NPASS Compound

Structure

NPC205615 OpenBabel07101718282D 24 23 0 0 1 0 0 0 0 0999 V2000 12.1244 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 17 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 18 2 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 1 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.26
Volume:	381.728
LogP:	5.83
LogD:	3.733
LogS:	-5.0
# Rotatable Bonds:	17
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	2.741
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.8
MDCK Permeability:	1.8930353689938784e-05
Pgp-inhibitor:	0.947
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.886
Plasma Protein Binding (PPB):	94.61541748046875%
Volume Distribution (VD):	0.676
Pgp-substrate:	2.750889539718628%

ADMET: Metabolism

CYP1A2-inhibitor:	0.381
CYP1A2-substrate:	0.655
CYP2C19-inhibitor:	0.586
CYP2C19-substrate:	0.44
CYP2C9-inhibitor:	0.468
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.582
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	3.624
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.114
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.332
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.931
Carcinogencity:	0.108
Eye Corrosion:	0.915
Eye Irritation:	0.819
Respiratory Toxicity:	0.781

Download Data

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

Natural Product: NPC205615

Natural Product ID:	NPC205615
*Common Name:**	Secokotomolide A
IUPAC Name:	methyl (E)-2-[(1R)-1-hydroxy-2-oxopropyl]hexadec-2-enoate
Synonyms:
Standard InCHIKey:	GRBBECUHXQCEBW-YMIFCHIISA-N
Standard InCHI:	InChI=1S/C20H36O4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-18(20(23)24-3)19(22)17(2)21/h16,19,22H,4-15H2,1-3H3/b18-16+/t19-/m0/s1
SMILES:	CCCCCCCCCCCCC/C=C([C@H](C(=O)C)O)/C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498253
PubChem CID:	11717097
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	stem wood	n.a.	n.a.	PMID[16180806]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[16792412]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18489163]
NPO23473	Cinnamomum kotoense	Species	Lauraceae	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
Others	65

Activity Type	# Activity
Cell Line	65

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	65.2	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	33.8	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	53.9	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	61.2	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	38.2	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	14.4	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	47.7	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	74.8	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	25.7	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	13.6	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	60.6	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	11.3	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	11.6	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	8.4	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	80.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	28.8	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	2.3	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	3.2	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	49.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	75.1	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	42.4	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	23.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	2.2	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	1.4	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	98.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	92.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	0.5	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	55.2	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	18.1	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	28.7	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	50.8	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	20.3	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	29.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	31.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	75.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	12.3	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	51.3	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	48.5	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	0.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	40.9	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	72.3	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	5.43	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	39.0	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	54.5	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	55.3	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	57.3	%	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	2.1	n.a.	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	3.5	n.a.	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	5.9	n.a.	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	9.9	n.a.	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	4.6	n.a.	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	1.7	n.a.	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	2.9	n.a.	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	3.4	n.a.	PMID[543831]
NPT165	Cell Line	HeLa	Homo sapiens	FC	=	3.9	n.a.	PMID[543831]

