NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	170.13
Volume:	187.904
LogP:	1.519
LogD:	1.556
LogS:	-0.875
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	3.435
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:	-4.269
MDCK Permeability:	3.333501081215218e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.699
Plasma Protein Binding (PPB):	47.24066162109375%
Volume Distribution (VD):	0.793
Pgp-substrate:	54.103118896484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.207
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.279
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.176

ADMET: Excretion

Clearance (CL):	8.33
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.131
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.679
Skin Sensitization:	0.754
Carcinogencity:	0.897
Eye Corrosion:	0.221
Eye Irritation:	0.98
Respiratory Toxicity:	0.306

Download Data

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

Natural Product: NPC66020

Natural Product ID:	NPC66020
*Common Name:**	(-)-1-P-Menthene-7,8-Diol
IUPAC Name:	2-[(1S)-4-(hydroxymethyl)cyclohex-3-en-1-yl]propan-2-ol
Synonyms:
Standard InCHIKey:	XYKGEKWHBMLSGS-SECBINFHSA-N
Standard InCHI:	InChI=1S/C10H18O2/c1-10(2,12)9-5-3-8(7-11)4-6-9/h3,9,11-12H,4-7H2,1-2H3/t9-/m1/s1
SMILES:	CC(C)([C@@H]1CC=C(CC1)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448219
PubChem CID:	44566704
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
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO7630	Cyperus longus	Species	Cyperaceae	Eukaryota	n.a.	Egyptian herbal medicine	n.a.	PMID[15104485]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7630	Cyperus longus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	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	2
Others	4

Activity Type	# Activity
Cell Line	5
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell Line	Hepatocyte	Mus musculus	IC50	=	90000.0	nM	PMID[533263]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	53.3	%	PMID[533263]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	16.7	%	PMID[533263]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	1.7	%	PMID[533263]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	-1.5	%	PMID[533263]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	1900.0	nM	PMID[533264]

