NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	164.12
Volume:	191.137
LogP:	3.979
LogD:	3.806
LogS:	-4.249
# Rotatable Bonds:	2
TPSA:	9.23
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	1.546
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.462
MDCK Permeability:	2.0873181711067446e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.066
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.823
Plasma Protein Binding (PPB):	95.09947967529297%
Volume Distribution (VD):	2.77
Pgp-substrate:	5.408719539642334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.804
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.513
CYP2C9-substrate:	0.8
CYP2D6-inhibitor:	0.601
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.252
CYP3A4-substrate:	0.603

ADMET: Excretion

Clearance (CL):	8.666
Half-life (T1/2):	0.343

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.526
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.133
Carcinogencity:	0.358
Eye Corrosion:	0.906
Eye Irritation:	0.989
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC12870

Natural Product ID:	NPC12870
*Common Name:**	2-Methoxy-1-Methyl-4-Propan-2-Ylbenzene
IUPAC Name:	2-methoxy-1-methyl-4-propan-2-ylbenzene
Synonyms:	O-Methylcarvacrol
Standard InCHIKey:	YVLHTQPPMZOCOW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O/c1-8(2)10-6-5-9(3)11(7-10)12-4/h5-8H,1-4H3
SMILES:	CC(C)c1ccc(C)c(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464709
PubChem CID:	80790
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic 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
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12088434]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[12398547]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[18164718]
NPO40258	Oxandra espintana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919589]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[547813]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17550	Origanum onites	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14108	Nardostachys jatamansi	Species	Caprifoliaceae	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
NPO23226	NPC12870	n.a.	Plant	6.1	0.7	11.5	mg/100g	Database [DUKE]
NPO17550	NPC12870	Other	Shoot	3.25	0	6.5	mg/100g	Database [DUKE]

☑ 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
Others	6
Potency	3

Activity Type	# Activity
Individual Protein	1
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	9277.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	16353.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	14575	nM	PubChem BioAssay data set
NPT1208	Organism	Leishmania braziliensis	Leishmania braziliensis	IC90	=	25.0	ug	PMID[528183]
NPT1219	Organism	Leishmania chagasi	Leishmania chagasi	IC90	=	25.0	ug	PMID[528183]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC90	=	25.0	ug	PMID[528183]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC90	>	100.0	ug	PMID[528183]

☑ 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 NPC12870 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	477
0.1-0.2	2078
0.2-0.3	6220
0.3-0.4	12935
0.4-0.5	4383
0.5-0.6	9847
0.6-0.7	5202
0.7-0.8	1461
0.8-0.85	75
0.85-0.9	14
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC24327
0.9495	High Similarity	NPC30416
0.9175	High Similarity	NPC470161
0.9038	High Similarity	NPC470723
