NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	186.13
Volume:	196.694
LogP:	0.26
LogD:	0.322
LogS:	-0.679
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	4.253
Fsp3:	0.8
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:	1.2556492947624065e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.856
Plasma Protein Binding (PPB):	43.855648040771484%
Volume Distribution (VD):	0.644
Pgp-substrate:	51.14348602294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.759
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.625
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	3.486
Half-life (T1/2):	0.715

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.28
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.096
Carcinogencity:	0.89
Eye Corrosion:	0.004
Eye Irritation:	0.287
Respiratory Toxicity:	0.219

Download Data

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

Natural Product: NPC82337

Natural Product ID:	NPC82337
*Common Name:**	Para-Menth-3-Ene-1,2,8-Triol
IUPAC Name:	(1S,2R)-4-(2-hydroxypropan-2-yl)-1-methylcyclohex-3-ene-1,2-diol
Synonyms:
Standard InCHIKey:	CYSRURFSGZEJNU-SCZZXKLOSA-N
Standard InCHI:	InChI=1S/C10H18O3/c1-9(2,12)7-4-5-10(3,13)8(11)6-7/h6,8,11-13H,4-5H2,1-3H3/t8-,10+/m1/s1
SMILES:	O[C@@H]1C=C(CC[C@]1(C)O)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011541
PubChem CID:	57404439
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001401] Menthane monoterpenoids

*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
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	roots	n.a.	n.a.	PMID[22381047]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6336	Asarum sieboldii	Species	Aristolochiaceae	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
EC50	4

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT106	Individual Protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	EC50	=	48500.0	nM	PMID[468450]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	21700.0	nM	PMID[468450]
NPT2	Others	Unspecified		EC50	=	4300.0	nM	PMID[468450]
NPT866	Individual Protein	Peroxisome proliferator-activated receptor alpha	Homo sapiens	EC50	=	19500.0	nM	PMID[468450]

