NPASS Compound

Structure

NPC476478 OpenBabel07101718292D 41 43 0 0 1 0 0 0 0 0999 V2000 1.0318 -0.1989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1811 0.7286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4873 -0.3992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3160 -2.7675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 -2.9112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6241 0.4127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1109 -2.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0383 -2.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3284 0.8674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5414 -0.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 -0.6626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5746 -0.7205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5746 0.1687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2286 -0.6626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 1.1924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3490 -1.3163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8894 -2.0384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1982 -2.5723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9688 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1492 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 -1.5901 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5746 -0.1989 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0354 -0.4986 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6266 -1.0454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1138 -0.4986 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2286 -1.5901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4774 -1.0454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3922 -0.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5746 -2.0538 0.0000 C 0 0 0 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 -1.3778 2.1198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7993 -2.4729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8074 -2.1704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9234 -3.1506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8868 -0.5803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2358 -0.0673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5746 0.7286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4857 -1.6552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5447 -1.1774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3365 -1.6552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3954 -1.1774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 29 1 0 0 0 0 8 29 1 0 0 0 0 10 20 2 0 0 0 0 10 24 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 30 1 0 0 0 0 14 22 1 0 0 0 0 14 26 2 0 0 0 0 15 31 2 0 0 0 0 15 37 1 0 0 0 0 16 32 2 0 0 0 0 16 38 1 0 0 0 0 17 33 2 0 0 0 0 17 39 1 0 0 0 0 18 34 2 0 0 0 0 18 40 1 0 0 0 0 19 35 2 0 0 0 0 19 41 1 0 0 0 0 20 23 1 0 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 21 29 1 0 0 0 0 22 37 1 6 0 0 0 23 38 1 6 0 0 0 24 39 1 1 0 0 0 25 30 1 1 0 0 0 25 40 1 0 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 27 41 1 6 0 0 0 28 30 1 0 0 0 0 28 36 2 0 0 0 0 30 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.26
Volume:	577.367
LogP:	3.199
LogD:	2.395
LogS:	-4.44
# Rotatable Bonds:	10
TPSA:	148.57
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	6.515
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	0.0001314813271164894
Pgp-inhibitor:	1.0
Pgp-substrate:	0.142
