intermediate Similarity	NPC474304
0.7183	Intermediate Similarity	NPC474329
0.7179	Intermediate Similarity	NPC297996
0.7176	Intermediate Similarity	NPC128672
0.7176	Intermediate Similarity	NPC48010
0.7162	Intermediate Similarity	NPC286154
0.7162	Intermediate Similarity	NPC203819
0.7162	Intermediate Similarity	NPC173321
0.716	Intermediate Similarity	NPC64600
0.7143	Intermediate Similarity	NPC250621
0.7143	Intermediate Similarity	NPC474854
0.7126	Intermediate Similarity	NPC78159
0.7126	Intermediate Similarity	NPC196227
0.7125	Intermediate Similarity	NPC226068
0.7125	Intermediate Similarity	NPC136150
0.7108	Intermediate Similarity	NPC470955
0.7108	Intermediate Similarity	NPC196381
0.7108	Intermediate Similarity	NPC198761
0.7105	Intermediate Similarity	NPC227814
0.7105	Intermediate Similarity	NPC144995
0.7093	Intermediate Similarity	NPC472978
0.7083	Intermediate Similarity	NPC166791
0.7083	Intermediate Similarity	NPC322035
0.7083	Intermediate Similarity	NPC100719
0.7083	Intermediate Similarity	NPC137163
0.7073	Intermediate Similarity	NPC470812
0.7073	Intermediate Similarity	NPC227132
0.7067	Intermediate Similarity	NPC319163
0.7067	Intermediate Similarity	NPC67076
0.7067	Intermediate Similarity	NPC84790
0.7059	Intermediate Similarity	NPC311852
0.7059	Intermediate Similarity	NPC473999
0.7059	Intermediate Similarity	NPC309603
0.7059	Intermediate Similarity	NPC123912
0.7059	Intermediate Similarity	NPC473100
0.7059	Intermediate Similarity	NPC214387
0.7051	Intermediate Similarity	NPC266193
0.7051	Intermediate Similarity	NPC97377
0.7051	Intermediate Similarity	NPC325946
0.7051	Intermediate Similarity	NPC257666
0.7045	Intermediate Similarity	NPC476245
0.7045	Intermediate Similarity	NPC271195
0.7042	Intermediate Similarity	NPC150162
0.7027	Intermediate Similarity	NPC10758
0.7027	Intermediate Similarity	NPC250928
0.7024	Intermediate Similarity	NPC287079
0.7024	Intermediate Similarity	NPC312561
0.7013	Intermediate Similarity	NPC474885
0.7011	Intermediate Similarity	NPC69454
0.7011	Intermediate Similarity	NPC472930
0.7	Intermediate Similarity	NPC470947
0.7	Intermediate Similarity	NPC470945
0.7	Intermediate Similarity	NPC470946
0.7	Intermediate Similarity	NPC472301
0.7	Intermediate Similarity	NPC74086
0.7	Intermediate Similarity	NPC2482
0.7	Intermediate Similarity	NPC207007
0.7	Intermediate Similarity	NPC306095
0.7	Intermediate Similarity	NPC321867
0.7	Intermediate Similarity	NPC68679
0.6988	Remote Similarity	NPC471224
0.6988	Remote Similarity	NPC32037
0.6988	Remote Similarity	NPC187529
0.6988	Remote Similarity	NPC474860
0.6988	Remote Similarity	NPC274724
0.6988	Remote Similarity	NPC470574
0.6988	Remote Similarity	NPC471300
0.6988	Remote Similarity	NPC474083
0.6988	Remote Similarity	NPC255174
0.6988	Remote Similarity	NPC70685
0.6986	Remote Similarity	NPC472875
0.6977	Remote Similarity	NPC230332
0.6977	Remote Similarity	NPC473455
0.6977	Remote Similarity	NPC473099
0.6977	Remote Similarity	NPC477147
0.6977	Remote Similarity	NPC477149
0.6974	Remote Similarity	NPC56747
0.6974	Remote Similarity	NPC180015
0.6974	Remote Similarity	NPC109576
0.6974	Remote Similarity	NPC130016
0.6974	Remote Similarity	NPC261316
0.6974	Remote Similarity	NPC49737
0.6966	Remote Similarity	NPC117133
0.6962	Remote Similarity	NPC275494
0.6962	Remote Similarity	NPC321180
0.6962	Remote Similarity	NPC471409
0.6962	Remote Similarity	NPC178852
0.6951	Remote Similarity	NPC41539
0.6951	Remote Similarity	NPC477784
0.6951	Remote Similarity	NPC62214
0.6951	Remote Similarity	NPC477785
0.6951	Remote Similarity	NPC477786
0.6941	Remote Similarity	NPC471791
0.6941	Remote Similarity	NPC53454
0.6941	Remote Similarity	NPC104560
0.6941	Remote Similarity	NPC472802
0.6941	Remote Similarity	NPC476796
0.6941	Remote Similarity	NPC471793
0.6932	Remote Similarity	NPC472976
0.6932	Remote Similarity	NPC472977
