NPASS Compound

Structure

CID130302 OpenBabel06191715492D 26 31 0 0 1 0 0 0 0 0999 V2000 3.2200 -2.1348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5696 -1.5006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0843 -2.3412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7327 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5990 -0.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7328 -2.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 -2.1699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2330 -2.1348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7328 -3.0011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8663 -0.5002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8665 -3.5013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0001 -3.0011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7326 -2.0008 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8668 -1.5005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5246 -2.9793 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8664 -0.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5990 -1.5006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8664 -1.5005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8663 -1.5006 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3603 -0.6457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1741 -3.7006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7069 -0.0148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5297 -3.0838 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 0.0001 -4.0015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 18 1 0 0 0 0 7 24 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 6 1 1 0 0 0 9 11 1 0 0 0 0 10 20 1 6 0 0 0 10 25 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 1 0 0 0 12 13 1 0 0 0 0 12 26 1 1 0 0 0 13 19 1 1 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 6 0 0 0 15 19 1 6 0 0 0 15 21 1 0 0 0 0 16 22 1 1 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 19 6 1 1 0 0 0 20 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.17
Volume:	350.606
LogP:	1.993
LogD:	1.885
LogS:	-4.71
# Rotatable Bonds:	0
TPSA:	88.52
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.38
Synthetic Accessibility Score:	7.098
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.527
MDCK Permeability:	3.9442238630726933e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.52

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.182
Plasma Protein Binding (PPB):	60.871944427490234%
Volume Distribution (VD):	1.965
Pgp-substrate:	46.97828674316406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.665
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	4.89
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.215
Human Hepatotoxicity (H-HT):	0.813
Drug-inuced Liver Injury (DILI):	0.135
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.342
Carcinogencity:	0.283
Eye Corrosion:	0.008
Eye Irritation:	0.022
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC130302

Natural Product ID:	NPC130302
*Common Name:**	ZDFHFNJMFWEISA-IDCOXZCYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZDFHFNJMFWEISA-IDCOXZCYSA-N
Standard InCHI:	InChI=1S/C20H26O6/c1-8-9-6-19(15(8)21)13(12-11(9)26-12)20-7-24-16(22)14(20)18(2,3)5-4-10(20)25-17(19)23/h9-16,21-22H,1,4-7H2,2-3H3/t9-,10+,11-,12-,13-,14-,15-,16-,19+,20+/m1/s1
SMILES:	O[C@@H]1OC[C@]23[C@H]1C(C)(C)CC[C@@H]2OC(=O)[C@]12[C@H]3[C@@H]3O[C@@H]3[C@H](C1)C(=C)[C@H]2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3093768
PubChem CID:	72947453
