NPASS Compound

Structure

CID257485 OpenBabel06191716062D 35 36 0 0 1 0 0 0 0 0999 V2000 -7.2116 1.5719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8482 2.5624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4959 -0.7896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1304 -2.1717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7044 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9887 -1.3733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6720 0.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1325 0.2010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9563 -1.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4168 -2.1605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5399 -0.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8889 0.3957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8773 -2.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2439 1.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5282 -0.6879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4492 -2.0588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0534 -1.1699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1017 -0.9676 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5279 2.4324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.8919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2730 -3.7348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6214 -1.6187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3291 -1.3291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 2 0 0 0 0 4 23 1 0 0 0 0 5 29 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 21 2 0 0 0 0 10 22 1 0 0 0 0 11 22 1 0 0 0 0 12 24 2 0 0 0 0 13 27 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 29 1 0 0 0 0 18 31 1 0 0 0 0 19 23 1 0 0 0 0 19 32 2 0 0 0 0 20 24 1 0 0 0 0 20 33 1 0 0 0 0 23 25 2 0 0 0 0 25 27 1 0 0 0 0 26 24 1 6 0 0 0 26 28 1 0 0 0 0 27 30 1 6 0 0 0 28 30 1 1 0 0 0 28 34 1 0 0 0 0 29 30 1 6 0 0 0 29 35 1 0 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	538.455
LogP:	3.49
LogD:	3.052
LogS:	-4.127
# Rotatable Bonds:	11
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.143
Synthetic Accessibility Score:	5.754
Fsp3:	0.633
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	1.362200691801263e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.403
30% Bioavailability (F30%):	0.239

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.705
Plasma Protein Binding (PPB):	97.11438751220703%
Volume Distribution (VD):	1.096
Pgp-substrate:	5.007972717285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.136
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.369
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.553
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.803
CYP3A4-substrate:	0.234

ADMET: Excretion

Clearance (CL):	6.528
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.668
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.889
Carcinogencity:	0.895
Eye Corrosion:	0.008
Eye Irritation:	0.03
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC257485

Natural Product ID:	NPC257485
*Common Name:**	28-Deacetylbelamcandal
IUPAC Name:	(2Z)-2-[(3S,4S,5S,6R,10S)-4,10-dihydroxy-3-[(2E,4E)-1-hydroxy-10-methyl-6-methylideneundeca-2,4,9-trien-2-yl]-6-(3-hydroxypropyl)-10-methylspiro[4.5]decan-7-ylidene]propanal
Synonyms:	28-Deacetylbelamcandal
Standard InCHIKey:	XVFORSWJIMCHND-HWEIDYSJSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-21(2)9-6-10-22(3)11-7-12-24(20-33)26-15-17-30(28(26)34)27(13-8-18-31)25(23(4)19-32)14-16-29(30,5)35/h7,9,11-12,19,26-28,31,33-35H,3,6,8,10,13-18,20H2,1-2,4-5H3/b11-7+,24-12-,25-23-/t26-,27+,28-,29-,30-/m0/s1