0.8952	High Similarity	NPC280760
0.8796	High Similarity	NPC312105
0.8716	High Similarity	NPC25648
0.8704	High Similarity	NPC283169
0.8679	High Similarity	NPC275627
0.866	High Similarity	NPC321956
0.8654	High Similarity	NPC233320
0.86	High Similarity	NPC6597
0.86	High Similarity	NPC79241
0.8557	High Similarity	NPC71853
0.8544	High Similarity	NPC241224
0.8529	High Similarity	NPC300166
0.85	High Similarity	NPC259512
0.85	High Similarity	NPC312132
0.8454	Intermediate Similarity	NPC259134
0.8454	Intermediate Similarity	NPC177844
0.8454	Intermediate Similarity	NPC99886
0.8454	Intermediate Similarity	NPC8002
0.8431	Intermediate Similarity	NPC72729
0.8426	Intermediate Similarity	NPC228452
0.8426	Intermediate Similarity	NPC98372
0.8416	Intermediate Similarity	NPC95755
0.8407	Intermediate Similarity	NPC322569
0.8396	Intermediate Similarity	NPC75440
0.8381	Intermediate Similarity	NPC326801
0.8365	Intermediate Similarity	NPC475225
0.8365	Intermediate Similarity	NPC292792
0.8349	Intermediate Similarity	NPC165106
0.8333	Intermediate Similarity	NPC33675
0.8333	Intermediate Similarity	NPC299762
0.8304	Intermediate Similarity	NPC63010
0.8304	Intermediate Similarity	NPC190514
0.83	Intermediate Similarity	NPC471581
0.8288	Intermediate Similarity	NPC33900
0.8269	Intermediate Similarity	NPC235762
0.8269	Intermediate Similarity	NPC471228
0.8261	Intermediate Similarity	NPC152946
0.8261	Intermediate Similarity	NPC188997
0.8246	Intermediate Similarity	NPC212559
0.8246	Intermediate Similarity	NPC129176
0.8241	Intermediate Similarity	NPC2682
0.8241	Intermediate Similarity	NPC303521
0.8241	Intermediate Similarity	NPC475852
0.823	Intermediate Similarity	NPC471449
0.823	Intermediate Similarity	NPC184302
0.823	Intermediate Similarity	NPC98748
0.823	Intermediate Similarity	NPC51341
0.8224	Intermediate Similarity	NPC241549
0.8224	Intermediate Similarity	NPC201959
0.8198	Intermediate Similarity	NPC808
0.8198	Intermediate Similarity	NPC475815
0.8198	Intermediate Similarity	NPC47194
0.8198	Intermediate Similarity	NPC473264
0.819	Intermediate Similarity	NPC261992
0.8182	Intermediate Similarity	NPC141003
0.8182	Intermediate Similarity	NPC35344
0.8174	Intermediate Similarity	NPC475839
0.8173	Intermediate Similarity	NPC310905
0.8173	Intermediate Similarity	NPC252105
0.8173	Intermediate Similarity	NPC12714
0.8173	Intermediate Similarity	NPC84325
0.8165	Intermediate Similarity	NPC195873
0.8155	Intermediate Similarity	NPC100870
0.8142	Intermediate Similarity	NPC171023
0.8131	Intermediate Similarity	NPC66834
0.8125	Intermediate Similarity	NPC150624
0.8125	Intermediate Similarity	NPC9341
0.8125	Intermediate Similarity	NPC81067
0.812	Intermediate Similarity	NPC75432
0.8108	Intermediate Similarity	NPC470837
0.81	Intermediate Similarity	NPC231150
0.8091	Intermediate Similarity	NPC26615
0.8087	Intermediate Similarity	NPC277798
0.8087	Intermediate Similarity	NPC100108
0.8087	Intermediate Similarity	NPC96423
0.8077	Intermediate Similarity	NPC174911
0.8073	Intermediate Similarity	NPC168657
0.8073	Intermediate Similarity	NPC137685
0.8073	Intermediate Similarity	NPC473809
0.8053	Intermediate Similarity	NPC221549
0.8053	Intermediate Similarity	NPC33270
0.8053	Intermediate Similarity	NPC69261
0.8053	Intermediate Similarity	NPC244816
0.8053	Intermediate Similarity	NPC50521
0.8051	Intermediate Similarity	NPC76119
0.8051	Intermediate Similarity	NPC4286