☑ 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 NPC82337 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	158
0.1-0.2	1664
0.2-0.3	6291
0.3-0.4	17522
0.4-0.5	9952
0.5-0.6	5659
0.6-0.7	1221
0.7-0.8	202
0.8-0.85	19
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8923	High Similarity	NPC267027
0.8769	High Similarity	NPC471200
0.8636	High Similarity	NPC326310
0.8438	Intermediate Similarity	NPC66020
0.8438	Intermediate Similarity	NPC240506
0.8358	Intermediate Similarity	NPC311736
0.8235	Intermediate Similarity	NPC163290
0.8209	Intermediate Similarity	NPC287339
0.8182	Intermediate Similarity	NPC473508
0.8169	Intermediate Similarity	NPC220939
0.8169	Intermediate Similarity	NPC265485
0.8108	Intermediate Similarity	NPC13823
0.8108	Intermediate Similarity	NPC68119
0.8088	Intermediate Similarity	NPC202017
0.803	Intermediate Similarity	NPC207007
0.803	Intermediate Similarity	NPC68679
0.803	Intermediate Similarity	NPC321867
0.8028	Intermediate Similarity	NPC23954
0.8028	Intermediate Similarity	NPC242992
0.8	Intermediate Similarity	NPC122239
0.8	Intermediate Similarity	NPC473893
0.7971	Intermediate Similarity	NPC73603
0.7937	Intermediate Similarity	NPC227135
0.7937	Intermediate Similarity	NPC130209
0.7937	Intermediate Similarity	NPC148216
0.7937	Intermediate Similarity	NPC148163
0.791	Intermediate Similarity	NPC83200
0.7867	Intermediate Similarity	NPC83351
0.7867	Intermediate Similarity	NPC167891
0.7857	Intermediate Similarity	NPC96484
0.7857	Intermediate Similarity	NPC305698
0.7838	Intermediate Similarity	NPC236228
0.7838	Intermediate Similarity	NPC256720
0.7838	Intermediate Similarity	NPC170148
0.7808	Intermediate Similarity	NPC190859
0.7794	Intermediate Similarity	NPC300593
0.7778	Intermediate Similarity	NPC469343
0.775	Intermediate Similarity	NPC255143
0.7746	Intermediate Similarity	NPC471560
0.7733	Intermediate Similarity	NPC40049
0.7722	Intermediate Similarity	NPC83702
0.7714	Intermediate Similarity	NPC259299
0.7714	Intermediate Similarity	NPC114651
0.7662	Intermediate Similarity	NPC236707
0.7656	Intermediate Similarity	NPC251666
0.7656	Intermediate Similarity	NPC232247
0.7639	Intermediate Similarity	NPC34834
0.7632	Intermediate Similarity	NPC475980
0.7612	Intermediate Similarity	NPC99487
0.76	Intermediate Similarity	NPC253190
0.76	Intermediate Similarity	NPC126969
0.76	Intermediate Similarity	NPC265588
0.7595	Intermediate Similarity	NPC474634
0.7576	Intermediate Similarity	NPC155025
0.7576	Intermediate Similarity	NPC226848
0.7568	Intermediate Similarity	NPC306727
0.7564	Intermediate Similarity	NPC23852
0.7564	Intermediate Similarity	NPC476646
0.7564	Intermediate Similarity	NPC471270
0.7564	Intermediate Similarity	NPC209620
0.7561	Intermediate Similarity	NPC474668
0.7538	Intermediate Similarity	NPC48891
0.7538	Intermediate Similarity	NPC24443
0.7536	Intermediate Similarity	NPC96793
0.7536	Intermediate Similarity	NPC323424
0.7534	Intermediate Similarity	NPC471271
0.7534	Intermediate Similarity	NPC477792
0.7534	Intermediate Similarity	NPC471268
0.75	Intermediate Similarity	NPC74722
0.75	Intermediate Similarity	NPC474248
0.75	Intermediate Similarity	NPC475251
0.75	Intermediate Similarity	NPC477426
0.75	Intermediate Similarity	NPC16964
0.75	Intermediate Similarity	NPC477425
0.75	Intermediate Similarity	NPC477427
0.75	Intermediate Similarity	NPC304690
0.75	Intermediate Similarity	NPC476703
0.75	Intermediate Similarity	NPC474826
0.747	Intermediate Similarity	NPC49783
0.747	Intermediate Similarity	NPC470361
0.7468	Intermediate Similarity	NPC50964
0.7468	Intermediate Similarity	NPC471408
0.7467	Intermediate Similarity	NPC23231
0.7467	Intermediate Similarity	NPC32832
0.7467	Intermediate Similarity	NPC60818
0.7463	Intermediate Similarity	NPC475931
0.7436	Intermediate Similarity	NPC95124
0.7436	Intermediate Similarity	NPC96362
0.7436	Intermediate Similarity	NPC471266
0.7432	Intermediate Similarity	NPC130665
0.7429	Intermediate Similarity	NPC473722
0.7429	Intermediate Similarity	NPC308844
0.7424	Intermediate Similarity	NPC52012
0.7403	Intermediate Similarity	NPC477089
0.7397	Intermediate Similarity	NPC129630
0.7397	Intermediate Similarity	NPC92801
0.7397	Intermediate Similarity	NPC471781