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19697926]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2421673]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	aerial parts	Muli County, Sichuan Province, China	2011-AUG	PMID[24219809]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20470	Elaeagnus orientalis	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16409	Quercus pedunculata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1558	Ozothamnus obcordatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16021	Boletus bovinus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20543	Psydrax livida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17240	Crematogaster brevis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19889	Cereus stellatus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17508	Danae racemosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19768	Xylosalsola arbuscula	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8991	Carcinus maenas	Species	Carcinidae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[559318]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[559318]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[559318]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[559318]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[559318]

☑ 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 NPC130302 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	281
0.1-0.2	1943
0.2-0.3	5978
0.3-0.4	11665
0.4-0.5	9529
0.5-0.6	6009
0.6-0.7	5473
0.7-0.8	1675
0.8-0.85	104
0.85-0.9	27
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9604	High Similarity	NPC285927
0.9423	High Similarity	NPC255655
0.9423	High Similarity	NPC98633
0.9238	High Similarity	NPC124053
0.9208	High Similarity	NPC39683
0.9159	High Similarity	NPC285086
0.9151	High Similarity	NPC471251
0.9143	High Similarity	NPC471250
0.8952	High Similarity	NPC96333
0.8952	High Similarity	NPC88833
0.8879	High Similarity	NPC42776
0.8796	High Similarity	NPC56025
0.8774	High Similarity	NPC61071
0.8762	High Similarity	NPC101842
0.8704	High Similarity	NPC49730
0.8704	High Similarity	NPC98069
0.8679	High Similarity	NPC164600
0.8679	High Similarity	NPC103172
0.8679	High Similarity	NPC37600
0.8624	High Similarity	NPC329953
0.8624	High Similarity	NPC470311
0.8598	High Similarity	NPC469746
0.8598	High Similarity	NPC471246
0.8585	High Similarity	NPC13149
0.8585	High Similarity	NPC202793
0.8519	High Similarity	NPC232133
0.8519	High Similarity	NPC469733
0.8519	High Similarity	NPC469729
0.8505	High Similarity	NPC12823
0.8491	Intermediate Similarity	NPC139347
0.8476	Intermediate Similarity	NPC121218
0.8476	Intermediate Similarity	NPC253886
0.8468	Intermediate Similarity	NPC132668
0.844	Intermediate Similarity	NPC469983
0.844	Intermediate Similarity	NPC469744
0.8396	Intermediate Similarity	NPC309388
0.8396	Intermediate Similarity	NPC475803
0.8381	Intermediate Similarity	NPC108371
0.8381	Intermediate Similarity	NPC267921
0.8364	Intermediate Similarity	NPC471476
0.8364	Intermediate Similarity	NPC473324
0.8364	Intermediate Similarity	NPC471093
0.8333	Intermediate Similarity	NPC471249
0.8333	Intermediate Similarity	NPC295366
0.8319	Intermediate Similarity	NPC88945
0.8319	Intermediate Similarity	NPC229752
0.8318	Intermediate Similarity	NPC469985
0.8318	Intermediate Similarity	NPC87927
0.8304	Intermediate Similarity	NPC102619
0.8302	Intermediate Similarity	NPC163963
0.8302	Intermediate Similarity	NPC52899
0.8302	Intermediate Similarity	NPC471790
0.8302	Intermediate Similarity	NPC75941