☑ 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 NPC205615 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	184
0.1-0.2	1914
0.2-0.3	7695
0.3-0.4	16880
0.4-0.5	9455
0.5-0.6	4648
0.6-0.7	1646
0.7-0.8	270
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC256640
1.0	High Similarity	NPC16279
0.8289	Intermediate Similarity	NPC260396
0.8205	Intermediate Similarity	NPC182292
0.8148	Intermediate Similarity	NPC229799
0.8148	Intermediate Similarity	NPC284472
0.8148	Intermediate Similarity	NPC286770
0.8077	Intermediate Similarity	NPC49302
0.8077	Intermediate Similarity	NPC474818
0.8077	Intermediate Similarity	NPC51809
0.8077	Intermediate Similarity	NPC125365
0.8077	Intermediate Similarity	NPC176329
0.8025	Intermediate Similarity	NPC475046
0.8025	Intermediate Similarity	NPC310450
0.8025	Intermediate Similarity	NPC11383
0.8025	Intermediate Similarity	NPC474959
0.7975	Intermediate Similarity	NPC279214
0.7975	Intermediate Similarity	NPC473471
0.7975	Intermediate Similarity	NPC221095
0.7949	Intermediate Similarity	NPC301207
0.7931	Intermediate Similarity	NPC469692
0.7931	Intermediate Similarity	NPC469645
0.7901	Intermediate Similarity	NPC150502
0.7857	Intermediate Similarity	NPC261721
0.7841	Intermediate Similarity	NPC121825
0.7792	Intermediate Similarity	NPC284006
0.7792	Intermediate Similarity	NPC144419
0.7738	Intermediate Similarity	NPC77971
0.7722	Intermediate Similarity	NPC209113
0.7722	Intermediate Similarity	NPC127118
0.7711	Intermediate Similarity	NPC16488
0.7692	Intermediate Similarity	NPC114727
0.7692	Intermediate Similarity	NPC476590
0.7683	Intermediate Similarity	NPC474980
0.7662	Intermediate Similarity	NPC293114
0.7647	Intermediate Similarity	NPC315395
0.7647	Intermediate Similarity	NPC316426
0.764	Intermediate Similarity	NPC469632
0.7632	Intermediate Similarity	NPC475982
0.7632	Intermediate Similarity	NPC236208
0.76	Intermediate Similarity	NPC122627
0.7568	Intermediate Similarity	NPC282760
0.7534	Intermediate Similarity	NPC68110
0.7529	Intermediate Similarity	NPC261380
0.7529	Intermediate Similarity	NPC470755
0.75	Intermediate Similarity	NPC68819
0.75	Intermediate Similarity	NPC161045
0.75	Intermediate Similarity	NPC145666
0.7471	Intermediate Similarity	NPC287089
0.747	Intermediate Similarity	NPC112868
0.7468	Intermediate Similarity	NPC227396
0.7467	Intermediate Similarity	NPC146811
0.7442	Intermediate Similarity	NPC469483
0.7436	Intermediate Similarity	NPC316185
0.7412	Intermediate Similarity	NPC474251
0.7412	Intermediate Similarity	NPC158756
0.7412	Intermediate Similarity	NPC31086
0.7412	Intermediate Similarity	NPC474865
0.7407	Intermediate Similarity	NPC473536
0.7403	Intermediate Similarity	NPC470436
0.7403	Intermediate Similarity	NPC143396
0.7397	Intermediate Similarity	NPC26810
0.7386	Intermediate Similarity	NPC14901
0.7386	Intermediate Similarity	NPC130359
0.7381	Intermediate Similarity	NPC26624
0.7381	Intermediate Similarity	NPC85772
0.7375	Intermediate Similarity	NPC161038
0.7375	Intermediate Similarity	NPC329826
0.7375	Intermediate Similarity	NPC469414
0.7368	Intermediate Similarity	NPC203335
0.7356	Intermediate Similarity	NPC471738
0.7356	Intermediate Similarity	NPC472007
0.7349	Intermediate Similarity	NPC47653
0.7342	Intermediate Similarity	NPC329890
0.734	Intermediate Similarity	NPC133907
0.734	Intermediate Similarity	NPC185141
0.734	Intermediate Similarity	NPC46998
0.734	Intermediate Similarity	NPC128733
0.734	Intermediate Similarity	NPC110443
0.7333	Intermediate Similarity	NPC475302
0.7326	Intermediate Similarity	NPC11804
0.7324	Intermediate Similarity	NPC135863
0.7324	Intermediate Similarity	NPC249850
0.7324	Intermediate Similarity	NPC293437
0.7317	Intermediate Similarity	NPC108816
0.7317	Intermediate Similarity	NPC93763
0.7317	Intermediate Similarity	NPC279532
0.7317	Intermediate Similarity	NPC318481
0.7317	Intermediate Similarity	NPC127526
0.7308	Intermediate Similarity	NPC476037
0.7308	Intermediate Similarity	NPC202011
0.7303	Intermediate Similarity	NPC473455
0.7303	Intermediate Similarity	NPC475879
0.7297	Intermediate Similarity	NPC474774
0.7294	Intermediate Similarity	NPC144415
0.7294	Intermediate Similarity	NPC477786
0.7294	Intermediate Similarity	NPC116543