Human Intestinal Absorption (HIA):	0.116
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.36
Plasma Protein Binding (PPB):	77.04132843017578%
Volume Distribution (VD):	1.405
Pgp-substrate:	12.128039360046387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.487
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.56
CYP3A4-substrate:	0.471

ADMET: Excretion

Clearance (CL):	2.589
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.907
Drug-inuced Liver Injury (DILI):	0.896
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.349
Carcinogencity:	0.063
Eye Corrosion:	0.007
Eye Irritation:	0.023
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC476478

Natural Product ID:	NPC476478
*Common Name:**	XMDHIHGBHFVDPF-LXOVCLPSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XMDHIHGBHFVDPF-LXOVCLPSSA-N
Standard InCHI:	InChI=1S/C30H40O11/c1-14-22(37-15(2)31)11-21-24(39-17(4)33)10-20-13-30(9,25(40-18(5)34)12-23(20)38-16(3)32)28(36)27(41-19(6)35)26(14)29(21,7)8/h10,21-25,27H,11-13H2,1-9H3/b20-10+/t21-,22-,23-,24-,25-,27+,30-/m0/s1
SMILES:	CC1=C2C(C(=O)C3(CC(=CC(C(C2(C)C)CC1OC(=O)C)OC(=O)C)C(CC3OC(=O)C)OC(=O)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL96121
PubChem CID:	44326842
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2
Others	2

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[520918]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	5.0	%	PMID[520918]
NPT1178	Cell Line	KB 3-1	Homo sapiens	Inhibition	=	22.0	%	PMID[520918]

☑ 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 NPC476478 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	240
0.1-0.2	1462
0.2-0.3	5056
0.3-0.4	8822
0.4-0.5	14463
0.5-0.6	7529
0.6-0.7	4707
0.7-0.8	412
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC123726
0.9388	High Similarity	NPC284365
0.8824	High Similarity	NPC476479
0.8365	Intermediate Similarity	NPC475587
0.8365	Intermediate Similarity	NPC475510
0.8317	Intermediate Similarity	NPC476933
0.8286	Intermediate Similarity	NPC473939
0.8286	Intermediate Similarity	NPC473595
0.8252	Intermediate Similarity	NPC474166
0.8252	Intermediate Similarity	NPC19239
0.8218	Intermediate Similarity	NPC264378
0.8182	Intermediate Similarity	NPC148463
0.8163	Intermediate Similarity	NPC473944
0.8131	Intermediate Similarity	NPC473843
0.8131	Intermediate Similarity	NPC473594
0.8131	Intermediate Similarity	NPC474586
0.8131	Intermediate Similarity	NPC281624
0.8131	Intermediate Similarity	NPC473975
0.8073	Intermediate Similarity	NPC159333
0.8056	Intermediate Similarity	NPC194619
0.8037	Intermediate Similarity	NPC42662
0.8021	Intermediate Similarity	NPC220478
0.7982	Intermediate Similarity	NPC473877
0.7961	Intermediate Similarity	NPC469551
0.7944	Intermediate Similarity	NPC322903
0.7928	Intermediate Similarity	NPC477509
0.7921	Intermediate Similarity	NPC217329
0.7913	Intermediate Similarity	NPC105926
0.7913	Intermediate Similarity	NPC91693
0.7913	Intermediate Similarity	NPC265557
0.7913	Intermediate Similarity	NPC18945
0.7909	Intermediate Similarity	NPC470120
0.79	Intermediate Similarity	NPC476598
0.79	Intermediate Similarity	NPC476597
0.787	Intermediate Similarity	NPC475922
0.7857	Intermediate Similarity	NPC69713
0.7857	Intermediate Similarity	NPC473590
0.785	Intermediate Similarity	NPC474716
0.7845	Intermediate Similarity	NPC476729
0.783	Intermediate Similarity	NPC470297
0.7826	Intermediate Similarity	NPC312833
0.7822	Intermediate Similarity	NPC476596
0.7822	Intermediate Similarity	NPC470697
0.7818	Intermediate Similarity	NPC317687
0.781	Intermediate Similarity	NPC183571
0.7798	Intermediate Similarity	NPC161816