0.8302	Intermediate Similarity	NPC289148
0.8302	Intermediate Similarity	NPC295276
0.8302	Intermediate Similarity	NPC14634
0.8288	Intermediate Similarity	NPC213320
0.8288	Intermediate Similarity	NPC270586
0.8288	Intermediate Similarity	NPC122339
0.8288	Intermediate Similarity	NPC63244
0.8288	Intermediate Similarity	NPC29505
0.8286	Intermediate Similarity	NPC474793
0.8273	Intermediate Similarity	NPC102741
0.8269	Intermediate Similarity	NPC193785
0.8246	Intermediate Similarity	NPC473304
0.8246	Intermediate Similarity	NPC78836
0.8246	Intermediate Similarity	NPC470171
0.8241	Intermediate Similarity	NPC47281
0.8241	Intermediate Similarity	NPC474558
0.8241	Intermediate Similarity	NPC244247
0.8224	Intermediate Similarity	NPC286519
0.8224	Intermediate Similarity	NPC148628
0.8224	Intermediate Similarity	NPC246736
0.8224	Intermediate Similarity	NPC88203
0.8224	Intermediate Similarity	NPC304832
0.8224	Intermediate Similarity	NPC170615
0.8224	Intermediate Similarity	NPC124544
0.8224	Intermediate Similarity	NPC214946
0.8224	Intermediate Similarity	NPC76866
0.8214	Intermediate Similarity	NPC474927
0.8214	Intermediate Similarity	NPC473397
0.8214	Intermediate Similarity	NPC471244
0.8214	Intermediate Similarity	NPC473352
0.8214	Intermediate Similarity	NPC471245
0.8214	Intermediate Similarity	NPC473303
0.8214	Intermediate Similarity	NPC40608
0.8208	Intermediate Similarity	NPC41971
0.8208	Intermediate Similarity	NPC287676
0.8208	Intermediate Similarity	NPC37047
0.8208	Intermediate Similarity	NPC180733
0.819	Intermediate Similarity	NPC253586
0.8182	Intermediate Similarity	NPC473410
0.8182	Intermediate Similarity	NPC63841
0.8182	Intermediate Similarity	NPC189663
0.8182	Intermediate Similarity	NPC55973
0.8182	Intermediate Similarity	NPC469845
0.8182	Intermediate Similarity	NPC469984
0.8182	Intermediate Similarity	NPC471094
0.8182	Intermediate Similarity	NPC89860
0.8165	Intermediate Similarity	NPC50535
0.8165	Intermediate Similarity	NPC4115
0.8155	Intermediate Similarity	NPC147272
0.8151	Intermediate Similarity	NPC273962
0.8151	Intermediate Similarity	NPC174367
0.8151	Intermediate Similarity	NPC47113
0.8148	Intermediate Similarity	NPC216114
0.8148	Intermediate Similarity	NPC96217
0.8148	Intermediate Similarity	NPC266
0.8142	Intermediate Similarity	NPC94141
0.8142	Intermediate Similarity	NPC471252
0.8131	Intermediate Similarity	NPC148279
0.8131	Intermediate Similarity	NPC236585
0.8131	Intermediate Similarity	NPC46848
0.8125	Intermediate Similarity	NPC94650
0.8125	Intermediate Similarity	NPC272242
0.8115	Intermediate Similarity	NPC42206
0.8113	Intermediate Similarity	NPC471038
0.8113	Intermediate Similarity	NPC78427
0.8113	Intermediate Similarity	NPC16911
0.8108	Intermediate Similarity	NPC118721
0.8108	Intermediate Similarity	NPC252679
0.8095	Intermediate Similarity	NPC13949
0.8095	Intermediate Similarity	NPC234564
0.8091	Intermediate Similarity	NPC471474
0.8091	Intermediate Similarity	NPC471461
0.8091	Intermediate Similarity	NPC186054
0.8091	Intermediate Similarity	NPC67745
0.8077	Intermediate Similarity	NPC280804
0.8073	Intermediate Similarity	NPC84928
0.8073	Intermediate Similarity	NPC98603
0.8073	Intermediate Similarity	NPC88469
0.807	Intermediate Similarity	NPC17165
0.807	Intermediate Similarity	NPC243354
0.8056	Intermediate Similarity	NPC275990
0.8056	Intermediate Similarity	NPC164551
0.8053	Intermediate Similarity	NPC145625
0.8053	Intermediate Similarity	NPC243572
0.8053	Intermediate Similarity	NPC157929
0.8039	Intermediate Similarity	NPC194642
0.8037	Intermediate Similarity	NPC94906
0.8036	Intermediate Similarity	NPC85391