☑ 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 NPC66020 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	1683
0.2-0.3	9796
0.3-0.4	16309
0.4-0.5	8531
0.5-0.6	4765
0.6-0.7	1204
0.7-0.8	212
0.8-0.85	39
0.85-0.9	6
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9153	High Similarity	NPC321867
0.9153	High Similarity	NPC207007
0.9153	High Similarity	NPC68679
0.9107	High Similarity	NPC130209
0.9107	High Similarity	NPC148163
0.9107	High Similarity	NPC148216
0.8983	High Similarity	NPC240506
0.8871	High Similarity	NPC267027
0.8571	High Similarity	NPC202017
0.8571	High Similarity	NPC326310
0.8548	High Similarity	NPC300593
0.8548	High Similarity	NPC107540
0.85	High Similarity	NPC475931
0.8485	Intermediate Similarity	NPC23954
0.8462	Intermediate Similarity	NPC471560
0.8448	Intermediate Similarity	NPC232247
0.8448	Intermediate Similarity	NPC251666
0.8438	Intermediate Similarity	NPC82337
0.8413	Intermediate Similarity	NPC471200
0.8393	Intermediate Similarity	NPC26906
0.8393	Intermediate Similarity	NPC214584
0.8387	Intermediate Similarity	NPC174956
0.8361	Intermediate Similarity	NPC99487
0.8358	Intermediate Similarity	NPC220939
0.8358	Intermediate Similarity	NPC265485
0.8333	Intermediate Similarity	NPC155025
0.8333	Intermediate Similarity	NPC34834
0.8308	Intermediate Similarity	NPC96484
0.8246	Intermediate Similarity	NPC181255
0.8246	Intermediate Similarity	NPC157781
0.8246	Intermediate Similarity	NPC35519
0.8246	Intermediate Similarity	NPC306195
0.8246	Intermediate Similarity	NPC179169
0.8197	Intermediate Similarity	NPC122239
0.8182	Intermediate Similarity	NPC474248
0.8182	Intermediate Similarity	NPC473893
0.8154	Intermediate Similarity	NPC114651
0.8154	Intermediate Similarity	NPC171225
0.8154	Intermediate Similarity	NPC136813
0.8095	Intermediate Similarity	NPC473508
0.8088	Intermediate Similarity	NPC130665
0.807	Intermediate Similarity	NPC244038
0.8033	Intermediate Similarity	NPC181872
0.8033	Intermediate Similarity	NPC226848
0.8	Intermediate Similarity	NPC48891
0.7971	Intermediate Similarity	NPC476366
0.7971	Intermediate Similarity	NPC201048
0.7969	Intermediate Similarity	NPC96793
0.7969	Intermediate Similarity	NPC323424
0.7937	Intermediate Similarity	NPC225342
0.7931	Intermediate Similarity	NPC71506
0.7931	Intermediate Similarity	NPC40417
0.7931	Intermediate Similarity	NPC294358
0.7931	Intermediate Similarity	NPC177112
0.7887	Intermediate Similarity	NPC474826
0.7887	Intermediate Similarity	NPC477426
0.7887	Intermediate Similarity	NPC477427
0.7887	Intermediate Similarity	NPC40049
0.7887	Intermediate Similarity	NPC477425
0.7879	Intermediate Similarity	NPC73603
0.7879	Intermediate Similarity	NPC68703
0.7879	Intermediate Similarity	NPC477791
0.7879	Intermediate Similarity	NPC69649
0.7857	Intermediate Similarity	NPC32832
0.7846	Intermediate Similarity	NPC308844
0.7833	Intermediate Similarity	NPC227135
0.7812	Intermediate Similarity	NPC81615
0.7812	Intermediate Similarity	NPC474155
0.7812	Intermediate Similarity	NPC473759
0.7761	Intermediate Similarity	NPC224532
0.7761	Intermediate Similarity	NPC167527
0.7761	Intermediate Similarity	NPC471238
0.7746	Intermediate Similarity	NPC265588
0.7746	Intermediate Similarity	NPC470749
0.7727	Intermediate Similarity	NPC311736
0.7727	Intermediate Similarity	NPC279434
0.7692	Intermediate Similarity	NPC309300
0.7681	Intermediate Similarity	NPC164022
0.7681	Intermediate Similarity	NPC242992
0.7681	Intermediate Similarity	NPC477792
0.7681	Intermediate Similarity	NPC471272
0.7656	Intermediate Similarity	NPC282694
0.7656	Intermediate Similarity	NPC194208
0.7656	Intermediate Similarity	NPC475251
0.7656	Intermediate Similarity	NPC79576
0.7647	Intermediate Similarity	NPC329989
0.7647	Intermediate Similarity	NPC239373
0.7639	Intermediate Similarity	NPC470758
0.7639	Intermediate Similarity	NPC91594
0.7639	Intermediate Similarity	NPC470711
0.7627	Intermediate Similarity	NPC68014
0.7612	Intermediate Similarity	NPC163290
0.7612	Intermediate Similarity	NPC259299
0.7606	Intermediate Similarity	NPC133580
0.7586	Intermediate Similarity	NPC329773
0.7576	Intermediate Similarity	NPC19569
0.7576	Intermediate Similarity	NPC258595
0.7571	Intermediate Similarity	NPC329763