0.8051	Intermediate Similarity	NPC170749
0.8037	Intermediate Similarity	NPC113457
0.8019	Intermediate Similarity	NPC108875
0.8019	Intermediate Similarity	NPC12987
0.8019	Intermediate Similarity	NPC474603
0.8019	Intermediate Similarity	NPC38079
0.8018	Intermediate Similarity	NPC190212
0.8017	Intermediate Similarity	NPC168707
0.8017	Intermediate Similarity	NPC48623
0.8017	Intermediate Similarity	NPC14287
0.8	Intermediate Similarity	NPC103916
0.7982	Intermediate Similarity	NPC329980
0.7982	Intermediate Similarity	NPC474040
0.7982	Intermediate Similarity	NPC283616
0.7981	Intermediate Similarity	NPC471576
0.7963	Intermediate Similarity	NPC186469
0.7963	Intermediate Similarity	NPC258171
0.7963	Intermediate Similarity	NPC35543
0.7949	Intermediate Similarity	NPC476332
0.7949	Intermediate Similarity	NPC18128
0.7949	Intermediate Similarity	NPC473464
0.7949	Intermediate Similarity	NPC77789
0.7946	Intermediate Similarity	NPC22610
0.7946	Intermediate Similarity	NPC276737
0.7944	Intermediate Similarity	NPC473855
0.7944	Intermediate Similarity	NPC227255
0.7944	Intermediate Similarity	NPC117115
0.7944	Intermediate Similarity	NPC288760
0.7944	Intermediate Similarity	NPC47284
0.7944	Intermediate Similarity	NPC470393
0.7944	Intermediate Similarity	NPC475269
0.7941	Intermediate Similarity	NPC152415
0.7941	Intermediate Similarity	NPC245187
0.7931	Intermediate Similarity	NPC218753
0.7931	Intermediate Similarity	NPC45663
0.7928	Intermediate Similarity	NPC474920
0.7928	Intermediate Similarity	NPC199462
0.7925	Intermediate Similarity	NPC298224
0.7913	Intermediate Similarity	NPC310338
0.7913	Intermediate Similarity	NPC281298
0.7899	Intermediate Similarity	NPC105031
0.7899	Intermediate Similarity	NPC470726
0.7895	Intermediate Similarity	NPC238176
0.7895	Intermediate Similarity	NPC187993
0.789	Intermediate Similarity	NPC64586
0.789	Intermediate Similarity	NPC245115
0.7885	Intermediate Similarity	NPC175298
0.7885	Intermediate Similarity	NPC77492
0.7881	Intermediate Similarity	NPC96940
0.7876	Intermediate Similarity	NPC232165
0.7876	Intermediate Similarity	NPC167934
0.7876	Intermediate Similarity	NPC473718
0.7876	Intermediate Similarity	NPC53906
0.787	Intermediate Similarity	NPC21594
0.787	Intermediate Similarity	NPC310456
0.787	Intermediate Similarity	NPC53740
0.7857	Intermediate Similarity	NPC109241
0.7857	Intermediate Similarity	NPC204120
0.785	Intermediate Similarity	NPC130817
0.785	Intermediate Similarity	NPC38209
0.7845	Intermediate Similarity	NPC474131
0.7845	Intermediate Similarity	NPC242885
0.7845	Intermediate Similarity	NPC56214
0.7845	Intermediate Similarity	NPC117780
0.7845	Intermediate Similarity	NPC344161
0.7845	Intermediate Similarity	NPC95614
0.7845	Intermediate Similarity	NPC227217
0.7845	Intermediate Similarity	NPC165133
0.7845	Intermediate Similarity	NPC232316
0.7845	Intermediate Similarity	NPC328485
0.7843	Intermediate Similarity	NPC3358
0.7843	Intermediate Similarity	NPC306884
0.7843	Intermediate Similarity	NPC162314
0.7843	Intermediate Similarity	NPC94139
0.7843	Intermediate Similarity	NPC210497
0.7843	Intermediate Similarity	NPC147284
0.7843	Intermediate Similarity	NPC55903
0.7838	Intermediate Similarity	NPC173746
0.7838	Intermediate Similarity	NPC156840
0.7838	Intermediate Similarity	NPC8547
0.7838	Intermediate Similarity	NPC54373
0.7838	Intermediate Similarity	NPC21890
0.7838	Intermediate Similarity	NPC257124