0.7798	Intermediate Similarity	NPC115257
0.7788	Intermediate Similarity	NPC174314
0.7768	Intermediate Similarity	NPC270478
0.7768	Intermediate Similarity	NPC476711
0.7768	Intermediate Similarity	NPC476710
0.7768	Intermediate Similarity	NPC474333
0.7767	Intermediate Similarity	NPC285513
0.7759	Intermediate Similarity	NPC67251
0.7757	Intermediate Similarity	NPC1679
0.7757	Intermediate Similarity	NPC111952
0.7757	Intermediate Similarity	NPC475571
0.7755	Intermediate Similarity	NPC102640
0.7748	Intermediate Similarity	NPC33360
0.7748	Intermediate Similarity	NPC471204
0.7748	Intermediate Similarity	NPC472926
0.7745	Intermediate Similarity	NPC37603
0.7745	Intermediate Similarity	NPC471786
0.7739	Intermediate Similarity	NPC470779
0.7736	Intermediate Similarity	NPC69171
0.7736	Intermediate Similarity	NPC254202
0.7736	Intermediate Similarity	NPC474165
0.7727	Intermediate Similarity	NPC317107
0.7719	Intermediate Similarity	NPC470186
0.7708	Intermediate Similarity	NPC222358
0.7699	Intermediate Similarity	NPC476712
0.7699	Intermediate Similarity	NPC476713
0.7699	Intermediate Similarity	NPC296822
0.7692	Intermediate Similarity	NPC470188
0.7692	Intermediate Similarity	NPC24651
0.7692	Intermediate Similarity	NPC470922
0.7685	Intermediate Similarity	NPC251824
0.7685	Intermediate Similarity	NPC86852
0.7685	Intermediate Similarity	NPC112780
0.7685	Intermediate Similarity	NPC143609
0.767	Intermediate Similarity	NPC202833
0.7664	Intermediate Similarity	NPC258532
0.7658	Intermediate Similarity	NPC90952
0.7658	Intermediate Similarity	NPC277769
0.7658	Intermediate Similarity	NPC471933
0.7653	Intermediate Similarity	NPC102996
0.7652	Intermediate Similarity	NPC109607
0.7652	Intermediate Similarity	NPC107338
0.7647	Intermediate Similarity	NPC477439
0.7642	Intermediate Similarity	NPC162973
0.7642	Intermediate Similarity	NPC475091
0.7642	Intermediate Similarity	NPC474709
0.7636	Intermediate Similarity	NPC253906
0.7632	Intermediate Similarity	NPC21326
0.7632	Intermediate Similarity	NPC470776
0.7632	Intermediate Similarity	NPC251310
0.7629	Intermediate Similarity	NPC474359
0.7627	Intermediate Similarity	NPC181999
0.7619	Intermediate Similarity	NPC474718
0.7619	Intermediate Similarity	NPC306856
0.7619	Intermediate Similarity	NPC472972
0.7619	Intermediate Similarity	NPC471413
0.7619	Intermediate Similarity	NPC54705
0.7615	Intermediate Similarity	NPC94377
0.7615	Intermediate Similarity	NPC89171
0.7615	Intermediate Similarity	NPC476802
0.7611	Intermediate Similarity	NPC474734
0.76	Intermediate Similarity	NPC475971
0.76	Intermediate Similarity	NPC284561
0.7596	Intermediate Similarity	NPC254496
0.7593	Intermediate Similarity	NPC16313
0.7593	Intermediate Similarity	NPC28791
0.7593	Intermediate Similarity	NPC475802
0.7593	Intermediate Similarity	NPC9303
0.7593	Intermediate Similarity	NPC295366
0.7593	Intermediate Similarity	NPC470975
0.7593	Intermediate Similarity	NPC103088
0.7593	Intermediate Similarity	NPC470979
0.7589	Intermediate Similarity	NPC7921
0.7589	Intermediate Similarity	NPC208998
0.7573	Intermediate Similarity	NPC477437
0.7573	Intermediate Similarity	NPC266899
0.7573	Intermediate Similarity	NPC477438
0.757	Intermediate Similarity	NPC471365
0.757	Intermediate Similarity	NPC471364
0.757	Intermediate Similarity	NPC132395
0.757	Intermediate Similarity	NPC4620
0.7568	Intermediate Similarity	NPC34315
0.7568	Intermediate Similarity	NPC171888
0.7568	Intermediate Similarity	NPC146945
0.7565	Intermediate Similarity	NPC472933
0.7565	Intermediate Similarity	NPC476529
0.7565	Intermediate Similarity	NPC475775
0.7547	Intermediate Similarity	NPC471412