SMILES:	OCCC[C@@H]1/C(=C(C=O)/C)/CC[C@]([C@]21CC[C@H]([C@@H]2O)/C(=CC=CC(=C)CCC=C(C)C)/CO)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510803
PubChem CID:	10791126
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075762]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465599]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24433009]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25036154]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28032759]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31246464]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7528	Belamcanda chinensis	Species	Iridaceae	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
ED50	1
IC50	1
Others	3

Activity Type	# Activity
Cell Line	2
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	500.0	nM	PMID[560212]
NPT116	Cell Line	HL-60	Homo sapiens	ED100	=	3000.0	nM	PMID[560212]
NPT2	Others	Unspecified		ED50	=	300.0	nM	PMID[560212]
NPT2	Others	Unspecified		IC50	=	200.0	nM	PMID[560212]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	64.3	%	PMID[560212]

☑ 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 NPC257485 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	155
0.1-0.2	936
0.2-0.3	4170
0.3-0.4	11829
0.4-0.5	12008
0.5-0.6	7930
0.6-0.7	4819
0.7-0.8	830
0.8-0.85	13
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC280203
0.8387	Intermediate Similarity	NPC13924
0.828	Intermediate Similarity	NPC474690
0.8211	Intermediate Similarity	NPC474938
0.8211	Intermediate Similarity	NPC99726
0.8211	Intermediate Similarity	NPC474785
0.8193	Intermediate Similarity	NPC78527
0.8191	Intermediate Similarity	NPC180950
0.8085	Intermediate Similarity	NPC299100
0.8022	Intermediate Similarity	NPC475772
0.7979	Intermediate Similarity	NPC214697
0.7978	Intermediate Similarity	NPC470384
0.7931	Intermediate Similarity	NPC470429
0.7895	Intermediate Similarity	NPC119562
0.7895	Intermediate Similarity	NPC279410
0.7895	Intermediate Similarity	NPC292793
0.7889	Intermediate Similarity	NPC238485
0.7889	Intermediate Similarity	NPC231310
0.7889	Intermediate Similarity	NPC205845
0.7872	Intermediate Similarity	NPC212948
0.7849	Intermediate Similarity	NPC472983
0.7835	Intermediate Similarity	NPC141401
0.7816	Intermediate Similarity	NPC476949
0.7802	Intermediate Similarity	NPC109528
0.78	Intermediate Similarity	NPC475050
0.7789	Intermediate Similarity	NPC152778
0.7789	Intermediate Similarity	NPC472942
0.7789	Intermediate Similarity	NPC162615
0.7789	Intermediate Similarity	NPC205034
0.7789	Intermediate Similarity	NPC310013
0.7778	Intermediate Similarity	NPC115899
0.7778	Intermediate Similarity	NPC79945
0.7778	Intermediate Similarity	NPC282524
0.7753	Intermediate Similarity	NPC159148
0.7753	Intermediate Similarity	NPC320525
0.7742	Intermediate Similarity	NPC292491
0.7742	Intermediate Similarity	NPC310752
0.7732	Intermediate Similarity	NPC16967
0.7732	Intermediate Similarity	NPC301534
0.7732	Intermediate Similarity	NPC250757
0.7732	Intermediate Similarity	NPC249954
0.7723	Intermediate Similarity	NPC272632
0.7717	Intermediate Similarity	NPC6391
0.7717	Intermediate Similarity	NPC261266
0.7708	Intermediate Similarity	NPC476186
0.7708	Intermediate Similarity	NPC8993
0.7708	Intermediate Similarity	NPC191521
0.7701	Intermediate Similarity	NPC85105
0.7701	Intermediate Similarity	NPC149550
0.7701	Intermediate Similarity	NPC470428
0.7692	Intermediate Similarity	NPC302360
0.7684	Intermediate Similarity	NPC41554
0.7684	Intermediate Similarity	NPC475806