0.7391	Intermediate Similarity	NPC174956
0.7385	Intermediate Similarity	NPC281590
0.7381	Intermediate Similarity	NPC291484
0.7381	Intermediate Similarity	NPC80561
0.7381	Intermediate Similarity	NPC329596
0.7381	Intermediate Similarity	NPC3345
0.7381	Intermediate Similarity	NPC204188
0.7381	Intermediate Similarity	NPC11216
0.7375	Intermediate Similarity	NPC185605
0.7375	Intermediate Similarity	NPC317458
0.7361	Intermediate Similarity	NPC245795
0.7361	Intermediate Similarity	NPC208999
0.7361	Intermediate Similarity	NPC224532
0.7361	Intermediate Similarity	NPC471238
0.7349	Intermediate Similarity	NPC133588
0.7342	Intermediate Similarity	NPC470298
0.7342	Intermediate Similarity	NPC264245
0.7342	Intermediate Similarity	NPC249423
0.7333	Intermediate Similarity	NPC471525
0.7333	Intermediate Similarity	NPC24590
0.7333	Intermediate Similarity	NPC476366
0.7333	Intermediate Similarity	NPC201048
0.7317	Intermediate Similarity	NPC6391
0.7317	Intermediate Similarity	NPC293287
0.7317	Intermediate Similarity	NPC261266
0.7317	Intermediate Similarity	NPC281316
0.7317	Intermediate Similarity	NPC152808
0.7308	Intermediate Similarity	NPC328714
0.7308	Intermediate Similarity	NPC28862
0.7308	Intermediate Similarity	NPC47982
0.7308	Intermediate Similarity	NPC109546
0.7308	Intermediate Similarity	NPC476701
0.7308	Intermediate Similarity	NPC143182
0.7308	Intermediate Similarity	NPC81306
0.7308	Intermediate Similarity	NPC84694
0.7302	Intermediate Similarity	NPC244038
0.7297	Intermediate Similarity	NPC471272
0.7297	Intermediate Similarity	NPC164022
0.7294	Intermediate Similarity	NPC97404
0.7294	Intermediate Similarity	NPC116726
0.7294	Intermediate Similarity	NPC41554
0.7286	Intermediate Similarity	NPC290367
0.7286	Intermediate Similarity	NPC110241
0.7286	Intermediate Similarity	NPC107540
0.7284	Intermediate Similarity	NPC185568
0.7273	Intermediate Similarity	NPC471061
0.7273	Intermediate Similarity	NPC470711
0.7273	Intermediate Similarity	NPC91594
0.7273	Intermediate Similarity	NPC470758
0.7273	Intermediate Similarity	NPC471798
0.7273	Intermediate Similarity	NPC130136
0.7262	Intermediate Similarity	NPC115607
0.726	Intermediate Similarity	NPC472947
0.726	Intermediate Similarity	NPC217570
0.726	Intermediate Similarity	NPC239373
0.726	Intermediate Similarity	NPC329989
0.726	Intermediate Similarity	NPC90115
0.725	Intermediate Similarity	NPC477390
0.725	Intermediate Similarity	NPC49964
0.725	Intermediate Similarity	NPC477385
0.725	Intermediate Similarity	NPC472465
0.7246	Intermediate Similarity	NPC225342
0.7237	Intermediate Similarity	NPC477923
0.7237	Intermediate Similarity	NPC12696
0.7237	Intermediate Similarity	NPC66566
0.7229	Intermediate Similarity	NPC476948
0.7222	Intermediate Similarity	NPC136813
0.7222	Intermediate Similarity	NPC171225
0.7222	Intermediate Similarity	NPC96962
0.7222	Intermediate Similarity	NPC477791
0.7215	Intermediate Similarity	NPC113024
0.7215	Intermediate Similarity	NPC470946
0.7215	Intermediate Similarity	NPC470947
0.7215	Intermediate Similarity	NPC470945
0.7215	Intermediate Similarity	NPC474592
0.7215	Intermediate Similarity	NPC234193
0.7215	Intermediate Similarity	NPC287749
0.7215	Intermediate Similarity	NPC241290
0.7215	Intermediate Similarity	NPC209944
0.7215	Intermediate Similarity	NPC164840
0.7209	Intermediate Similarity	NPC310013
0.72	Intermediate Similarity	NPC95165
0.72	Intermediate Similarity	NPC471799
0.72	Intermediate Similarity	NPC476709
0.7195	Intermediate Similarity	NPC187529
0.7195	Intermediate Similarity	NPC298595
0.7188	Intermediate Similarity	NPC179169
0.7188	Intermediate Similarity	NPC71506
0.7188	Intermediate Similarity	NPC177112
0.7188	Intermediate Similarity	NPC35519
0.7188	Intermediate Similarity	NPC306195
0.7188	Intermediate Similarity	NPC157781
0.7188	Intermediate Similarity	NPC181255
0.7183	Intermediate Similarity	NPC250836
0.7183	Intermediate Similarity	NPC61503
0.7179	Intermediate Similarity	NPC474216
0.7179	Intermediate Similarity	NPC137345
0.7179	Intermediate Similarity	NPC87604
0.7179	Intermediate Similarity	NPC476314
0.7179	Intermediate Similarity	NPC181838
0.7176	Intermediate Similarity	NPC473099
0.7176	Intermediate Similarity	NPC191323
0.7162	Intermediate Similarity	NPC470041

