NPASS Compound

Structure

CID191233 OpenBabel06191715572D 22 22 0 0 1 0 0 0 0 0999 V2000 2.0803 -3.8149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7343 -0.1985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6810 3.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4445 2.1990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4328 -2.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0817 -3.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2803 -1.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5919 1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6277 -2.8716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 -2.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2630 -0.3032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7184 -1.1419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9680 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9190 -1.0084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -1.3685 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 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 21 1 0 0 0 0 6 10 1 0 0 0 0 8 16 1 0 0 0 0 10 11 2 0 0 0 0 11 15 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 7 1 6 0 0 0 16 17 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 9 1 6 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.22
Volume:	344.449
LogP:	4.692
LogD:	4.549
LogS:	-5.185
# Rotatable Bonds:	9
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	4.495
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.529
MDCK Permeability:	2.710028456931468e-05
Pgp-inhibitor:	0.915
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.228
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	98.6957015991211%
Volume Distribution (VD):	1.206
Pgp-substrate:	2.4898502826690674%

ADMET: Metabolism

CYP1A2-inhibitor:	0.883
CYP1A2-substrate:	0.71
CYP2C19-inhibitor:	0.905
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.863
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.925
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.964
CYP3A4-substrate:	0.509

ADMET: Excretion

Clearance (CL):	3.935
Half-life (T1/2):	0.321

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.877
Drug-inuced Liver Injury (DILI):	0.268
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.336
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.687
Carcinogencity:	0.068
Eye Corrosion:	0.005
Eye Irritation:	0.166
Respiratory Toxicity:	0.887

Download Data

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

Natural Product: NPC191233

Natural Product ID:	NPC191233
*Common Name:**	(2Z,6R,8R,9E)-Methyl 3,6-Epoxy-4,6,8-Triethyl-2,4,9-Dodecatrienoate
IUPAC Name:	methyl (2Z)-2-[(5R)-3,5-diethyl-5-[(E,2R)-2-ethylhex-3-enyl]furan-2-ylidene]acetate
Synonyms:
Standard InCHIKey:	KQEJJCDYCOPPSL-NMKLUNCLSA-N
Standard InCHI:	InChI=1S/C19H30O3/c1-6-10-11-15(7-2)13-19(9-4)14-16(8-3)17(22-19)12-18(20)21-5/h10-12,14-15H,6-9,13H2,1-5H3/b11-10+,17-12-/t15-,19+/m0/s1
SMILES:	CC/C=C/[C@@H](C[C@]1(CC)C=C(/C(=C/C(=O)OC)/O1)CC)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255878
PubChem CID:	11573100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans

*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
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO23381	Echinodorus macrophyllus	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757722]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14703354]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800643]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	Brazil	n.a.	PMID[18177008]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO33167	plakinastrella mamillaris	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934537]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO19077	Nyssa sylvatica	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23381	Echinodorus macrophyllus	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23121	Hedycarya angustifolia	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6704	Aspergillus navahoensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19077	Nyssa sylvatica	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7363	Phaedranassa dubia	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	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	15
Others	3

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	3
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	9.6	ug.mL-1	PMID[496060]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	7.2	ug.mL-1	PMID[496060]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	=	11.4	ug.mL-1	PMID[496060]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	8.6	ug.mL-1	PMID[496060]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100000.0	nM	PMID[496062]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[496062]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	800.0	nM	PMID[496062]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2600.0	nM	PMID[496062]
NPT1219	Organism	Leishmania chagasi	Leishmania chagasi	IC50	=	8.5	ug.mL-1	PMID[496060]
NPT1219	Organism	Leishmania chagasi	Leishmania chagasi	IC50	=	1.6	ug.mL-1	PMID[496060]
NPT27	Others	Unspecified		Activity	=	7.24	%	PMID[496060]
NPT27	Others	Unspecified		IC50	=	30.2	ug.mL-1	PMID[496060]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[496060]
NPT2	Others	Unspecified		Selectivity index	=	18.6	n.a.	PMID[496060]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	16.5	ug.mL-1	PMID[496060]
NPT2	Others	Unspecified		Selectivity index	=	1.8	n.a.	PMID[496060]