0.7684	Intermediate Similarity	NPC97404
0.7677	Intermediate Similarity	NPC266955
0.7677	Intermediate Similarity	NPC154072
0.7674	Intermediate Similarity	NPC328104
0.7674	Intermediate Similarity	NPC319090
0.767	Intermediate Similarity	NPC275060
0.7667	Intermediate Similarity	NPC49964
0.7667	Intermediate Similarity	NPC2524
0.7667	Intermediate Similarity	NPC87489
0.7667	Intermediate Similarity	NPC296701
0.7667	Intermediate Similarity	NPC202389
0.7667	Intermediate Similarity	NPC101462
0.7667	Intermediate Similarity	NPC218616
0.766	Intermediate Similarity	NPC472240
0.766	Intermediate Similarity	NPC262858
0.766	Intermediate Similarity	NPC146554
0.766	Intermediate Similarity	NPC314727
0.7653	Intermediate Similarity	NPC126815
0.7647	Intermediate Similarity	NPC257353
0.764	Intermediate Similarity	NPC324772
0.764	Intermediate Similarity	NPC281880
0.7634	Intermediate Similarity	NPC89747
0.7634	Intermediate Similarity	NPC149224
0.7634	Intermediate Similarity	NPC141292
0.7629	Intermediate Similarity	NPC472932
0.7629	Intermediate Similarity	NPC259286
0.7624	Intermediate Similarity	NPC247957
0.7624	Intermediate Similarity	NPC311612
0.7624	Intermediate Similarity	NPC183570
0.7624	Intermediate Similarity	NPC249187
0.7609	Intermediate Similarity	NPC318390
0.7604	Intermediate Similarity	NPC250575
0.7604	Intermediate Similarity	NPC476304
0.7604	Intermediate Similarity	NPC472930
0.7596	Intermediate Similarity	NPC75389
0.7586	Intermediate Similarity	NPC1973
0.7586	Intermediate Similarity	NPC167873
0.7586	Intermediate Similarity	NPC265588
0.7582	Intermediate Similarity	NPC57370
0.7582	Intermediate Similarity	NPC320548
0.7579	Intermediate Similarity	NPC329596
0.7579	Intermediate Similarity	NPC204188
0.7579	Intermediate Similarity	NPC11216
0.7579	Intermediate Similarity	NPC3345
0.7579	Intermediate Similarity	NPC80561
0.7579	Intermediate Similarity	NPC78973
0.7579	Intermediate Similarity	NPC19771
0.7579	Intermediate Similarity	NPC310479
0.7579	Intermediate Similarity	NPC48010
0.7579	Intermediate Similarity	NPC182136
0.7579	Intermediate Similarity	NPC69622
0.7579	Intermediate Similarity	NPC291484
0.7576	Intermediate Similarity	NPC103051
0.7576	Intermediate Similarity	NPC235464
0.7576	Intermediate Similarity	NPC48647
0.7576	Intermediate Similarity	NPC166745
0.7576	Intermediate Similarity	NPC186810
0.7573	Intermediate Similarity	NPC473284
0.7558	Intermediate Similarity	NPC329090
0.7558	Intermediate Similarity	NPC27395
0.7556	Intermediate Similarity	NPC264245
0.7553	Intermediate Similarity	NPC104560
0.7553	Intermediate Similarity	NPC67872
0.7553	Intermediate Similarity	NPC229612
0.7553	Intermediate Similarity	NPC7280
0.7551	Intermediate Similarity	NPC190713
0.7551	Intermediate Similarity	NPC473153
0.7551	Intermediate Similarity	NPC114743
0.7551	Intermediate Similarity	NPC78473
0.7551	Intermediate Similarity	NPC195366
0.7529	Intermediate Similarity	NPC471272
0.7527	Intermediate Similarity	NPC476043
0.7527	Intermediate Similarity	NPC293287
0.7527	Intermediate Similarity	NPC152808
0.7527	Intermediate Similarity	NPC299068
0.7527	Intermediate Similarity	NPC139724
0.7527	Intermediate Similarity	NPC175145
0.7527	Intermediate Similarity	NPC475069
0.7526	Intermediate Similarity	NPC469406
0.7525	Intermediate Similarity	NPC114540
0.7525	Intermediate Similarity	NPC473424
0.7525	Intermediate Similarity	NPC87351
0.7525	Intermediate Similarity	NPC155332
0.7525	Intermediate Similarity	NPC32577
0.7524	Intermediate Similarity	NPC238850
0.75	Intermediate Similarity	NPC473998
0.75	Intermediate Similarity	NPC227865
0.75	Intermediate Similarity	NPC185568