0.8036	Intermediate Similarity	NPC137104
0.8036	Intermediate Similarity	NPC474786
0.8036	Intermediate Similarity	NPC106760
0.8036	Intermediate Similarity	NPC320383
0.8019	Intermediate Similarity	NPC111187
0.8019	Intermediate Similarity	NPC190080
0.8018	Intermediate Similarity	NPC218123
0.8018	Intermediate Similarity	NPC112895
0.8018	Intermediate Similarity	NPC231278
0.8018	Intermediate Similarity	NPC211224
0.8017	Intermediate Similarity	NPC473620
0.8	Intermediate Similarity	NPC56656
0.8	Intermediate Similarity	NPC28791
0.8	Intermediate Similarity	NPC307660
0.8	Intermediate Similarity	NPC130511
0.8	Intermediate Similarity	NPC470232
0.7984	Intermediate Similarity	NPC475376
0.7982	Intermediate Similarity	NPC52634
0.7982	Intermediate Similarity	NPC140723
0.7982	Intermediate Similarity	NPC159442
0.7982	Intermediate Similarity	NPC470310
0.7965	Intermediate Similarity	NPC470281
0.7963	Intermediate Similarity	NPC242666
0.7963	Intermediate Similarity	NPC475958
0.7961	Intermediate Similarity	NPC100313
0.7946	Intermediate Similarity	NPC131903
0.7946	Intermediate Similarity	NPC143706
0.7946	Intermediate Similarity	NPC472534
0.7946	Intermediate Similarity	NPC274827
0.7944	Intermediate Similarity	NPC89099
0.7944	Intermediate Similarity	NPC162459
0.7944	Intermediate Similarity	NPC28864
0.7944	Intermediate Similarity	NPC38471
0.7944	Intermediate Similarity	NPC98837
0.7944	Intermediate Similarity	NPC20479
0.7944	Intermediate Similarity	NPC472028
0.7944	Intermediate Similarity	NPC469986
0.7944	Intermediate Similarity	NPC38296
0.7944	Intermediate Similarity	NPC26270
0.7934	Intermediate Similarity	NPC305496
0.7934	Intermediate Similarity	NPC287423
0.7934	Intermediate Similarity	NPC42399
0.7928	Intermediate Similarity	NPC251824
0.7928	Intermediate Similarity	NPC78966
0.7928	Intermediate Similarity	NPC86852
0.7928	Intermediate Similarity	NPC284732
0.7925	Intermediate Similarity	NPC29410
0.7925	Intermediate Similarity	NPC256227
0.7925	Intermediate Similarity	NPC200054
0.7925	Intermediate Similarity	NPC329910
0.792	Intermediate Similarity	NPC219058
0.792	Intermediate Similarity	NPC256618
0.7909	Intermediate Similarity	NPC96268
0.7905	Intermediate Similarity	NPC475118
0.7905	Intermediate Similarity	NPC470385
0.7905	Intermediate Similarity	NPC470386
0.7895	Intermediate Similarity	NPC126691
0.7895	Intermediate Similarity	NPC476964
0.7881	Intermediate Similarity	NPC281840

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 NPC130302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	2303
0.2-0.3	3958
0.3-0.4	1738
0.4-0.5	418
0.5-0.6	276
0.6-0.7	163
0.7-0.8	25
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
0.7838	Intermediate Similarity	NPD6008	Approved
0.7661	Intermediate Similarity	NPD7319	Approved
0.7642	Intermediate Similarity	NPD8293	Discontinued
0.7603	Intermediate Similarity	NPD6370	Approved
0.7581	Intermediate Similarity	NPD7736	Approved
0.7561	Intermediate Similarity	NPD7507	Approved
0.7521	Intermediate Similarity	NPD8133	Approved
0.748	Intermediate Similarity	NPD7492	Approved
0.7438	Intermediate Similarity	NPD6054	Approved
0.7438	Intermediate Similarity	NPD6059	Approved
0.7419	Intermediate Similarity	NPD6616	Approved
0.7377	Intermediate Similarity	NPD6015	Approved
0.7377	Intermediate Similarity	NPD6016	Approved
0.736	Intermediate Similarity	NPD7078	Approved
0.7333	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5988	Approved
0.7241	Intermediate Similarity	NPD7320	Approved
0.7241	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8034	Phase 2
0.7222	Intermediate Similarity	NPD8035	Phase 2