☑ 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 NPC191233 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	173
0.1-0.2	1545
0.2-0.3	8856
0.3-0.4	19249
0.4-0.5	8382
0.5-0.6	3583
0.6-0.7	793
0.7-0.8	105
0.8-0.85	3
0.85-0.9	2
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9836	High Similarity	NPC220766
0.9531	High Similarity	NPC470693
0.9231	High Similarity	NPC232812
0.9091	High Similarity	NPC37929
0.9091	High Similarity	NPC64234
0.8971	High Similarity	NPC470686
0.8615	High Similarity	NPC470688
0.8116	Intermediate Similarity	NPC265574
0.8088	Intermediate Similarity	NPC472266
0.8082	Intermediate Similarity	NPC473825
0.7971	Intermediate Similarity	NPC276290
0.7846	Intermediate Similarity	NPC133600
0.7826	Intermediate Similarity	NPC21998
0.7794	Intermediate Similarity	NPC182794
0.7778	Intermediate Similarity	NPC478117
0.7778	Intermediate Similarity	NPC287878
0.7761	Intermediate Similarity	NPC210303
0.7761	Intermediate Similarity	NPC44343
0.7761	Intermediate Similarity	NPC179087
0.7761	Intermediate Similarity	NPC217940
0.7761	Intermediate Similarity	NPC155849
0.7746	Intermediate Similarity	NPC315285
0.7746	Intermediate Similarity	NPC316029
0.7714	Intermediate Similarity	NPC313444
0.7681	Intermediate Similarity	NPC315115
0.7671	Intermediate Similarity	NPC474758
0.7639	Intermediate Similarity	NPC181587
0.7625	Intermediate Similarity	NPC291712
0.76	Intermediate Similarity	NPC68156
0.76	Intermediate Similarity	NPC471225
0.76	Intermediate Similarity	NPC54996
0.7568	Intermediate Similarity	NPC329852
0.7536	Intermediate Similarity	NPC471566
0.7536	Intermediate Similarity	NPC471556
0.75	Intermediate Similarity	NPC315597
0.7465	Intermediate Similarity	NPC474823
0.7465	Intermediate Similarity	NPC470256
0.7463	Intermediate Similarity	NPC19241
0.7436	Intermediate Similarity	NPC42470
0.7432	Intermediate Similarity	NPC294434
0.7432	Intermediate Similarity	NPC15499
0.7432	Intermediate Similarity	NPC259599
0.7432	Intermediate Similarity	NPC117746
0.7429	Intermediate Similarity	NPC116013
0.7419	Intermediate Similarity	NPC148056
0.7403	Intermediate Similarity	NPC271632
0.7397	Intermediate Similarity	NPC316185
0.7391	Intermediate Similarity	NPC34883
0.7385	Intermediate Similarity	NPC86948
0.7385	Intermediate Similarity	NPC96663
0.7377	Intermediate Similarity	NPC15912
0.7368	Intermediate Similarity	NPC315394
0.7361	Intermediate Similarity	NPC151481
0.7361	Intermediate Similarity	NPC475004
0.7344	Intermediate Similarity	NPC478120
0.7342	Intermediate Similarity	NPC474439
0.7342	Intermediate Similarity	NPC474028
0.7324	Intermediate Similarity	NPC194871
0.7324	Intermediate Similarity	NPC225272
0.7313	Intermediate Similarity	NPC286189
0.7308	Intermediate Similarity	NPC268827
0.7302	Intermediate Similarity	NPC151919
0.7297	Intermediate Similarity	NPC222244
0.7297	Intermediate Similarity	NPC16349
0.7286	Intermediate Similarity	NPC133904
0.7286	Intermediate Similarity	NPC471565
0.7284	Intermediate Similarity	NPC281172
0.7273	Intermediate Similarity	NPC474005
0.7273	Intermediate Similarity	NPC99182
0.726	Intermediate Similarity	NPC59558
0.726	Intermediate Similarity	NPC67183
0.7258	Intermediate Similarity	NPC27264
0.725	Intermediate Similarity	NPC475714
0.7237	Intermediate Similarity	NPC123360
0.7237	Intermediate Similarity	NPC4509
0.7229	Intermediate Similarity	NPC260343
0.7222	Intermediate Similarity	NPC218477
0.7215	Intermediate Similarity	NPC325031
0.7206	Intermediate Similarity	NPC429928
0.72	Intermediate Similarity	NPC107654
0.72	Intermediate Similarity	NPC315843
0.72	Intermediate Similarity	NPC476355
0.7183	Intermediate Similarity	NPC248125
0.7162	Intermediate Similarity	NPC163003
0.7162	Intermediate Similarity	NPC257618
0.716	Intermediate Similarity	NPC475706
0.7143	Intermediate Similarity	NPC180290
0.7143	Intermediate Similarity	NPC242877
0.7143	Intermediate Similarity	NPC226066
0.7143	Intermediate Similarity	NPC316324
0.7143	Intermediate Similarity	NPC57744
0.7143	Intermediate Similarity	NPC64913