0.75	Intermediate Similarity	NPC472978
0.75	Intermediate Similarity	NPC33913
0.75	Intermediate Similarity	NPC110923
0.75	Intermediate Similarity	NPC91594
0.75	Intermediate Similarity	NPC74296
0.7476	Intermediate Similarity	NPC295843
0.7475	Intermediate Similarity	NPC161147
0.7475	Intermediate Similarity	NPC291634
0.7475	Intermediate Similarity	NPC120446
0.7474	Intermediate Similarity	NPC472971
0.7474	Intermediate Similarity	NPC1015
0.7474	Intermediate Similarity	NPC2983
0.7474	Intermediate Similarity	NPC473999
0.7474	Intermediate Similarity	NPC309603
0.7474	Intermediate Similarity	NPC472970
0.7474	Intermediate Similarity	NPC31985
0.7474	Intermediate Similarity	NPC470361
0.7473	Intermediate Similarity	NPC201852
0.7453	Intermediate Similarity	NPC284162
0.7453	Intermediate Similarity	NPC255401
0.7451	Intermediate Similarity	NPC297617
0.7451	Intermediate Similarity	NPC171014
0.7451	Intermediate Similarity	NPC280566
0.7451	Intermediate Similarity	NPC72151
0.7451	Intermediate Similarity	NPC85742
0.7451	Intermediate Similarity	NPC111323
0.7449	Intermediate Similarity	NPC276110
0.7449	Intermediate Similarity	NPC88310
0.7449	Intermediate Similarity	NPC271195
0.7447	Intermediate Similarity	NPC287079
0.7447	Intermediate Similarity	NPC470620
0.7444	Intermediate Similarity	NPC241290
0.7444	Intermediate Similarity	NPC164840
0.7444	Intermediate Similarity	NPC96362
0.7444	Intermediate Similarity	NPC236237
0.7444	Intermediate Similarity	NPC471656
0.7444	Intermediate Similarity	NPC234193
0.7444	Intermediate Similarity	NPC322313
0.7444	Intermediate Similarity	NPC102253
0.7444	Intermediate Similarity	NPC209944
0.7442	Intermediate Similarity	NPC68443
0.7431	Intermediate Similarity	NPC474518
0.7429	Intermediate Similarity	NPC214644
0.7426	Intermediate Similarity	NPC163372
0.7426	Intermediate Similarity	NPC302537
0.7423	Intermediate Similarity	NPC38232
0.7423	Intermediate Similarity	NPC474736
0.7423	Intermediate Similarity	NPC53555
0.7423	Intermediate Similarity	NPC69454
0.7419	Intermediate Similarity	NPC470360
0.7419	Intermediate Similarity	NPC274448
0.7419	Intermediate Similarity	NPC179006
0.7419	Intermediate Similarity	NPC471267
0.7419	Intermediate Similarity	NPC474853
0.7419	Intermediate Similarity	NPC266511
0.7404	Intermediate Similarity	NPC330011
0.7404	Intermediate Similarity	NPC220229
0.7404	Intermediate Similarity	NPC185
0.7404	Intermediate Similarity	NPC329048

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 NPC257485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1185
0.2-0.3	3929
0.3-0.4	2707
0.4-0.5	742
0.5-0.6	189
0.6-0.7	213
0.7-0.8	46
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
0.7692	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6931	Approved
0.764	Intermediate Similarity	NPD6930	Phase 2
0.764	Intermediate Similarity	NPD7514	Phase 3
0.7582	Intermediate Similarity	NPD6695	Phase 3
0.7558	Intermediate Similarity	NPD6924	Approved
0.7558	Intermediate Similarity	NPD6926	Approved
0.7528	Intermediate Similarity	NPD6929	Approved
0.7525	Intermediate Similarity	NPD5211	Phase 2
0.7444	Intermediate Similarity	NPD7332	Phase 2
0.7444	Intermediate Similarity	NPD7525	Registered
0.7416	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7145	Approved
0.7386	Intermediate Similarity	NPD6933	Approved
0.7379	Intermediate Similarity	NPD5141	Approved
0.7363	Intermediate Similarity	NPD6902	Approved
0.7327	Intermediate Similarity	NPD5285	Approved
0.7327	Intermediate Similarity	NPD5286	Approved
0.7327	Intermediate Similarity	NPD4696	Approved
0.732	Intermediate Similarity	NPD7637	Suspended