0.7294	Intermediate Similarity	NPC477785
0.7294	Intermediate Similarity	NPC40746
0.7294	Intermediate Similarity	NPC169575
0.7294	Intermediate Similarity	NPC477784
0.7284	Intermediate Similarity	NPC203277
0.7273	Intermediate Similarity	NPC470256
0.7273	Intermediate Similarity	NPC476805
0.7273	Intermediate Similarity	NPC475819
0.7262	Intermediate Similarity	NPC471325
0.726	Intermediate Similarity	NPC79756
0.7253	Intermediate Similarity	NPC65829
0.725	Intermediate Similarity	NPC294434
0.725	Intermediate Similarity	NPC315843
0.725	Intermediate Similarity	NPC117746
0.725	Intermediate Similarity	NPC15499
0.725	Intermediate Similarity	NPC259599
0.7241	Intermediate Similarity	NPC210218
0.7241	Intermediate Similarity	NPC308412
0.7241	Intermediate Similarity	NPC204686
0.7241	Intermediate Similarity	NPC473687
0.7241	Intermediate Similarity	NPC477015
0.7241	Intermediate Similarity	NPC469910
0.7241	Intermediate Similarity	NPC472009
0.7241	Intermediate Similarity	NPC305475
0.7241	Intermediate Similarity	NPC134807
0.7241	Intermediate Similarity	NPC134885
0.7241	Intermediate Similarity	NPC219498
0.7241	Intermediate Similarity	NPC475461
0.7241	Intermediate Similarity	NPC279859
0.7241	Intermediate Similarity	NPC38576
0.7237	Intermediate Similarity	NPC248125
0.7229	Intermediate Similarity	NPC99651
0.7222	Intermediate Similarity	NPC223679
0.7222	Intermediate Similarity	NPC254095
0.7222	Intermediate Similarity	NPC32552
0.7215	Intermediate Similarity	NPC319163
0.7215	Intermediate Similarity	NPC84038
0.7215	Intermediate Similarity	NPC67076
0.7209	Intermediate Similarity	NPC163093
0.7209	Intermediate Similarity	NPC141193
0.7209	Intermediate Similarity	NPC96259
0.7209	Intermediate Similarity	NPC219966
0.7195	Intermediate Similarity	NPC320630
0.7195	Intermediate Similarity	NPC7563
0.7195	Intermediate Similarity	NPC116177
0.7195	Intermediate Similarity	NPC275530
0.7191	Intermediate Similarity	NPC87306
0.7191	Intermediate Similarity	NPC280612
0.7179	Intermediate Similarity	NPC476591
0.7179	Intermediate Similarity	NPC88877
0.7176	Intermediate Similarity	NPC473529
0.7176	Intermediate Similarity	NPC473712
0.7176	Intermediate Similarity	NPC473780
0.7176	Intermediate Similarity	NPC145914
0.7176	Intermediate Similarity	NPC131002
0.7176	Intermediate Similarity	NPC65930
0.7176	Intermediate Similarity	NPC11332
0.7176	Intermediate Similarity	NPC73310
0.7176	Intermediate Similarity	NPC475159
0.7176	Intermediate Similarity	NPC329829
0.7176	Intermediate Similarity	NPC94875
0.7176	Intermediate Similarity	NPC471296
0.7176	Intermediate Similarity	NPC180363
0.7162	Intermediate Similarity	NPC151648
0.716	Intermediate Similarity	NPC244166
0.716	Intermediate Similarity	NPC478196
0.716	Intermediate Similarity	NPC478192
0.716	Intermediate Similarity	NPC478194
0.716	Intermediate Similarity	NPC478193
0.716	Intermediate Similarity	NPC478191
0.716	Intermediate Similarity	NPC329852
0.716	Intermediate Similarity	NPC478195
0.7159	Intermediate Similarity	NPC72513
0.7159	Intermediate Similarity	NPC178215
0.7143	Intermediate Similarity	NPC194871
0.7143	Intermediate Similarity	NPC478097
0.7126	Intermediate Similarity	NPC125290
0.7126	Intermediate Similarity	NPC286338
0.7126	Intermediate Similarity	NPC473669
0.7126	Intermediate Similarity	NPC107986
0.7126	Intermediate Similarity	NPC473651
0.7126	Intermediate Similarity	NPC66346
0.7126	Intermediate Similarity	NPC473478
0.7126	Intermediate Similarity	NPC165162
0.7126	Intermediate Similarity	NPC1083
0.7126	Intermediate Similarity	NPC471567
0.7126	Intermediate Similarity	NPC110710
0.7126	Intermediate Similarity	NPC182383
0.7126	Intermediate Similarity	NPC477014
0.7126	Intermediate Similarity	NPC283085
0.7126	Intermediate Similarity	NPC120398
0.7126	Intermediate Similarity	NPC103284
0.7126	Intermediate Similarity	NPC132496
0.7126	Intermediate Similarity	NPC82795
0.7126	Intermediate Similarity	NPC255307
0.7126	Intermediate Similarity	NPC231009
0.7126	Intermediate Similarity	NPC477013
0.7126	Intermediate Similarity	NPC223871
0.7125	Intermediate Similarity	NPC238948
0.7125	Intermediate Similarity	NPC215745
0.7125	Intermediate Similarity	NPC329914
0.7125	Intermediate Similarity	NPC327383
0.7125	Intermediate Similarity	NPC474705