0.7125	Intermediate Similarity	NPC16321
0.7123	Intermediate Similarity	NPC269841
0.7121	Intermediate Similarity	NPC221763
0.7121	Intermediate Similarity	NPC245002
0.7105	Intermediate Similarity	NPC329826
0.7105	Intermediate Similarity	NPC469414
0.7105	Intermediate Similarity	NPC68624
0.7101	Intermediate Similarity	NPC151648
0.7093	Intermediate Similarity	NPC282644
0.7093	Intermediate Similarity	NPC29798
0.7073	Intermediate Similarity	NPC474424
0.7073	Intermediate Similarity	NPC130030
0.7067	Intermediate Similarity	NPC238948
0.7067	Intermediate Similarity	NPC476490
0.7067	Intermediate Similarity	NPC276336
0.7067	Intermediate Similarity	NPC476489
0.7067	Intermediate Similarity	NPC215745
0.7067	Intermediate Similarity	NPC12815
0.7059	Intermediate Similarity	NPC143810
0.7059	Intermediate Similarity	NPC83838
0.7051	Intermediate Similarity	NPC267231
0.7051	Intermediate Similarity	NPC184737
0.7051	Intermediate Similarity	NPC471220
0.7051	Intermediate Similarity	NPC128276
0.7051	Intermediate Similarity	NPC253749
0.7049	Intermediate Similarity	NPC128280
0.7031	Intermediate Similarity	NPC106531
0.7027	Intermediate Similarity	NPC329904
0.7027	Intermediate Similarity	NPC473361
0.7027	Intermediate Similarity	NPC469660
0.7024	Intermediate Similarity	NPC471956
0.7024	Intermediate Similarity	NPC472302
0.7015	Intermediate Similarity	NPC474825
0.7013	Intermediate Similarity	NPC301525
0.7013	Intermediate Similarity	NPC27205
0.7011	Intermediate Similarity	NPC143210
0.7	Intermediate Similarity	NPC473737
0.7	Intermediate Similarity	NPC322457
0.7	Intermediate Similarity	NPC474658
0.7	Intermediate Similarity	NPC132243
0.6986	Remote Similarity	NPC287705
0.6986	Remote Similarity	NPC310210
0.6984	Remote Similarity	NPC289388
0.6977	Remote Similarity	NPC175842
0.6977	Remote Similarity	NPC193396
0.6977	Remote Similarity	NPC32494
0.6977	Remote Similarity	NPC32944
0.6977	Remote Similarity	NPC166110
0.6974	Remote Similarity	NPC140287
0.697	Remote Similarity	NPC173157
0.6962	Remote Similarity	NPC63649
0.6962	Remote Similarity	NPC264227
0.6962	Remote Similarity	NPC472965
0.6962	Remote Similarity	NPC178277
0.6962	Remote Similarity	NPC471537
0.6957	Remote Similarity	NPC130953
0.6957	Remote Similarity	NPC127824
0.6951	Remote Similarity	NPC14575
0.6951	Remote Similarity	NPC196487
0.6944	Remote Similarity	NPC37382
0.6941	Remote Similarity	NPC95364
0.6941	Remote Similarity	NPC142159
0.6933	Remote Similarity	NPC477084
0.6932	Remote Similarity	NPC12727
0.6923	Remote Similarity	NPC262747
0.6923	Remote Similarity	NPC476439
0.6914	Remote Similarity	NPC94200
0.6914	Remote Similarity	NPC221231
0.6914	Remote Similarity	NPC471326
0.6914	Remote Similarity	NPC324170
0.6914	Remote Similarity	NPC268122
0.6912	Remote Similarity	NPC189700
0.6905	Remote Similarity	NPC125925
0.6901	Remote Similarity	NPC477457
0.6901	Remote Similarity	NPC477456
0.6897	Remote Similarity	NPC248193
0.6897	Remote Similarity	NPC59646
0.6897	Remote Similarity	NPC1108
0.6892	Remote Similarity	NPC473603
0.6892	Remote Similarity	NPC476591
0.6892	Remote Similarity	NPC476059
0.6892	Remote Similarity	NPC101622
0.6892	Remote Similarity	NPC88877
0.6892	Remote Similarity	NPC473277
0.6885	Remote Similarity	NPC270706
0.6875	Remote Similarity	NPC244452
0.6875	Remote Similarity	NPC160582
0.6867	Remote Similarity	NPC471185
0.6867	Remote Similarity	NPC67081
0.6867	Remote Similarity	NPC215364
0.6867	Remote Similarity	NPC471223
0.6866	Remote Similarity	NPC141699
0.6866	Remote Similarity	NPC150717
0.686	Remote Similarity	NPC224270
0.686	Remote Similarity	NPC3436
0.6857	Remote Similarity	NPC55376
0.6857	Remote Similarity	NPC15193
0.6849	Remote Similarity	NPC203335
0.6849	Remote Similarity	NPC132286
0.6842	Remote Similarity	NPC58956
0.6842	Remote Similarity	NPC474705
0.6842	Remote Similarity	NPC269206
0.6842	Remote Similarity	NPC295633
0.6835	Remote Similarity	NPC209135
0.6835	Remote Similarity	NPC474816
0.6835	Remote Similarity	NPC299235
0.6835	Remote Similarity	NPC93763
0.6835	Remote Similarity	NPC108816