0.7833	Intermediate Similarity	NPC470724
0.7833	Intermediate Similarity	NPC245060
0.7833	Intermediate Similarity	NPC474737
0.7833	Intermediate Similarity	NPC329272
0.783	Intermediate Similarity	NPC51633
0.783	Intermediate Similarity	NPC477685
0.7826	Intermediate Similarity	NPC474612
0.7822	Intermediate Similarity	NPC192
0.7818	Intermediate Similarity	NPC58865
0.7818	Intermediate Similarity	NPC474272
0.7818	Intermediate Similarity	NPC82016
0.7815	Intermediate Similarity	NPC248557
0.7815	Intermediate Similarity	NPC61685
0.7815	Intermediate Similarity	NPC56332
0.7807	Intermediate Similarity	NPC69539
0.7807	Intermediate Similarity	NPC141090
0.78	Intermediate Similarity	NPC27974
0.7798	Intermediate Similarity	NPC194034
0.7798	Intermediate Similarity	NPC151477
0.7798	Intermediate Similarity	NPC227894
0.7797	Intermediate Similarity	NPC30462
0.7789	Intermediate Similarity	NPC124576
0.7788	Intermediate Similarity	NPC87563
0.7788	Intermediate Similarity	NPC41851
0.7778	Intermediate Similarity	NPC102639
0.7769	Intermediate Similarity	NPC473221
0.7769	Intermediate Similarity	NPC186889

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 NPC12870 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	468
0.1-0.2	1022
0.2-0.3	1463
0.3-0.4	2753
0.4-0.5	1764
0.5-0.6	1086
0.6-0.7	470
0.7-0.8	116
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.85	High Similarity	NPD288	Approved
0.84	Intermediate Similarity	NPD844	Approved
0.8393	Intermediate Similarity	NPD5691	Approved
0.8349	Intermediate Similarity	NPD5283	Phase 1
0.8319	Intermediate Similarity	NPD4626	Approved
0.8165	Intermediate Similarity	NPD1139	Approved
0.8165	Intermediate Similarity	NPD1137	Approved
0.8091	Intermediate Similarity	NPD1138	Approved
0.807	Intermediate Similarity	NPD1651	Approved
0.8036	Intermediate Similarity	NPD6671	Approved
0.789	Intermediate Similarity	NPD2684	Approved
0.7881	Intermediate Similarity	NPD4749	Approved
0.7881	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD709	Approved
0.7863	Intermediate Similarity	NPD1611	Approved
0.7863	Intermediate Similarity	NPD1281	Approved
0.7845	Intermediate Similarity	NPD1778	Approved
0.7843	Intermediate Similarity	NPD845	Approved
0.7838	Intermediate Similarity	NPD228	Approved
0.7833	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5451	Approved
0.7798	Intermediate Similarity	NPD290	Approved
0.7797	Intermediate Similarity	NPD2233	Approved
0.7797	Intermediate Similarity	NPD2232	Approved
0.7797	Intermediate Similarity	NPD2230	Approved
0.7769	Intermediate Similarity	NPD2237	Approved
0.7759	Intermediate Similarity	NPD3443	Approved
0.7759	Intermediate Similarity	NPD3444	Approved
0.7759	Intermediate Similarity	NPD3445	Approved
0.7736	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD5327	Phase 3
0.7719	Intermediate Similarity	NPD6387	Discontinued
0.7719	Intermediate Similarity	NPD7157	Approved
0.7719	Intermediate Similarity	NPD2557	Approved
0.7706	Intermediate Similarity	NPD3134	Approved
0.7667	Intermediate Similarity	NPD1283	Approved
0.7658	Intermediate Similarity	NPD4750	Phase 3
0.7632	Intermediate Similarity	NPD593	Approved
0.7632	Intermediate Similarity	NPD595	Approved
0.7627	Intermediate Similarity	NPD3496	Discontinued
0.7623	Intermediate Similarity	NPD1712	Approved
0.7611	Intermediate Similarity	NPD7843	Approved
0.7607	Intermediate Similarity	NPD5585	Approved