0.7571	Intermediate Similarity	NPC234527
0.7571	Intermediate Similarity	NPC14352
0.7538	Intermediate Similarity	NPC83200
0.7536	Intermediate Similarity	NPC92801
0.7534	Intermediate Similarity	NPC167891
0.7534	Intermediate Similarity	NPC83351
0.75	Intermediate Similarity	NPC208999
0.75	Intermediate Similarity	NPC24824
0.75	Intermediate Similarity	NPC165651
0.75	Intermediate Similarity	NPC210560
0.75	Intermediate Similarity	NPC135648
0.75	Intermediate Similarity	NPC305698
0.75	Intermediate Similarity	NPC247325
0.75	Intermediate Similarity	NPC253190
0.75	Intermediate Similarity	NPC117804
0.75	Intermediate Similarity	NPC474496
0.75	Intermediate Similarity	NPC244488
0.7467	Intermediate Similarity	NPC264245
0.7465	Intermediate Similarity	NPC306727
0.7465	Intermediate Similarity	NPC190859
0.7465	Intermediate Similarity	NPC471659
0.7465	Intermediate Similarity	NPC309178
0.7463	Intermediate Similarity	NPC162309
0.7463	Intermediate Similarity	NPC476406
0.7432	Intermediate Similarity	NPC143182
0.7432	Intermediate Similarity	NPC81306
0.7432	Intermediate Similarity	NPC30986
0.7432	Intermediate Similarity	NPC28862
0.7432	Intermediate Similarity	NPC47982
0.7432	Intermediate Similarity	NPC209430
0.7432	Intermediate Similarity	NPC109546
0.7432	Intermediate Similarity	NPC84694
0.7429	Intermediate Similarity	NPC167706
0.7429	Intermediate Similarity	NPC471268
0.7429	Intermediate Similarity	NPC471271
0.7429	Intermediate Similarity	NPC471662
0.7424	Intermediate Similarity	NPC290367
0.7424	Intermediate Similarity	NPC225415
0.7419	Intermediate Similarity	NPC179024
0.7419	Intermediate Similarity	NPC24443
0.7397	Intermediate Similarity	NPC74995
0.7391	Intermediate Similarity	NPC90115
0.7391	Intermediate Similarity	NPC217570
0.7391	Intermediate Similarity	NPC74722
0.7391	Intermediate Similarity	NPC304690
0.7385	Intermediate Similarity	NPC210346
0.7368	Intermediate Similarity	NPC49964
0.7368	Intermediate Similarity	NPC87489
0.7361	Intermediate Similarity	NPC313185
0.7361	Intermediate Similarity	NPC60818
0.7361	Intermediate Similarity	NPC23231
0.7353	Intermediate Similarity	NPC472875
0.7353	Intermediate Similarity	NPC472253
0.7353	Intermediate Similarity	NPC197805
0.7353	Intermediate Similarity	NPC472255
0.7333	Intermediate Similarity	NPC164840
0.7333	Intermediate Similarity	NPC209944
0.7333	Intermediate Similarity	NPC271104
0.7333	Intermediate Similarity	NPC295131
0.7333	Intermediate Similarity	NPC234193
0.7333	Intermediate Similarity	NPC241290
0.7333	Intermediate Similarity	NPC472301
0.7324	Intermediate Similarity	NPC259049
0.7324	Intermediate Similarity	NPC186042
0.7324	Intermediate Similarity	NPC471799
0.7324	Intermediate Similarity	NPC474140
0.7324	Intermediate Similarity	NPC474743
0.7313	Intermediate Similarity	NPC287339
0.7313	Intermediate Similarity	NPC61503
0.7302	Intermediate Similarity	NPC52012
0.7302	Intermediate Similarity	NPC278550
0.7297	Intermediate Similarity	NPC474216
0.7297	Intermediate Similarity	NPC476314
0.7297	Intermediate Similarity	NPC297996
0.7297	Intermediate Similarity	NPC478122
0.7297	Intermediate Similarity	NPC470944
0.7288	Intermediate Similarity	NPC26960
0.7288	Intermediate Similarity	NPC474460
0.7288	Intermediate Similarity	NPC182102
0.7273	Intermediate Similarity	NPC475789
0.7273	Intermediate Similarity	NPC211291
0.7273	Intermediate Similarity	NPC474634
0.7273	Intermediate Similarity	NPC133368
0.726	Intermediate Similarity	NPC126969
0.726	Intermediate Similarity	NPC263582
0.726	Intermediate Similarity	NPC170148
0.726	Intermediate Similarity	NPC472305
0.726	Intermediate Similarity	NPC471658
0.726	Intermediate Similarity	NPC310643
0.7258	Intermediate Similarity	NPC67508
0.7258	Intermediate Similarity	NPC84824
0.7258	Intermediate Similarity	NPC329686
0.7258	Intermediate Similarity	NPC281590
0.7258	Intermediate Similarity	NPC298299
0.7246	Intermediate Similarity	NPC216460
0.7246	Intermediate Similarity	NPC245795
0.7246	Intermediate Similarity	NPC276616
0.7246	Intermediate Similarity	NPC266578
0.7237	Intermediate Similarity	NPC47761
0.7237	Intermediate Similarity	NPC249423
0.7237	Intermediate Similarity	NPC476646
0.7237	Intermediate Similarity	NPC209620

