NPASS Compound

Structure

NPC473440 OpenBabel07101718282D 41 45 0 0 1 0 0 0 0 0999 V2000 0.7206 0.6978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -3.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6037 0.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1970 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8605 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6947 -0.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1670 0.2372 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8364 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1454 -0.4826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.4067 -2.6456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7681 -0.8893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 2.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 2 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 31 1 0 0 0 0 17 24 1 0 0 0 0 18 24 1 0 0 0 0 18 32 1 6 0 0 0 19 25 1 0 0 0 0 19 33 1 0 0 0 0 20 34 2 0 0 0 0 20 39 1 0 0 0 0 21 35 2 0 0 0 0 21 40 1 0 0 0 0 23 17 1 6 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 36 2 0 0 0 0 25 41 1 6 0 0 0 26 37 2 0 0 0 0 26 41 1 0 0 0 0 27 29 1 0 0 0 0 27 31 1 6 0 0 0 27 38 1 0 0 0 0 28 33 1 6 0 0 0 28 39 1 0 0 0 0 29 32 1 1 0 0 0 29 40 1 0 0 0 0 30 32 1 0 0 0 0 31 33 1 1 0 0 0 32 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	564.27
Volume:	583.135
LogP:	3.239
LogD:	2.146
LogS:	-4.983
# Rotatable Bonds:	8
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	6.538
Fsp3:	0.576
Lipinski Rule-of-5:	Accepted
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:	-5.214
MDCK Permeability:	2.795286854961887e-05
Pgp-inhibitor:	0.762
Pgp-substrate:	0.746
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	65.96578979492188%
Volume Distribution (VD):	1.602
Pgp-substrate:	25.050800323486328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.191
CYP2C19-substrate:	0.157
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.296
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.78
CYP3A4-substrate:	0.541

ADMET: Excretion

Clearance (CL):	4.613
Half-life (T1/2):	0.188

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.598
Drug-inuced Liver Injury (DILI):	0.851
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.778
Skin Sensitization:	0.685
Carcinogencity:	0.115
Eye Corrosion:	0.004
Eye Irritation:	0.036
Respiratory Toxicity:	0.232

Download Data

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

Natural Product: NPC473440

Natural Product ID:	NPC473440
*Common Name:**	BFWCKYWHUBGMKI-GMCBVFIXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BFWCKYWHUBGMKI-GMCBVFIXSA-N
Standard InCHI:	InChI=1S/C33H40O8/c1-18-24(36)17-23-28(39-20(3)34)33-19(2)25(41-26(37)14-13-22-11-9-8-10-12-22)15-16-31(33,7)27(38)29(40-21(4)35)32(18,33)30(23,5)6/h8-14,18,23,25,27-29,38H,2,15-17H2,1,3-7H3/b14-13+/t18-,23+,25+,27+,28-,29+,31+,32-,33?/m1/s1
SMILES:	CC1C(=O)CC2C(C34C1(C2(C)C)C(C(C3(CCC(C4=C)OC(=O)C=CC5=CC=CC=C5)C)O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL433401
PubChem CID:	44327128
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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	=	6.4	ug ml-1	PMID[486901]
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	=	6.1	ug ml-1	PMID[486901]
NPT27	Others	Unspecified		ED50	=	7.7	ug ml-1	PMID[486901]