0.7303	Intermediate Similarity	NPD6932	Approved
0.7303	Intermediate Similarity	NPD5776	Phase 2
0.7303	Intermediate Similarity	NPD6925	Approved
0.73	Intermediate Similarity	NPD4755	Approved
0.7273	Intermediate Similarity	NPD8264	Approved
0.7263	Intermediate Similarity	NPD7524	Approved
0.7263	Intermediate Similarity	NPD7750	Discontinued
0.7253	Intermediate Similarity	NPD4820	Approved
0.7253	Intermediate Similarity	NPD7509	Discontinued
0.7253	Intermediate Similarity	NPD4821	Approved
0.7253	Intermediate Similarity	NPD4822	Approved
0.7253	Intermediate Similarity	NPD4819	Approved
0.7245	Intermediate Similarity	NPD4202	Approved
0.7234	Intermediate Similarity	NPD6893	Approved
0.7209	Intermediate Similarity	NPD7144	Approved
0.7209	Intermediate Similarity	NPD7143	Approved
0.7184	Intermediate Similarity	NPD5226	Approved
0.7184	Intermediate Similarity	NPD4633	Approved
0.7184	Intermediate Similarity	NPD5225	Approved
0.7184	Intermediate Similarity	NPD5224	Approved
0.7158	Intermediate Similarity	NPD5279	Phase 3
0.7157	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD6079	Approved
0.7126	Intermediate Similarity	NPD7150	Approved
0.7126	Intermediate Similarity	NPD7151	Approved
0.7126	Intermediate Similarity	NPD7152	Approved
0.7115	Intermediate Similarity	NPD5175	Approved
0.7115	Intermediate Similarity	NPD5174	Approved
0.7113	Intermediate Similarity	NPD5328	Approved
0.7113	Intermediate Similarity	NPD4753	Phase 2
0.7093	Intermediate Similarity	NPD6922	Approved
0.7093	Intermediate Similarity	NPD6923	Approved
0.7087	Intermediate Similarity	NPD5223	Approved
0.7059	Intermediate Similarity	NPD4225	Approved
0.7033	Intermediate Similarity	NPD4268	Approved
0.7033	Intermediate Similarity	NPD4271	Approved
0.703	Intermediate Similarity	NPD4697	Phase 3
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD6899	Approved
0.699	Remote Similarity	NPD7639	Approved
0.699	Remote Similarity	NPD7640	Approved
0.6989	Remote Similarity	NPD6898	Phase 1
0.6981	Remote Similarity	NPD5739	Approved
0.6981	Remote Similarity	NPD7128	Approved
0.6981	Remote Similarity	NPD6675	Approved
0.6981	Remote Similarity	NPD6402	Approved
0.6979	Remote Similarity	NPD3618	Phase 1
0.697	Remote Similarity	NPD7087	Discontinued
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.6957	Remote Similarity	NPD4195	Approved
0.6957	Remote Similarity	NPD6683	Phase 2
0.6947	Remote Similarity	NPD4786	Approved
0.6947	Remote Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD3665	Phase 1
0.6947	Remote Similarity	NPD3666	Approved
0.6931	Remote Similarity	NPD4629	Approved
0.6931	Remote Similarity	NPD5210	Approved
0.6916	Remote Similarity	NPD5697	Approved
0.6907	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7638	Approved
0.6889	Remote Similarity	NPD7339	Approved
0.6889	Remote Similarity	NPD6942	Approved
0.6882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7102	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD1696	Phase 3
0.6863	Remote Similarity	NPD5221	Approved
0.6863	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5222	Approved
0.6852	Remote Similarity	NPD4730	Approved
0.6852	Remote Similarity	NPD7320	Approved
0.6852	Remote Similarity	NPD4729	Approved
0.6848	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5331	Approved
0.6842	Remote Similarity	NPD5362	Discontinued
0.6842	Remote Similarity	NPD5332	Approved
0.6827	Remote Similarity	NPD6648	Approved
0.6822	Remote Similarity	NPD4768	Approved
0.6822	Remote Similarity	NPD4767	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD6649	Approved
0.6818	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6617	Approved