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 NPC205615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	2592
0.2-0.3	3968
0.3-0.4	1735
0.4-0.5	521
0.5-0.6	138
0.6-0.7	36
0.7-0.8	2
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
0.7303	Intermediate Similarity	NPD5785	Approved
0.7195	Intermediate Similarity	NPD4756	Discovery
0.7126	Intermediate Similarity	NPD5363	Approved
0.7027	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4252	Approved
0.6854	Remote Similarity	NPD5786	Approved
0.6782	Remote Similarity	NPD4269	Approved
0.6782	Remote Similarity	NPD5209	Approved
0.6782	Remote Similarity	NPD4270	Approved
0.6753	Remote Similarity	NPD3197	Phase 1
0.6632	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4225	Approved
0.6559	Remote Similarity	NPD6698	Approved
0.6559	Remote Similarity	NPD46	Approved
0.6552	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6110	Phase 1
0.6517	Remote Similarity	NPD7154	Phase 3
0.6512	Remote Similarity	NPD4268	Approved
0.6512	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4271	Approved
0.65	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6927	Phase 3
0.6477	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5370	Suspended
0.6442	Remote Similarity	NPD6371	Approved
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7838	Discovery
0.6375	Remote Similarity	NPD3704	Approved
0.6374	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4821	Approved
0.6364	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD4820	Approved
0.6364	Remote Similarity	NPD4819	Approved
0.6333	Remote Similarity	NPD5362	Discontinued
0.6316	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD6109	Phase 1
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.618	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5332	Approved
0.6154	Remote Similarity	NPD5331	Approved
0.6146	Remote Similarity	NPD7637	Suspended
0.6111	Remote Similarity	NPD4790	Discontinued
0.6091	Remote Similarity	NPD7115	Discovery
0.6064	Remote Similarity	NPD4251	Approved
0.6064	Remote Similarity	NPD4250	Approved
0.6061	Remote Similarity	NPD7839	Suspended
0.6044	Remote Similarity	NPD6435	Approved
0.604	Remote Similarity	NPD7639	Approved
0.604	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD4265	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD3194	Approved
0.6	Remote Similarity	NPD3196	Approved
0.6	Remote Similarity	NPD3195	Phase 2
0.6	Remote Similarity	NPD4266	Approved
0.5974	Remote Similarity	NPD8779	Phase 3
0.5957	Remote Similarity	NPD4249	Approved
0.5941	Remote Similarity	NPD7638	Approved
0.5938	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6101	Approved
0.587	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD3172	Approved
0.5865	Remote Similarity	NPD6647	Phase 2
0.5859	Remote Similarity	NPD5282	Discontinued
0.5851	Remote Similarity	NPD1694	Approved
0.5842	Remote Similarity	NPD6084	Phase 2
0.5842	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD5343	Approved
0.5825	Remote Similarity	NPD5344	Discontinued
0.5816	Remote Similarity	NPD6411	Approved
0.5795	Remote Similarity	NPD8039	Approved
0.5795	Remote Similarity	NPD1452	Discontinued
0.5794	Remote Similarity	NPD6686	Approved
0.5783	Remote Similarity	NPD7331	Phase 2
0.578	Remote Similarity	NPD6649	Approved
0.578	Remote Similarity	NPD6650	Approved
0.578	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD3732	Approved
0.5775	Remote Similarity	NPD39	Approved
0.5775	Remote Similarity	NPD4222	Approved
0.5753	Remote Similarity	NPD3173	Approved
0.5753	Remote Similarity	NPD4220	Pre-registration
0.5741	Remote Similarity	NPD6373	Approved
0.5741	Remote Similarity	NPD6372	Approved
0.5714	Remote Similarity	NPD9411	Phase 1
0.5714	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD69	Approved
0.5696	Remote Similarity	NPD9119	Approved
0.5686	Remote Similarity	NPD7902	Approved
0.5684	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD1696	Phase 3
0.5657	Remote Similarity	NPD7515	Phase 2
0.5648	Remote Similarity	NPD6899	Approved
0.5648	Remote Similarity	NPD6881	Approved
0.5644	Remote Similarity	NPD5695	Phase 3
0.5631	Remote Similarity	NPD5696	Approved
0.5607	Remote Similarity	NPD5739	Approved
0.5607	Remote Similarity	NPD6675	Approved
0.5607	Remote Similarity	NPD6402	Approved
0.5607	Remote Similarity	NPD7128	Approved
0.56	Remote Similarity	NPD6399	Phase 3
0.56	Remote Similarity	NPD28	Approved
0.56	Remote Similarity	NPD29	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