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 NPC66020 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	2314
0.2-0.3	4093
0.3-0.4	1904
0.4-0.5	497
0.5-0.6	163
0.6-0.7	37
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9153	High Similarity	NPD368	Approved
0.9107	High Similarity	NPD342	Phase 1
0.7123	Intermediate Similarity	NPD8264	Approved
0.7027	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6924	Approved
0.6986	Remote Similarity	NPD6926	Approved
0.6914	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4265	Approved
0.6892	Remote Similarity	NPD7339	Approved
0.6892	Remote Similarity	NPD6942	Approved
0.6883	Remote Similarity	NPD6930	Phase 2
0.6883	Remote Similarity	NPD6931	Approved
0.6875	Remote Similarity	NPD4219	Approved
0.6842	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6933	Approved
0.6753	Remote Similarity	NPD6929	Approved
0.6753	Remote Similarity	NPD7645	Phase 2
0.6712	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD7332	Phase 2
0.6625	Remote Similarity	NPD6695	Phase 3
0.6622	Remote Similarity	NPD4732	Discontinued
0.6543	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4784	Approved
0.6533	Remote Similarity	NPD4785	Approved
0.65	Remote Similarity	NPD3667	Approved
0.6494	Remote Similarity	NPD6925	Approved
0.6494	Remote Similarity	NPD5776	Phase 2
0.6479	Remote Similarity	NPD7331	Phase 2
0.6463	Remote Similarity	NPD6893	Approved
0.6463	Remote Similarity	NPD1696	Phase 3
0.6456	Remote Similarity	NPD4822	Approved
0.6456	Remote Similarity	NPD4821	Approved
0.6456	Remote Similarity	NPD7509	Discontinued
0.6456	Remote Similarity	NPD4819	Approved
0.6456	Remote Similarity	NPD4820	Approved
0.6447	Remote Similarity	NPD4190	Phase 3
0.6447	Remote Similarity	NPD5275	Approved
0.6438	Remote Similarity	NPD6923	Approved
0.6438	Remote Similarity	NPD6922	Approved
0.641	Remote Similarity	NPD7145	Approved
0.6386	Remote Similarity	NPD4623	Approved
0.6386	Remote Similarity	NPD4519	Discontinued
0.6375	Remote Similarity	NPD6902	Approved
0.6375	Remote Similarity	NPD6898	Phase 1
0.6351	Remote Similarity	NPD7143	Approved
0.6351	Remote Similarity	NPD7144	Approved
0.6341	Remote Similarity	NPD3133	Approved
0.6341	Remote Similarity	NPD4786	Approved
0.6341	Remote Similarity	NPD3666	Approved
0.6341	Remote Similarity	NPD3665	Phase 1
0.6338	Remote Similarity	NPD7341	Phase 2
0.6329	Remote Similarity	NPD4195	Approved
0.631	Remote Similarity	NPD7524	Approved
0.631	Remote Similarity	NPD7750	Discontinued
0.6282	Remote Similarity	NPD6932	Approved
0.6267	Remote Similarity	NPD7150	Approved
0.6267	Remote Similarity	NPD7151	Approved
0.6267	Remote Similarity	NPD7152	Approved
0.625	Remote Similarity	NPD4748	Discontinued
0.6232	Remote Similarity	NPD1145	Discontinued
0.623	Remote Similarity	NPD384	Approved
0.623	Remote Similarity	NPD385	Approved
0.622	Remote Similarity	NPD5332	Approved
0.622	Remote Similarity	NPD5331	Approved
0.622	Remote Similarity	NPD5362	Discontinued
0.6203	Remote Similarity	NPD4268	Approved
0.6203	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4271	Approved
0.619	Remote Similarity	NPD3618	Phase 1
0.6173	Remote Similarity	NPD4790	Discontinued