0.6814	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4790	Discontinued
0.6804	Remote Similarity	NPD4694	Approved
0.6804	Remote Similarity	NPD5280	Approved
0.6796	Remote Similarity	NPD6084	Phase 2
0.6796	Remote Similarity	NPD6083	Phase 2
0.6796	Remote Similarity	NPD5173	Approved
0.6792	Remote Similarity	NPD4754	Approved
0.6789	Remote Similarity	NPD6012	Approved
0.6789	Remote Similarity	NPD6013	Approved
0.6789	Remote Similarity	NPD6372	Approved
0.6789	Remote Similarity	NPD6014	Approved
0.6789	Remote Similarity	NPD6373	Approved
0.6778	Remote Similarity	NPD4785	Approved
0.6778	Remote Similarity	NPD4784	Approved
0.6762	Remote Similarity	NPD5344	Discontinued
0.6759	Remote Similarity	NPD5701	Approved
0.6757	Remote Similarity	NPD6882	Approved
0.6757	Remote Similarity	NPD8297	Approved
0.6737	Remote Similarity	NPD3667	Approved
0.6737	Remote Similarity	NPD4221	Approved
0.6737	Remote Similarity	NPD4223	Phase 3
0.6733	Remote Similarity	NPD5778	Approved
0.6733	Remote Similarity	NPD5779	Approved
0.6727	Remote Similarity	NPD5249	Phase 3
0.6727	Remote Similarity	NPD5251	Approved
0.6727	Remote Similarity	NPD5247	Approved
0.6727	Remote Similarity	NPD5250	Approved
0.6727	Remote Similarity	NPD5248	Approved
0.6727	Remote Similarity	NPD4634	Approved
0.6724	Remote Similarity	NPD7503	Approved
0.6702	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5329	Approved
0.6701	Remote Similarity	NPD5363	Approved
0.67	Remote Similarity	NPD5785	Approved
0.6697	Remote Similarity	NPD6011	Approved
0.6697	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6634	Remote Similarity	NPD7515	Phase 2
0.6634	Remote Similarity	NPD6411	Approved
0.6633	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5690	Phase 2
0.6633	Remote Similarity	NPD4623	Approved
0.6633	Remote Similarity	NPD4519	Discontinued
0.6602	Remote Similarity	NPD5695	Phase 3
0.6598	Remote Similarity	NPD4197	Approved
0.6596	Remote Similarity	NPD7645	Phase 2
0.6577	Remote Similarity	NPD5169	Approved
0.6577	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5135	Approved
0.6569	Remote Similarity	NPD6399	Phase 3
0.6562	Remote Similarity	NPD4269	Approved
0.6562	Remote Similarity	NPD4270	Approved
0.6556	Remote Similarity	NPD4243	Approved
0.6535	Remote Similarity	NPD7838	Discovery
0.6535	Remote Similarity	NPD4096	Approved
0.6535	Remote Similarity	NPD7136	Phase 2
0.6526	Remote Similarity	NPD4748	Discontinued
0.6518	Remote Similarity	NPD5127	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7507	Approved
0.6495	Remote Similarity	NPD4788	Approved
0.6484	Remote Similarity	NPD4732	Discontinued
0.6471	Remote Similarity	NPD368	Approved
0.6466	Remote Similarity	NPD7327	Approved
0.6466	Remote Similarity	NPD7328	Approved
0.6465	Remote Similarity	NPD4690	Approved
0.6465	Remote Similarity	NPD4693	Phase 3
0.6465	Remote Similarity	NPD4688	Approved
0.6465	Remote Similarity	NPD5205	Approved
0.6465	Remote Similarity	NPD4138	Approved
0.6465	Remote Similarity	NPD4689	Approved
0.6441	Remote Similarity	NPD8033	Approved
0.6436	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6101	Approved
0.6436	Remote Similarity	NPD6051	Approved
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5696	Approved
0.641	Remote Similarity	NPD7516	Approved
0.641	Remote Similarity	NPD7100	Approved
0.641	Remote Similarity	NPD7101	Approved
0.6404	Remote Similarity	NPD4632	Approved
0.64	Remote Similarity	NPD4250	Approved
0.64	Remote Similarity	NPD4251	Approved
0.6389	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8377	Approved
0.6356	Remote Similarity	NPD6054	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