☑ 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 NPC473440 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	291
0.1-0.2	950
0.2-0.3	2181
0.3-0.4	4532
0.4-0.5	8073
0.5-0.6	17721
0.6-0.7	7437
0.7-0.8	1320
0.8-0.85	177
0.85-0.9	10
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC4242
0.9618	High Similarity	NPC471911
0.9412	High Similarity	NPC63737
0.913	High Similarity	NPC475135
0.8881	High Similarity	NPC473443
0.8806	High Similarity	NPC225103
0.8797	High Similarity	NPC473423
0.8741	High Similarity	NPC472388
0.8613	High Similarity	NPC80599
0.8613	High Similarity	NPC209851
0.8542	High Similarity	NPC277053
0.8542	High Similarity	NPC301946
0.8472	Intermediate Similarity	NPC80895
0.8472	Intermediate Similarity	NPC471912
0.8467	Intermediate Similarity	NPC475138
0.8433	Intermediate Similarity	NPC469742
0.84	Intermediate Similarity	NPC70344
0.8366	Intermediate Similarity	NPC165234
0.8366	Intermediate Similarity	NPC475536
0.8366	Intermediate Similarity	NPC55744
0.8356	Intermediate Similarity	NPC478263
0.8333	Intermediate Similarity	NPC469456
0.8333	Intermediate Similarity	NPC471176
0.8321	Intermediate Similarity	NPC195224
0.8312	Intermediate Similarity	NPC475300
0.8312	Intermediate Similarity	NPC473797
0.8312	Intermediate Similarity	NPC473641
0.8312	Intermediate Similarity	NPC475505
0.8312	Intermediate Similarity	NPC475464
0.8312	Intermediate Similarity	NPC475437
0.8299	Intermediate Similarity	NPC205389
0.8298	Intermediate Similarity	NPC477896
0.8298	Intermediate Similarity	NPC477893
0.8288	Intermediate Similarity	NPC471162
0.8288	Intermediate Similarity	NPC478264
0.8273	Intermediate Similarity	NPC72915
0.8273	Intermediate Similarity	NPC472361
0.8264	Intermediate Similarity	NPC325078
0.8252	Intermediate Similarity	NPC473301
0.8231	Intermediate Similarity	NPC473602
0.8231	Intermediate Similarity	NPC312393
0.8227	Intermediate Similarity	NPC203486
0.8227	Intermediate Similarity	NPC126516
0.8227	Intermediate Similarity	NPC48929
0.8227	Intermediate Similarity	NPC329913
0.8222	Intermediate Similarity	NPC12016
0.8214	Intermediate Similarity	NPC475493
0.8207	Intermediate Similarity	NPC182869
0.8207	Intermediate Similarity	NPC140021
0.8205	Intermediate Similarity	NPC477491
0.8194	Intermediate Similarity	NPC79921
0.8188	Intermediate Similarity	NPC7095
0.8188	Intermediate Similarity	NPC25484
0.8188	Intermediate Similarity	NPC232583
0.8188	Intermediate Similarity	NPC125033
0.8182	Intermediate Similarity	NPC184109
0.8176	Intermediate Similarity	NPC327031
0.8169	Intermediate Similarity	NPC200154
0.8163	Intermediate Similarity	NPC127857
0.8162	Intermediate Similarity	NPC472373
0.8156	Intermediate Similarity	NPC159811
0.8156	Intermediate Similarity	NPC472437
0.8156	Intermediate Similarity	NPC472248
0.8151	Intermediate Similarity	NPC95449
0.8151	Intermediate Similarity	NPC477894
0.8151	Intermediate Similarity	NPC45307
0.8146	Intermediate Similarity	NPC472657
0.8146	Intermediate Similarity	NPC472658
0.8146	Intermediate Similarity	NPC471135
0.8143	Intermediate Similarity	NPC472418
0.8138	Intermediate Similarity	NPC242355
0.8138	Intermediate Similarity	NPC118080
0.8138	Intermediate Similarity	NPC16912
0.8138	Intermediate Similarity	NPC291599
0.8138	Intermediate Similarity	NPC472576
0.8138	Intermediate Similarity	NPC87448
0.8138	Intermediate Similarity	NPC27377
0.8138	Intermediate Similarity	NPC97947
0.8138	Intermediate Similarity	NPC41481
0.8133	Intermediate Similarity	NPC471103
0.8133	Intermediate Similarity	NPC51602
0.8121	Intermediate Similarity	NPC81698
0.8121	Intermediate Similarity	NPC76103
0.8121	Intermediate Similarity	NPC60509
0.8121	Intermediate Similarity	NPC250046
0.8116	Intermediate Similarity	NPC190849
0.8116	Intermediate Similarity	NPC171007
0.8116	Intermediate Similarity	NPC476971
0.8116	Intermediate Similarity	NPC476972
0.8112	Intermediate Similarity	NPC472372
0.8112	Intermediate Similarity	NPC472374
0.8105	Intermediate Similarity	NPC318447
0.8105	Intermediate Similarity	NPC322048
0.8102	Intermediate Similarity	NPC471758
0.8099	Intermediate Similarity	NPC28836
0.8099	Intermediate Similarity	NPC311492
0.8092	Intermediate Similarity	NPC473611
0.8092	Intermediate Similarity	NPC473632