0.6163	Remote Similarity	NPD4753	Phase 2
0.6136	Remote Similarity	NPD5779	Approved
0.6136	Remote Similarity	NPD5778	Approved
0.6125	Remote Similarity	NPD6683	Phase 2
0.6111	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD4270	Approved
0.6098	Remote Similarity	NPD4221	Approved
0.6098	Remote Similarity	NPD4223	Phase 3
0.6098	Remote Similarity	NPD4269	Approved
0.6071	Remote Similarity	NPD319	Phase 1
0.6066	Remote Similarity	NPD388	Approved
0.6066	Remote Similarity	NPD386	Approved
0.6049	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD7154	Phase 3
0.6024	Remote Similarity	NPD6110	Phase 1
0.6023	Remote Similarity	NPD7087	Discontinued
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD5328	Approved
0.5955	Remote Similarity	NPD4202	Approved
0.5952	Remote Similarity	NPD4197	Approved
0.5915	Remote Similarity	NPD4194	Approved
0.5915	Remote Similarity	NPD4192	Approved
0.5915	Remote Similarity	NPD4193	Approved
0.5915	Remote Similarity	NPD4191	Approved
0.5882	Remote Similarity	NPD5329	Approved
0.5882	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5363	Approved
0.5854	Remote Similarity	NPD4252	Approved
0.5854	Remote Similarity	NPD4695	Discontinued
0.5843	Remote Similarity	NPD6079	Approved
0.5843	Remote Similarity	NPD7515	Phase 2
0.5824	Remote Similarity	NPD4629	Approved
0.5824	Remote Similarity	NPD5210	Approved
0.5814	Remote Similarity	NPD4688	Approved
0.5814	Remote Similarity	NPD5690	Phase 2
0.5814	Remote Similarity	NPD5280	Approved
0.5814	Remote Similarity	NPD4690	Approved
0.5814	Remote Similarity	NPD4138	Approved
0.5814	Remote Similarity	NPD5205	Approved
0.5814	Remote Similarity	NPD5786	Approved
0.5814	Remote Similarity	NPD4693	Phase 3
0.5814	Remote Similarity	NPD4689	Approved
0.5814	Remote Similarity	NPD4694	Approved
0.5795	Remote Similarity	NPD6051	Approved
0.5795	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD6101	Approved
0.5789	Remote Similarity	NPD5211	Phase 2
0.5789	Remote Similarity	NPD791	Approved
0.5789	Remote Similarity	NPD15	Approved
0.5783	Remote Similarity	NPD5369	Approved
0.5765	Remote Similarity	NPD3668	Phase 3
0.5765	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.575	Remote Similarity	NPD1346	Approved
0.5745	Remote Similarity	NPD7640	Approved
0.5745	Remote Similarity	NPD7639	Approved
0.5699	Remote Similarity	NPD6084	Phase 2
0.5699	Remote Similarity	NPD4755	Approved
0.5699	Remote Similarity	NPD6083	Phase 2
0.5698	Remote Similarity	NPD1694	Approved
0.5684	Remote Similarity	NPD5344	Discontinued
0.5682	Remote Similarity	NPD4723	Approved
0.5682	Remote Similarity	NPD4722	Approved
0.567	Remote Similarity	NPD5141	Approved
0.5667	Remote Similarity	NPD7637	Suspended
0.5667	Remote Similarity	NPD6411	Approved
0.5663	Remote Similarity	NPD5368	Approved
0.5652	Remote Similarity	NPD5695	Phase 3
0.5647	Remote Similarity	NPD4788	Approved
0.5638	Remote Similarity	NPD4225	Approved
0.5638	Remote Similarity	NPD7638	Approved
0.5632	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD4249	Approved
0.5625	Remote Similarity	NPD8039	Approved
0.561	Remote Similarity	NPD3617	Approved
0.5604	Remote Similarity	NPD6399	Phase 3

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