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 NPC191233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1787
0.2-0.3	4506
0.3-0.4	2113
0.4-0.5	465
0.5-0.6	100
0.6-0.7	13
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
0.7794	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.662	Remote Similarity	NPD4193	Approved
0.662	Remote Similarity	NPD4191	Approved
0.662	Remote Similarity	NPD4192	Approved
0.662	Remote Similarity	NPD4194	Approved
0.6615	Remote Similarity	NPD6927	Phase 3
0.6562	Remote Similarity	NPD4220	Pre-registration
0.6506	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7838	Discovery
0.6235	Remote Similarity	NPD7154	Phase 3
0.6136	Remote Similarity	NPD1282	Approved
0.6098	Remote Similarity	NPD4756	Discovery
0.6092	Remote Similarity	NPD1694	Approved
0.6027	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6648	Approved
0.5909	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5343	Approved
0.5882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4249	Approved
0.5824	Remote Similarity	NPD6051	Approved
0.5778	Remote Similarity	NPD4250	Approved
0.5778	Remote Similarity	NPD4251	Approved
0.5761	Remote Similarity	NPD5207	Approved
0.5761	Remote Similarity	NPD6698	Approved
0.5761	Remote Similarity	NPD5785	Approved
0.5761	Remote Similarity	NPD46	Approved
0.5743	Remote Similarity	NPD3134	Approved
0.5728	Remote Similarity	NPD2067	Discontinued
0.57	Remote Similarity	NPD5909	Discontinued
0.5699	Remote Similarity	NPD5694	Approved
0.5699	Remote Similarity	NPD5693	Phase 1
0.5699	Remote Similarity	NPD7637	Suspended
0.5698	Remote Similarity	NPD4821	Approved
0.5698	Remote Similarity	NPD4819	Approved
0.5698	Remote Similarity	NPD4822	Approved
0.5698	Remote Similarity	NPD4820	Approved
0.5692	Remote Similarity	NPD6096	Approved
0.5692	Remote Similarity	NPD6097	Approved
0.5682	Remote Similarity	NPD5362	Discontinued
0.567	Remote Similarity	NPD5926	Approved
0.5652	Remote Similarity	NPD1695	Approved
0.5647	Remote Similarity	NPD4268	Approved
0.5647	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD4271	Approved
0.5641	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD539	Approved
0.5616	Remote Similarity	NPD8779	Phase 3
0.5606	Remote Similarity	NPD3174	Discontinued

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