0.7596	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1398	Phase 1
0.7544	Intermediate Similarity	NPD592	Approved
0.7544	Intermediate Similarity	NPD594	Approved
0.7542	Intermediate Similarity	NPD2667	Approved
0.7542	Intermediate Similarity	NPD2668	Approved
0.7542	Intermediate Similarity	NPD17	Approved
0.7541	Intermediate Similarity	NPD4624	Approved
0.7521	Intermediate Similarity	NPD6696	Suspended
0.75	Intermediate Similarity	NPD7340	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.748	Intermediate Similarity	NPD2861	Phase 2
0.748	Intermediate Similarity	NPD4097	Suspended
0.7477	Intermediate Similarity	NPD1358	Approved
0.7477	Intermediate Similarity	NPD3020	Approved
0.7458	Intermediate Similarity	NPD3049	Approved
0.7456	Intermediate Similarity	NPD821	Approved
0.7456	Intermediate Similarity	NPD5535	Approved
0.7456	Intermediate Similarity	NPD7635	Approved
0.7455	Intermediate Similarity	NPD9697	Approved
0.744	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1669	Approved
0.7436	Intermediate Similarity	NPD7644	Approved
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7387	Intermediate Similarity	NPD968	Approved
0.7387	Intermediate Similarity	NPD1445	Approved
0.7387	Intermediate Similarity	NPD1444	Approved
0.7358	Intermediate Similarity	NPD1809	Phase 2
0.7355	Intermediate Similarity	NPD3972	Approved
0.7355	Intermediate Similarity	NPD1608	Approved
0.735	Intermediate Similarity	NPD3596	Phase 2
0.7323	Intermediate Similarity	NPD2979	Phase 3
0.7323	Intermediate Similarity	NPD4060	Phase 1
0.7321	Intermediate Similarity	NPD2342	Discontinued
0.7295	Intermediate Similarity	NPD4359	Approved
0.7288	Intermediate Similarity	NPD5536	Phase 2
0.728	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD3705	Approved
0.7258	Intermediate Similarity	NPD2798	Approved
0.7258	Intermediate Similarity	NPD7905	Discontinued
0.725	Intermediate Similarity	NPD2554	Approved
0.725	Intermediate Similarity	NPD2556	Approved
0.7241	Intermediate Similarity	NPD495	Approved
0.7241	Intermediate Similarity	NPD496	Approved
0.7241	Intermediate Similarity	NPD498	Approved
0.7241	Intermediate Similarity	NPD1241	Discontinued
0.7236	Intermediate Similarity	NPD2922	Phase 1
0.7227	Intermediate Similarity	NPD2486	Discontinued
0.7227	Intermediate Similarity	NPD6580	Approved
0.7227	Intermediate Similarity	NPD6581	Approved
0.7222	Intermediate Similarity	NPD1024	Discontinued
0.7213	Intermediate Similarity	NPD2235	Phase 2
0.7213	Intermediate Similarity	NPD2231	Phase 2
0.7209	Intermediate Similarity	NPD2157	Approved
0.7197	Intermediate Similarity	NPD1391	Approved
0.7196	Intermediate Similarity	NPD2859	Approved
0.7196	Intermediate Similarity	NPD2860	Approved
0.7193	Intermediate Similarity	NPD3022	Approved
0.7193	Intermediate Similarity	NPD1792	Phase 2
0.7193	Intermediate Similarity	NPD3021	Approved
0.7188	Intermediate Similarity	NPD3109	Approved
0.7188	Intermediate Similarity	NPD4140	Approved
0.7188	Intermediate Similarity	NPD2238	Phase 2
0.7188	Intermediate Similarity	NPD3110	Approved
0.7182	Intermediate Similarity	NPD846	Approved
0.7182	Intermediate Similarity	NPD940	Approved
0.7179	Intermediate Similarity	NPD497	Approved
0.7177	Intermediate Similarity	NPD2797	Approved
0.7167	Intermediate Similarity	NPD1357	Approved
0.7167	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1039	Discontinued
0.7165	Intermediate Similarity	NPD5109	Approved