0.7217	Intermediate Similarity	NPD6402	Approved
0.7217	Intermediate Similarity	NPD7128	Approved
0.7217	Intermediate Similarity	NPD5739	Approved
0.7217	Intermediate Similarity	NPD6675	Approved
0.7179	Intermediate Similarity	NPD6372	Approved
0.7179	Intermediate Similarity	NPD6373	Approved
0.7155	Intermediate Similarity	NPD5701	Approved
0.7155	Intermediate Similarity	NPD5697	Approved
0.7155	Intermediate Similarity	NPD6412	Phase 2
0.7154	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.713	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8328	Phase 3
0.7094	Intermediate Similarity	NPD6881	Approved
0.7094	Intermediate Similarity	NPD6899	Approved
0.708	Intermediate Similarity	NPD7639	Approved
0.708	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD6650	Approved
0.7059	Intermediate Similarity	NPD6649	Approved
0.7049	Intermediate Similarity	NPD6009	Approved
0.7049	Intermediate Similarity	NPD7115	Discovery
0.7034	Intermediate Similarity	NPD6013	Approved
0.7034	Intermediate Similarity	NPD6012	Approved
0.7034	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6014	Approved
0.7018	Intermediate Similarity	NPD1700	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6992	Remote Similarity	NPD7327	Approved
0.6992	Remote Similarity	NPD7328	Approved
0.6991	Remote Similarity	NPD7638	Approved
0.6981	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6883	Approved
0.6975	Remote Similarity	NPD7102	Approved
0.6975	Remote Similarity	NPD7290	Approved
0.696	Remote Similarity	NPD8515	Approved
0.696	Remote Similarity	NPD8513	Phase 3
0.696	Remote Similarity	NPD8516	Approved
0.696	Remote Similarity	NPD8033	Approved
0.696	Remote Similarity	NPD8517	Approved
0.6957	Remote Similarity	NPD5211	Phase 2
0.6949	Remote Similarity	NPD6686	Approved
0.6949	Remote Similarity	NPD6011	Approved
0.6942	Remote Similarity	NPD4632	Approved
0.6935	Remote Similarity	NPD7516	Approved
0.6917	Remote Similarity	NPD8130	Phase 1
0.6917	Remote Similarity	NPD6617	Approved
0.6917	Remote Similarity	NPD6869	Approved
0.6917	Remote Similarity	NPD6847	Approved
0.6903	Remote Similarity	NPD4755	Approved
0.6899	Remote Similarity	NPD6033	Approved
0.688	Remote Similarity	NPD8377	Approved
0.688	Remote Similarity	NPD8294	Approved
0.686	Remote Similarity	NPD8297	Approved
0.6842	Remote Similarity	NPD4225	Approved
0.6838	Remote Similarity	NPD5141	Approved
0.6833	Remote Similarity	NPD4634	Approved
0.6825	Remote Similarity	NPD8335	Approved
0.6825	Remote Similarity	NPD8380	Approved
0.6825	Remote Similarity	NPD8378	Approved
0.6825	Remote Similarity	NPD8296	Approved
0.6825	Remote Similarity	NPD8379	Approved
0.6783	Remote Similarity	NPD4700	Approved
0.6783	Remote Similarity	NPD5285	Approved
0.6783	Remote Similarity	NPD5286	Approved
0.6783	Remote Similarity	NPD4696	Approved
0.6777	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6411	Approved
0.675	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6053	Discontinued
0.6719	Remote Similarity	NPD6067	Discontinued
0.6719	Remote Similarity	NPD7604	Phase 2
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6694	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6274	Approved
0.6693	Remote Similarity	NPD5983	Phase 2
0.6693	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6635	Remote Similarity	NPD6114	Approved
0.6635	Remote Similarity	NPD6115	Approved
0.6635	Remote Similarity	NPD6697	Approved
0.6635	Remote Similarity	NPD6118	Approved
0.661	Remote Similarity	NPD5175	Approved
0.661	Remote Similarity	NPD5174	Approved
0.6609	Remote Similarity	NPD6083	Phase 2
0.6609	Remote Similarity	NPD6084	Phase 2