0.7547	Intermediate Similarity	NPC472643
0.7547	Intermediate Similarity	NPC111292
0.7545	Intermediate Similarity	NPC474243
0.7545	Intermediate Similarity	NPC471934
0.7545	Intermediate Similarity	NPC469370
0.7545	Intermediate Similarity	NPC474242
0.7544	Intermediate Similarity	NPC470775
0.7544	Intermediate Similarity	NPC134430
0.7544	Intermediate Similarity	NPC472927
0.7544	Intermediate Similarity	NPC176513
0.7525	Intermediate Similarity	NPC471818
0.7525	Intermediate Similarity	NPC161638
0.7524	Intermediate Similarity	NPC476800
0.7524	Intermediate Similarity	NPC216478
0.7524	Intermediate Similarity	NPC472186
0.7524	Intermediate Similarity	NPC471366
0.7524	Intermediate Similarity	NPC471932
0.7524	Intermediate Similarity	NPC318917
0.7523	Intermediate Similarity	NPC176949
0.7523	Intermediate Similarity	NPC72813
0.7523	Intermediate Similarity	NPC324327
0.7523	Intermediate Similarity	NPC194620
0.7523	Intermediate Similarity	NPC469558
0.7523	Intermediate Similarity	NPC201908
0.7523	Intermediate Similarity	NPC326994
0.7523	Intermediate Similarity	NPC474421
0.7522	Intermediate Similarity	NPC469877
0.7522	Intermediate Similarity	NPC473798
0.7522	Intermediate Similarity	NPC470919
0.75	Intermediate Similarity	NPC477127
0.75	Intermediate Similarity	NPC472004
0.75	Intermediate Similarity	NPC4573
0.75	Intermediate Similarity	NPC239162
0.75	Intermediate Similarity	NPC475036
0.75	Intermediate Similarity	NPC220964
0.75	Intermediate Similarity	NPC477128
0.75	Intermediate Similarity	NPC269530
0.75	Intermediate Similarity	NPC475676
0.75	Intermediate Similarity	NPC184065
0.7478	Intermediate Similarity	NPC240509
0.7478	Intermediate Similarity	NPC17772
0.7478	Intermediate Similarity	NPC470420
0.7478	Intermediate Similarity	NPC297179
0.7477	Intermediate Similarity	NPC476081
0.7477	Intermediate Similarity	NPC49393
0.7477	Intermediate Similarity	NPC105725
0.7477	Intermediate Similarity	NPC83005
0.7477	Intermediate Similarity	NPC5103
0.7477	Intermediate Similarity	NPC80781
0.7477	Intermediate Similarity	NPC478156
0.7476	Intermediate Similarity	NPC473434
0.7476	Intermediate Similarity	NPC250075
0.7476	Intermediate Similarity	NPC471446
0.7476	Intermediate Similarity	NPC161998
0.7476	Intermediate Similarity	NPC474841
0.7458	Intermediate Similarity	NPC472399
0.7456	Intermediate Similarity	NPC213084
0.7456	Intermediate Similarity	NPC328374
0.7456	Intermediate Similarity	NPC470628
0.7456	Intermediate Similarity	NPC190185
0.7456	Intermediate Similarity	NPC251236
0.7456	Intermediate Similarity	NPC40632
0.7456	Intermediate Similarity	NPC474046
0.7456	Intermediate Similarity	NPC96312
0.7456	Intermediate Similarity	NPC259306
0.7455	Intermediate Similarity	NPC233379

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 NPC476478 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1924
0.2-0.3	3824
0.3-0.4	2011
0.4-0.5	808
0.5-0.6	252
0.6-0.7	120
0.7-0.8	1
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
0.7455	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5739	Approved
0.7273	Intermediate Similarity	NPD7128	Approved
0.7273	Intermediate Similarity	NPD6675	Approved
0.7273	Intermediate Similarity	NPD6402	Approved
0.7232	Intermediate Similarity	NPD6372	Approved
0.7232	Intermediate Similarity	NPD6373	Approved
0.7203	Intermediate Similarity	NPD6319	Approved
0.7167	Intermediate Similarity	NPD8328	Phase 3
0.7157	Intermediate Similarity	NPD5737	Approved
0.7157	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD7320	Approved
0.7105	Intermediate Similarity	NPD6649	Approved
0.7105	Intermediate Similarity	NPD6650	Approved
0.7054	Intermediate Similarity	NPD5697	Approved