0.7165	Intermediate Similarity	NPD5111	Phase 2
0.7165	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5110	Phase 2
0.7143	Intermediate Similarity	NPD600	Approved
0.7143	Intermediate Similarity	NPD596	Approved
0.7132	Intermediate Similarity	NPD5735	Approved
0.7121	Intermediate Similarity	NPD5763	Approved
0.7121	Intermediate Similarity	NPD5762	Approved
0.712	Intermediate Similarity	NPD3690	Phase 2
0.712	Intermediate Similarity	NPD6584	Phase 3
0.712	Intermediate Similarity	NPD3691	Phase 2
0.7115	Intermediate Similarity	NPD9295	Approved
0.7109	Intermediate Similarity	NPD8032	Phase 2
0.7109	Intermediate Similarity	NPD4474	Approved
0.7109	Intermediate Similarity	NPD4475	Approved
0.7107	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2933	Approved
0.7103	Intermediate Similarity	NPD2934	Approved
0.7099	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8651	Approved
0.7097	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD1182	Approved
0.7077	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6353	Approved
0.7073	Intermediate Similarity	NPD1840	Phase 2
0.7063	Intermediate Similarity	NPD3018	Phase 2
0.7059	Intermediate Similarity	NPD111	Approved
0.7054	Intermediate Similarity	NPD3620	Phase 2
0.7054	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3294	Phase 2
0.7049	Intermediate Similarity	NPD3847	Discontinued
0.7045	Intermediate Similarity	NPD6099	Approved
0.7045	Intermediate Similarity	NPD2531	Phase 2
0.7045	Intermediate Similarity	NPD2438	Suspended
0.7045	Intermediate Similarity	NPD6100	Approved
0.704	Intermediate Similarity	NPD4098	Discontinued
0.704	Intermediate Similarity	NPD3267	Approved
0.704	Intermediate Similarity	NPD3266	Approved
0.7031	Intermediate Similarity	NPD1336	Approved
0.7016	Intermediate Similarity	NPD1420	Approved
0.7016	Intermediate Similarity	NPD1421	Approved
0.7016	Intermediate Similarity	NPD3685	Discontinued
0.7016	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3657	Discovery
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6992	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD9365	Approved
0.6977	Remote Similarity	NPD7265	Discontinued
0.6977	Remote Similarity	NPD840	Approved
0.6977	Remote Similarity	NPD4870	Approved
0.6977	Remote Similarity	NPD839	Approved
0.6977	Remote Similarity	NPD3163	Approved
0.6977	Remote Similarity	NPD3162	Approved
0.6967	Remote Similarity	NPD5846	Approved
0.6967	Remote Similarity	NPD6516	Phase 2
0.6967	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7095	Approved
0.6953	Remote Similarity	NPD3027	Phase 3
0.6942	Remote Similarity	NPD3091	Approved
0.6935	Remote Similarity	NPD2981	Phase 2
0.6935	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD987	Approved
0.6905	Remote Similarity	NPD1794	Approved
0.6899	Remote Similarity	NPD3268	Approved
0.6894	Remote Similarity	NPD6895	Approved
0.6894	Remote Similarity	NPD6896	Approved
0.688	Remote Similarity	NPD2982	Phase 2
0.688	Remote Similarity	NPD6543	Approved
0.688	Remote Similarity	NPD6540	Phase 3
0.688	Remote Similarity	NPD6539	Approved
0.688	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6582	Phase 2
0.688	Remote Similarity	NPD6583	Phase 3
0.688	Remote Similarity	NPD2983	Phase 2
0.688	Remote Similarity	NPD6542	Approved
0.6875	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.687	Remote Similarity	NPD4618	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