0.6923	Remote Similarity	NPC35756
0.6923	Remote Similarity	NPC472305
0.6923	Remote Similarity	NPC474197
0.6914	Remote Similarity	NPC121984
0.6914	Remote Similarity	NPC116797

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 NPC269985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	2054
0.2-0.3	4305
0.3-0.4	1972
0.4-0.5	405
0.5-0.6	230
0.6-0.7	42
0.7-0.8	5
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
0.7108	Intermediate Similarity	NPD3618	Phase 1
0.7	Intermediate Similarity	NPD368	Approved
0.7	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3133	Approved
0.6867	Remote Similarity	NPD3666	Approved
0.6867	Remote Similarity	NPD3665	Phase 1
0.6849	Remote Similarity	NPD7331	Phase 2
0.6812	Remote Similarity	NPD287	Approved
0.6786	Remote Similarity	NPD1696	Phase 3
0.675	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6110	Phase 1
0.6706	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5328	Approved
0.6627	Remote Similarity	NPD3667	Approved
0.6618	Remote Similarity	NPD342	Phase 1
0.6517	Remote Similarity	NPD7515	Phase 2
0.6517	Remote Similarity	NPD6079	Approved
0.6512	Remote Similarity	NPD4623	Approved
0.6512	Remote Similarity	NPD4519	Discontinued
0.6471	Remote Similarity	NPD4786	Approved
0.6444	Remote Similarity	NPD4202	Approved
0.6413	Remote Similarity	NPD4697	Phase 3
0.6404	Remote Similarity	NPD5785	Approved
0.6395	Remote Similarity	NPD5363	Approved
0.6395	Remote Similarity	NPD1694	Approved
0.6389	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4695	Discontinued
0.6386	Remote Similarity	NPD4252	Approved
0.6377	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD8264	Approved
0.6301	Remote Similarity	NPD4191	Approved
0.6301	Remote Similarity	NPD4194	Approved
0.6301	Remote Similarity	NPD4192	Approved
0.6301	Remote Similarity	NPD4193	Approved
0.6292	Remote Similarity	NPD4753	Phase 2
0.6286	Remote Similarity	NPD4219	Approved
0.6279	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD5211	Phase 2
0.6237	Remote Similarity	NPD5222	Approved
0.6237	Remote Similarity	NPD5221	Approved
0.6237	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4270	Approved
0.6235	Remote Similarity	NPD4269	Approved
0.6235	Remote Similarity	NPD4223	Phase 3
0.6235	Remote Similarity	NPD4221	Approved
0.622	Remote Similarity	NPD4756	Discovery
0.6216	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7748	Approved
0.6184	Remote Similarity	NPD3704	Approved
0.617	Remote Similarity	NPD7902	Approved
0.617	Remote Similarity	NPD5173	Approved
0.617	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD4137	Phase 3
0.6136	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4629	Approved
0.6129	Remote Similarity	NPD5210	Approved
0.6125	Remote Similarity	NPD4732	Discontinued
0.6122	Remote Similarity	NPD5141	Approved
0.6105	Remote Similarity	NPD4225	Approved
0.6092	Remote Similarity	NPD4197	Approved
0.6076	Remote Similarity	NPD4747	Approved
0.6076	Remote Similarity	NPD4691	Approved
0.6042	Remote Similarity	NPD4700	Approved
0.6042	Remote Similarity	NPD7639	Approved
0.6042	Remote Similarity	NPD7640	Approved
0.6042	Remote Similarity	NPD4696	Approved
0.6042	Remote Similarity	NPD5285	Approved
0.6042	Remote Similarity	NPD5286	Approved
0.6023	Remote Similarity	NPD5329	Approved
0.6	Remote Similarity	NPD4265	Approved
0.6	Remote Similarity	NPD5276	Approved
0.5979	Remote Similarity	NPD5223	Approved
0.5977	Remote Similarity	NPD7154	Phase 3
0.5977	Remote Similarity	NPD5362	Discontinued
0.5976	Remote Similarity	NPD8039	Approved
0.5957	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6409	Approved
0.5955	Remote Similarity	NPD5690	Phase 2
0.5955	Remote Similarity	NPD6684	Approved
0.5955	Remote Similarity	NPD4688	Approved
0.5955	Remote Similarity	NPD4689	Approved
0.5955	Remote Similarity	NPD5205	Approved
0.5955	Remote Similarity	NPD5280	Approved