0.7054	Intermediate Similarity	NPD5701	Approved
0.7054	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5779	Approved
0.7048	Intermediate Similarity	NPD5778	Approved
0.7043	Intermediate Similarity	NPD6882	Approved
0.7043	Intermediate Similarity	NPD8297	Approved
0.7037	Intermediate Similarity	NPD7638	Approved
0.7018	Intermediate Similarity	NPD6883	Approved
0.7018	Intermediate Similarity	NPD7102	Approved
0.7018	Intermediate Similarity	NPD7290	Approved
0.6981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7900	Approved
0.6972	Remote Similarity	NPD7639	Approved
0.6972	Remote Similarity	NPD7640	Approved
0.6967	Remote Similarity	NPD7492	Approved
0.6964	Remote Similarity	NPD6008	Approved
0.6957	Remote Similarity	NPD6869	Approved
0.6957	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD8130	Phase 1
0.6957	Remote Similarity	NPD6847	Approved
0.6952	Remote Similarity	NPD5693	Phase 1
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6013	Approved
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6012	Approved
0.6917	Remote Similarity	NPD6054	Approved
0.6917	Remote Similarity	NPD6059	Approved
0.6911	Remote Similarity	NPD6616	Approved
0.69	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6399	Phase 3
0.688	Remote Similarity	NPD7319	Approved
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1694	Approved
0.686	Remote Similarity	NPD6921	Approved
0.6855	Remote Similarity	NPD8293	Discontinued
0.6855	Remote Similarity	NPD7078	Approved
0.6842	Remote Similarity	NPD6686	Approved
0.6842	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD7748	Approved
0.681	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6796	Remote Similarity	NPD7521	Approved
0.6796	Remote Similarity	NPD6098	Approved
0.6796	Remote Similarity	NPD6684	Approved
0.6796	Remote Similarity	NPD6409	Approved
0.6796	Remote Similarity	NPD7334	Approved
0.6796	Remote Similarity	NPD7146	Approved
0.6796	Remote Similarity	NPD5330	Approved
0.6792	Remote Similarity	NPD7983	Approved
0.6792	Remote Similarity	NPD6411	Approved
0.6789	Remote Similarity	NPD7902	Approved
0.6789	Remote Similarity	NPD6083	Phase 2
0.6789	Remote Similarity	NPD6084	Phase 2
0.6783	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6904	Approved
0.6762	Remote Similarity	NPD6673	Approved
0.6762	Remote Similarity	NPD6080	Approved
0.6759	Remote Similarity	NPD5695	Phase 3
0.6731	Remote Similarity	NPD3573	Approved
0.6721	Remote Similarity	NPD6016	Approved
0.6721	Remote Similarity	NPD6015	Approved
0.6701	Remote Similarity	NPD8039	Approved
0.6698	Remote Similarity	NPD6698	Approved
0.6698	Remote Similarity	NPD46	Approved
0.6695	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.664	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD4755	Approved
0.6636	Remote Similarity	NPD6050	Approved
0.6613	Remote Similarity	NPD7604	Phase 2
0.661	Remote Similarity	NPD6053	Discontinued
0.6604	Remote Similarity	NPD6101	Approved
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8515	Approved
0.6585	Remote Similarity	NPD8513	Phase 3
0.6585	Remote Similarity	NPD5983	Phase 2
0.6585	Remote Similarity	NPD8516	Approved
0.6585	Remote Similarity	NPD8517	Approved
0.6583	Remote Similarity	NPD6274	Approved
0.6581	Remote Similarity	NPD4634	Approved
0.6577	Remote Similarity	NPD5696	Approved
0.6577	Remote Similarity	NPD4225	Approved
0.6557	Remote Similarity	NPD7101	Approved
0.6557	Remote Similarity	NPD7100	Approved
0.6549	Remote Similarity	NPD5211	Phase 2
0.6542	Remote Similarity	NPD5692	Phase 3
0.6538	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4700	Approved
0.6518	Remote Similarity	NPD5285	Approved