0.8092	Intermediate Similarity	NPC132599
0.8092	Intermediate Similarity	NPC469730
0.8092	Intermediate Similarity	NPC21410
0.8092	Intermediate Similarity	NPC473670
0.8085	Intermediate Similarity	NPC476976
0.8085	Intermediate Similarity	NPC233860
0.8085	Intermediate Similarity	NPC472394
0.8085	Intermediate Similarity	NPC239358
0.8082	Intermediate Similarity	NPC192658
0.8079	Intermediate Similarity	NPC472548
0.8079	Intermediate Similarity	NPC477905
0.8069	Intermediate Similarity	NPC171207
0.8069	Intermediate Similarity	NPC97667
0.8069	Intermediate Similarity	NPC100913
0.8069	Intermediate Similarity	NPC472547
0.8069	Intermediate Similarity	NPC275592
0.8069	Intermediate Similarity	NPC90614
0.8069	Intermediate Similarity	NPC475660
0.8067	Intermediate Similarity	NPC476173
0.8067	Intermediate Similarity	NPC161239
0.8067	Intermediate Similarity	NPC198455
0.8067	Intermediate Similarity	NPC165260
0.8067	Intermediate Similarity	NPC475417
0.8067	Intermediate Similarity	NPC112216
0.8067	Intermediate Similarity	NPC475561
0.8058	Intermediate Similarity	NPC58061
0.8056	Intermediate Similarity	NPC27721
0.8056	Intermediate Similarity	NPC262324
0.8052	Intermediate Similarity	NPC476784
0.805	Intermediate Similarity	NPC477488
0.8043	Intermediate Similarity	NPC475933
0.8043	Intermediate Similarity	NPC473082
0.8043	Intermediate Similarity	NPC470158
0.8043	Intermediate Similarity	NPC476970
0.8043	Intermediate Similarity	NPC477366
0.8043	Intermediate Similarity	NPC45821
0.8042	Intermediate Similarity	NPC471864
0.8041	Intermediate Similarity	NPC29704
0.8041	Intermediate Similarity	NPC472568
0.8041	Intermediate Similarity	NPC158663
0.8041	Intermediate Similarity	NPC171525
0.8041	Intermediate Similarity	NPC200471
0.8041	Intermediate Similarity	NPC470157
0.8041	Intermediate Similarity	NPC184817
0.8041	Intermediate Similarity	NPC473088
0.8041	Intermediate Similarity	NPC70403
0.8041	Intermediate Similarity	NPC476973
0.8041	Intermediate Similarity	NPC469349
0.8041	Intermediate Similarity	NPC470159
0.8041	Intermediate Similarity	NPC472556
0.8041	Intermediate Similarity	NPC472571
0.8041	Intermediate Similarity	NPC177940
0.8041	Intermediate Similarity	NPC471104
0.8041	Intermediate Similarity	NPC96903
0.8041	Intermediate Similarity	NPC174982
0.8041	Intermediate Similarity	NPC472572
0.8041	Intermediate Similarity	NPC472575
0.8039	Intermediate Similarity	NPC106895
0.8039	Intermediate Similarity	NPC475548
0.8039	Intermediate Similarity	NPC475638
0.8039	Intermediate Similarity	NPC323001
0.8039	Intermediate Similarity	NPC290683
0.8039	Intermediate Similarity	NPC326235
0.8029	Intermediate Similarity	NPC12881
0.8029	Intermediate Similarity	NPC140118
0.8028	Intermediate Similarity	NPC15850
0.8027	Intermediate Similarity	NPC191387
0.8027	Intermediate Similarity	NPC131966
0.8026	Intermediate Similarity	NPC242262
0.8026	Intermediate Similarity	NPC158333
0.8026	Intermediate Similarity	NPC249471
0.8026	Intermediate Similarity	NPC237549
0.8026	Intermediate Similarity	NPC472005
0.8026	Intermediate Similarity	NPC265395
0.8026	Intermediate Similarity	NPC473414
0.8026	Intermediate Similarity	NPC472022
0.8026	Intermediate Similarity	NPC257213
0.8026	Intermediate Similarity	NPC477100
0.8026	Intermediate Similarity	NPC256142
0.8026	Intermediate Similarity	NPC1173
0.8026	Intermediate Similarity	NPC304876
0.8026	Intermediate Similarity	NPC472030
0.8026	Intermediate Similarity	NPC477098
0.8014	Intermediate Similarity	NPC476977
0.8014	Intermediate Similarity	NPC266374
0.8014	Intermediate Similarity	NPC474303
0.8014	Intermediate Similarity	NPC473497
0.8014	Intermediate Similarity	NPC475413
0.8013	Intermediate Similarity	NPC96308
0.8013	Intermediate Similarity	NPC62792
0.8	Intermediate Similarity	NPC309991
0.8	Intermediate Similarity	NPC326328
0.8	Intermediate Similarity	NPC323356
0.8	Intermediate Similarity	NPC471138
0.7987	Intermediate Similarity	NPC240115
0.7987	Intermediate Similarity	NPC40138
0.7987	Intermediate Similarity	NPC170668
0.7986	Intermediate Similarity	NPC285221
0.7986	Intermediate Similarity	NPC202729
0.7986	Intermediate Similarity	NPC477365
0.7986	Intermediate Similarity	NPC194769
0.7974	Intermediate Similarity	NPC228204