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 NPC82337 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	2242
0.2-0.3	3897
0.3-0.4	2077
0.4-0.5	615
0.5-0.6	119
0.6-0.7	40
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.803	Intermediate Similarity	NPD368	Approved
0.7937	Intermediate Similarity	NPD342	Phase 1
0.7229	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD8264	Approved
0.7	Intermediate Similarity	NPD6930	Phase 2
0.7	Intermediate Similarity	NPD6931	Approved
0.6974	Remote Similarity	NPD4732	Discontinued
0.6923	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6933	Approved
0.6875	Remote Similarity	NPD6929	Approved
0.6824	Remote Similarity	NPD7524	Approved
0.6795	Remote Similarity	NPD7339	Approved
0.6795	Remote Similarity	NPD6942	Approved
0.679	Remote Similarity	NPD7514	Phase 3
0.679	Remote Similarity	NPD7332	Phase 2
0.6747	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5776	Phase 2
0.6625	Remote Similarity	NPD6925	Approved
0.6588	Remote Similarity	NPD6893	Approved
0.6543	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7145	Approved
0.6522	Remote Similarity	NPD4219	Approved
0.6506	Remote Similarity	NPD6902	Approved
0.6506	Remote Similarity	NPD6898	Phase 1
0.6463	Remote Similarity	NPD7645	Phase 2
0.6437	Remote Similarity	NPD7750	Discontinued
0.6429	Remote Similarity	NPD3667	Approved
0.642	Remote Similarity	NPD6932	Approved
0.6395	Remote Similarity	NPD1696	Phase 3
0.6386	Remote Similarity	NPD7525	Registered
0.6316	Remote Similarity	NPD5344	Discontinued
0.6279	Remote Similarity	NPD4786	Approved
0.6265	Remote Similarity	NPD6683	Phase 2
0.6264	Remote Similarity	NPD5778	Approved
0.6264	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD4265	Approved
0.6222	Remote Similarity	NPD7838	Discovery
0.6222	Remote Similarity	NPD6698	Approved
0.6222	Remote Similarity	NPD46	Approved
0.6203	Remote Similarity	NPD7150	Approved
0.6203	Remote Similarity	NPD7152	Approved
0.6203	Remote Similarity	NPD7151	Approved
0.619	Remote Similarity	NPD7509	Discontinued
0.619	Remote Similarity	NPD4822	Approved
0.619	Remote Similarity	NPD4819	Approved
0.619	Remote Similarity	NPD4748	Discontinued
0.619	Remote Similarity	NPD4820	Approved
0.619	Remote Similarity	NPD4821	Approved
0.6184	Remote Similarity	NPD7331	Phase 2
0.6164	Remote Similarity	NPD1145	Discontinued
0.6163	Remote Similarity	NPD6110	Phase 1
0.6154	Remote Similarity	NPD7983	Approved
0.6154	Remote Similarity	NPD7087	Discontinued
0.6154	Remote Similarity	NPD6923	Approved
0.6154	Remote Similarity	NPD6922	Approved
0.6076	Remote Similarity	NPD7144	Approved
0.6076	Remote Similarity	NPD7143	Approved
0.6053	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4785	Approved
0.6049	Remote Similarity	NPD4784	Approved
0.6	Remote Similarity	NPD388	Approved
0.6	Remote Similarity	NPD386	Approved
0.6	Remote Similarity	NPD4243	Approved
0.5977	Remote Similarity	NPD5331	Approved
0.5977	Remote Similarity	NPD7154	Phase 3
0.5977	Remote Similarity	NPD5332	Approved
0.5977	Remote Similarity	NPD5362	Discontinued
0.5955	Remote Similarity	NPD3618	Phase 1
0.5952	Remote Similarity	NPD4271	Approved
0.5952	Remote Similarity	NPD4268	Approved
0.5938	Remote Similarity	NPD4225	Approved
0.5938	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.593	Remote Similarity	NPD4790	Discontinued
0.5921	Remote Similarity	NPD371	Approved
0.5909	Remote Similarity	NPD3665	Phase 1
0.5909	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD3133	Approved
0.5909	Remote Similarity	NPD3666	Approved
0.5876	Remote Similarity	NPD6648	Approved
0.5876	Remote Similarity	NPD7639	Approved
0.5876	Remote Similarity	NPD7640	Approved
0.587	Remote Similarity	NPD3168	Discontinued
0.5862	Remote Similarity	NPD4269	Approved
0.5862	Remote Similarity	NPD4270	Approved
0.5844	Remote Similarity	NPD7341	Phase 2
0.5814	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7637	Suspended
0.5783	Remote Similarity	NPD4190	Phase 3
0.5783	Remote Similarity	NPD5275	Approved
0.5778	Remote Similarity	NPD4519	Discontinued
0.5778	Remote Similarity	NPD4249	Approved
0.5778	Remote Similarity	NPD4623	Approved
0.5773	Remote Similarity	NPD7638	Approved
0.5765	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5328	Approved
0.575	Remote Similarity	NPD15	Approved
0.575	Remote Similarity	NPD791	Approved
0.5745	Remote Similarity	NPD4202	Approved
0.5733	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.573	Remote Similarity	NPD3668	Phase 3
0.5729	Remote Similarity	NPD7839	Suspended
0.5714	Remote Similarity	NPD3197	Phase 1
0.5714	Remote Similarity	NPD4251	Approved
0.5714	Remote Similarity	NPD4250	Approved
0.5699	Remote Similarity	NPD7136	Phase 2
0.5698	Remote Similarity	NPD4195	Approved
0.5696	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD385	Approved
0.5672	Remote Similarity	NPD384	Approved
0.5667	Remote Similarity	NPD5363	Approved
0.5658	Remote Similarity	NPD4191	Approved
0.5658	Remote Similarity	NPD4193	Approved
0.5658	Remote Similarity	NPD4192	Approved
0.5658	Remote Similarity	NPD4194	Approved
0.5657	Remote Similarity	NPD4159	Approved
0.5638	Remote Similarity	NPD7515	Phase 2
0.5638	Remote Similarity	NPD6079	Approved
0.5632	Remote Similarity	NPD4252	Approved
0.5619	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD5279	Phase 3
0.5604	Remote Similarity	NPD5786	Approved
0.56	Remote Similarity	NPD5211	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