0.6518	Remote Similarity	NPD4696	Approved
0.6518	Remote Similarity	NPD5286	Approved
0.6512	Remote Similarity	NPD7260	Phase 2
0.6508	Remote Similarity	NPD6336	Discontinued
0.6496	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5694	Approved
0.6475	Remote Similarity	NPD6335	Approved
0.6466	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6908	Approved
0.6452	Remote Similarity	NPD6909	Approved
0.6449	Remote Similarity	NPD5328	Approved
0.6449	Remote Similarity	NPD6051	Approved
0.6446	Remote Similarity	NPD6868	Approved
0.6435	Remote Similarity	NPD5141	Approved
0.6406	Remote Similarity	NPD6033	Approved
0.6404	Remote Similarity	NPD5224	Approved
0.6404	Remote Similarity	NPD4633	Approved
0.6404	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD7632	Discontinued
0.6404	Remote Similarity	NPD5226	Approved
0.6396	Remote Similarity	NPD5222	Approved
0.6396	Remote Similarity	NPD5221	Approved
0.6396	Remote Similarity	NPD4697	Phase 3
0.6396	Remote Similarity	NPD7839	Suspended
0.6396	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6317	Approved
0.6379	Remote Similarity	NPD4767	Approved
0.6379	Remote Similarity	NPD4768	Approved
0.6364	Remote Similarity	NPD5282	Discontinued
0.6348	Remote Similarity	NPD5175	Approved
0.6348	Remote Similarity	NPD5174	Approved
0.6341	Remote Similarity	NPD6314	Approved
0.6341	Remote Similarity	NPD6313	Approved
0.6339	Remote Similarity	NPD5173	Approved
0.633	Remote Similarity	NPD6079	Approved
0.6328	Remote Similarity	NPD8074	Phase 3
0.6325	Remote Similarity	NPD6412	Phase 2
0.6316	Remote Similarity	NPD5223	Approved
0.6306	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6371	Approved
0.6286	Remote Similarity	NPD4786	Approved
0.6286	Remote Similarity	NPD3668	Phase 3
0.6271	Remote Similarity	NPD4730	Approved
0.6271	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD5209	Approved
0.625	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD3667	Approved
0.6239	Remote Similarity	NPD5785	Approved
0.6228	Remote Similarity	NPD6648	Approved
0.6212	Remote Similarity	NPD6845	Suspended
0.621	Remote Similarity	NPD7328	Approved
0.621	Remote Similarity	NPD7327	Approved
0.6207	Remote Similarity	NPD4754	Approved
0.6182	Remote Similarity	NPD8034	Phase 2
0.6182	Remote Similarity	NPD8035	Phase 2
0.6174	Remote Similarity	NPD5344	Discontinued
0.6168	Remote Similarity	NPD3618	Phase 1
0.6168	Remote Similarity	NPD5786	Approved
0.6167	Remote Similarity	NPD5250	Approved
0.6167	Remote Similarity	NPD5249	Phase 3
0.6167	Remote Similarity	NPD5248	Approved
0.6167	Remote Similarity	NPD5251	Approved
0.6167	Remote Similarity	NPD5247	Approved
0.6161	Remote Similarity	NPD5654	Approved
0.616	Remote Similarity	NPD7516	Approved
0.6148	Remote Similarity	NPD8133	Approved
0.6147	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4753	Phase 2
0.6134	Remote Similarity	NPD5128	Approved
0.6116	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD6334	Approved
0.6103	Remote Similarity	NPD6333	Approved
0.6074	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8296	Approved
0.6063	Remote Similarity	NPD8380	Approved
0.6063	Remote Similarity	NPD8335	Approved
0.6063	Remote Similarity	NPD8379	Approved
0.6063	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8378	Approved
0.6058	Remote Similarity	NPD5368	Approved
0.6058	Remote Similarity	NPD4695	Discontinued
0.6055	Remote Similarity	NPD5208	Approved
0.6053	Remote Similarity	NPD5959	Approved
0.6019	Remote Similarity	NPD6422	Discontinued
0.6019	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD5784	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