0.5955	Remote Similarity	NPD4690	Approved
0.5955	Remote Similarity	NPD4138	Approved
0.5955	Remote Similarity	NPD5786	Approved
0.5955	Remote Similarity	NPD7146	Approved
0.5955	Remote Similarity	NPD5330	Approved
0.5955	Remote Similarity	NPD4693	Phase 3
0.5955	Remote Similarity	NPD4694	Approved
0.5955	Remote Similarity	NPD7334	Approved
0.5955	Remote Similarity	NPD7521	Approved
0.5952	Remote Similarity	NPD3617	Approved
0.5952	Remote Similarity	NPD4271	Approved
0.5952	Remote Similarity	NPD4268	Approved
0.5938	Remote Similarity	NPD7638	Approved
0.5918	Remote Similarity	NPD5226	Approved
0.5918	Remote Similarity	NPD4633	Approved
0.5918	Remote Similarity	NPD5224	Approved
0.5918	Remote Similarity	NPD5225	Approved
0.5914	Remote Similarity	NPD6399	Phase 3
0.5909	Remote Similarity	NPD3668	Phase 3
0.5897	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6698	Approved
0.587	Remote Similarity	NPD46	Approved
0.5862	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5209	Approved
0.5859	Remote Similarity	NPD5174	Approved
0.5859	Remote Similarity	NPD4754	Approved
0.5859	Remote Similarity	NPD5175	Approved
0.5854	Remote Similarity	NPD5733	Approved
0.5854	Remote Similarity	NPD4687	Approved
0.5854	Remote Similarity	NPD4058	Approved
0.5851	Remote Similarity	NPD5282	Discontinued
0.5851	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7900	Approved
0.5844	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD6084	Phase 2
0.5824	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6903	Approved
0.5814	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4822	Approved
0.5814	Remote Similarity	NPD4821	Approved
0.5814	Remote Similarity	NPD4820	Approved
0.5814	Remote Similarity	NPD4819	Approved
0.5806	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5281	Approved
0.5806	Remote Similarity	NPD5284	Approved
0.5795	Remote Similarity	NPD5332	Approved
0.5795	Remote Similarity	NPD5331	Approved
0.5794	Remote Similarity	NPD7115	Discovery
0.5789	Remote Similarity	NPD5695	Phase 3
0.5773	Remote Similarity	NPD5696	Approved
0.5769	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5370	Suspended
0.5747	Remote Similarity	NPD5369	Approved
0.5747	Remote Similarity	NPD4790	Discontinued
0.5745	Remote Similarity	NPD5779	Approved
0.5745	Remote Similarity	NPD5778	Approved
0.5743	Remote Similarity	NPD6675	Approved
0.5743	Remote Similarity	NPD4767	Approved
0.5743	Remote Similarity	NPD4768	Approved
0.5743	Remote Similarity	NPD5739	Approved
0.5743	Remote Similarity	NPD6402	Approved
0.5743	Remote Similarity	NPD7128	Approved
0.5728	Remote Similarity	NPD6372	Approved
0.5728	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3197	Phase 1
0.5699	Remote Similarity	NPD4096	Approved
0.5698	Remote Similarity	NPD7645	Phase 2
0.5698	Remote Similarity	NPD4195	Approved
0.5686	Remote Similarity	NPD5701	Approved
0.5686	Remote Similarity	NPD5697	Approved
0.5652	Remote Similarity	NPD5737	Approved
0.5652	Remote Similarity	NPD6672	Approved
0.5652	Remote Similarity	NPD4518	Approved
0.5647	Remote Similarity	NPD5776	Phase 2
0.5647	Remote Similarity	NPD6925	Approved
0.5638	Remote Similarity	NPD7637	Suspended
0.5638	Remote Similarity	NPD6411	Approved
0.5632	Remote Similarity	NPD7514	Phase 3
0.5632	Remote Similarity	NPD7332	Phase 2
0.5632	Remote Similarity	NPD5368	Approved
0.5631	Remote Similarity	NPD6899	Approved
0.5631	Remote Similarity	NPD6011	Approved
0.5631	Remote Similarity	NPD4729	Approved
0.5631	Remote Similarity	NPD4730	Approved
0.5631	Remote Similarity	NPD5128	Approved
0.5631	Remote Similarity	NPD6881	Approved
0.5631	Remote Similarity	NPD7320	Approved
0.5631	Remote Similarity	NPD5168	Approved
0.5625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6650	Approved
0.5619	Remote Similarity	NPD6649	Approved
0.5618	Remote Similarity	NPD4788	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