0.6607	Remote Similarity	NPD7637	Suspended
0.6581	Remote Similarity	NPD5223	Approved
0.6577	Remote Similarity	NPD6101	Approved
0.6577	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5328	Approved
0.6562	Remote Similarity	NPD7503	Approved
0.6562	Remote Similarity	NPD6921	Approved
0.6552	Remote Similarity	NPD5696	Approved
0.6549	Remote Similarity	NPD4202	Approved
0.6538	Remote Similarity	NPD6116	Phase 1
0.6535	Remote Similarity	NPD7100	Approved
0.6535	Remote Similarity	NPD7101	Approved
0.6522	Remote Similarity	NPD4697	Phase 3
0.6509	Remote Similarity	NPD6928	Phase 2
0.6508	Remote Similarity	NPD6317	Approved
0.6505	Remote Similarity	NPD3702	Approved
0.65	Remote Similarity	NPD4767	Approved
0.65	Remote Similarity	NPD4768	Approved
0.6491	Remote Similarity	NPD6001	Approved
0.6489	Remote Similarity	NPD6336	Discontinued
0.6471	Remote Similarity	NPD4754	Approved
0.6466	Remote Similarity	NPD7902	Approved
0.646	Remote Similarity	NPD6079	Approved
0.6457	Remote Similarity	NPD6335	Approved
0.6457	Remote Similarity	NPD6314	Approved
0.6457	Remote Similarity	NPD6313	Approved
0.6455	Remote Similarity	NPD3618	Phase 1
0.6446	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6117	Approved
0.6439	Remote Similarity	NPD8074	Phase 3
0.6435	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5695	Phase 3
0.6434	Remote Similarity	NPD6908	Approved
0.6434	Remote Similarity	NPD6909	Approved
0.6423	Remote Similarity	NPD6371	Approved
0.6422	Remote Similarity	NPD4786	Approved
0.6404	Remote Similarity	NPD8171	Discontinued
0.6393	Remote Similarity	NPD5128	Approved
0.6393	Remote Similarity	NPD4730	Approved
0.6393	Remote Similarity	NPD4729	Approved
0.6389	Remote Similarity	NPD3667	Approved
0.6379	Remote Similarity	NPD5222	Approved
0.6379	Remote Similarity	NPD5221	Approved
0.6379	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5282	Discontinued
0.6348	Remote Similarity	NPD7748	Approved
0.6346	Remote Similarity	NPD3703	Phase 2
0.6339	Remote Similarity	NPD6903	Approved
0.6331	Remote Similarity	NPD6334	Approved
0.6331	Remote Similarity	NPD6333	Approved
0.633	Remote Similarity	NPD4788	Approved
0.6325	Remote Similarity	NPD5173	Approved
0.6316	Remote Similarity	NPD7515	Phase 2
0.6306	Remote Similarity	NPD6684	Approved
0.6306	Remote Similarity	NPD7334	Approved
0.6306	Remote Similarity	NPD5786	Approved
0.6306	Remote Similarity	NPD5330	Approved
0.6306	Remote Similarity	NPD6409	Approved
0.6306	Remote Similarity	NPD4249	Approved
0.6306	Remote Similarity	NPD7521	Approved
0.6306	Remote Similarity	NPD7146	Approved
0.6296	Remote Similarity	NPD5956	Approved
0.629	Remote Similarity	NPD5251	Approved
0.629	Remote Similarity	NPD5250	Approved
0.629	Remote Similarity	NPD5247	Approved
0.629	Remote Similarity	NPD5248	Approved
0.629	Remote Similarity	NPD5249	Phase 3
0.6283	Remote Similarity	NPD4753	Phase 2
0.6281	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD3666	Approved
0.6273	Remote Similarity	NPD3133	Approved
0.6273	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4250	Approved
0.624	Remote Similarity	NPD5216	Approved
0.624	Remote Similarity	NPD5217	Approved
0.624	Remote Similarity	NPD5215	Approved
0.6239	Remote Similarity	NPD7839	Suspended
0.6207	Remote Similarity	NPD7900	Approved
0.6207	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5362	Discontinued
0.6174	Remote Similarity	NPD5281	Approved
0.6174	Remote Similarity	NPD5284	Approved
0.6174	Remote Similarity	NPD7983	Approved
0.6172	Remote Similarity	NPD6868	Approved
0.6161	Remote Similarity	NPD3574	Clinical (unspecified phase)

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