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 NPC473440 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	636
0.2-0.3	1523
0.3-0.4	3154
0.4-0.5	2212
0.5-0.6	1055
0.6-0.7	310
0.7-0.8	18
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8041	Intermediate Similarity	NPD7236	Approved
0.8	Intermediate Similarity	NPD7799	Discontinued
0.7895	Intermediate Similarity	NPD7239	Suspended
0.7669	Intermediate Similarity	NPD7094	Approved
0.7669	Intermediate Similarity	NPD6858	Approved
0.7655	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7961	Discontinued
0.7466	Intermediate Similarity	NPD6663	Approved
0.7438	Intermediate Similarity	NPD7058	Phase 2
0.7438	Intermediate Similarity	NPD7057	Phase 3
0.7429	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD8127	Discontinued
0.7361	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD6685	Approved
0.7214	Intermediate Similarity	NPD7741	Discontinued
0.7211	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8166	Discontinued
0.7192	Intermediate Similarity	NPD5736	Approved
0.7174	Intermediate Similarity	NPD2629	Approved
0.711	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7305	Phase 1
0.7097	Intermediate Similarity	NPD4628	Phase 3
0.7089	Intermediate Similarity	NPD6273	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.7076	Intermediate Similarity	NPD8368	Discontinued
0.7052	Intermediate Similarity	NPD8407	Phase 2
0.7021	Intermediate Similarity	NPD7610	Discontinued
0.702	Intermediate Similarity	NPD5735	Approved
0.7	Intermediate Similarity	NPD4198	Discontinued
0.6994	Remote Similarity	NPD5761	Phase 2
0.6994	Remote Similarity	NPD5760	Phase 2
0.6992	Remote Similarity	NPD6647	Phase 2
0.6992	Remote Similarity	NPD5765	Approved
0.6977	Remote Similarity	NPD7685	Pre-registration
0.6977	Remote Similarity	NPD6765	Approved
0.6977	Remote Similarity	NPD6764	Approved
0.6972	Remote Similarity	NPD6319	Approved
0.6971	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8434	Phase 2
0.6957	Remote Similarity	NPD8297	Approved
0.6957	Remote Similarity	NPD6912	Phase 3
0.6943	Remote Similarity	NPD6190	Approved
0.6939	Remote Similarity	NPD7319	Approved
0.6913	Remote Similarity	NPD7055	Discontinued
0.6906	Remote Similarity	NPD4632	Approved
0.6903	Remote Similarity	NPD5762	Approved
0.6903	Remote Similarity	NPD5763	Approved
0.6893	Remote Similarity	NPD8360	Approved
0.6893	Remote Similarity	NPD8435	Approved
0.6893	Remote Similarity	NPD8361	Approved
0.6892	Remote Similarity	NPD6085	Phase 2
0.6892	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7736	Approved
0.6866	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6010	Discontinued
0.6842	Remote Similarity	NPD4140	Approved
0.6835	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3094	Phase 2
0.6818	Remote Similarity	NPD6784	Approved
0.6818	Remote Similarity	NPD7638	Approved
0.6818	Remote Similarity	NPD6785	Approved
0.6812	Remote Similarity	NPD2067	Discontinued
0.6811	Remote Similarity	NPD7497	Discontinued
0.6803	Remote Similarity	NPD7078	Approved
0.6802	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3092	Approved
0.6781	Remote Similarity	NPD7492	Approved
0.6776	Remote Similarity	NPD8032	Phase 2
0.6767	Remote Similarity	NPD7640	Approved
0.6767	Remote Similarity	NPD7639	Approved
0.6765	Remote Similarity	NPD5048	Discontinued
0.6763	Remote Similarity	NPD6649	Approved
0.6763	Remote Similarity	NPD6650	Approved
0.6763	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7115	Discovery
0.6759	Remote Similarity	NPD5126	Approved
0.6759	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5125	Phase 3
0.6755	Remote Similarity	NPD7008	Discontinued
0.6746	Remote Similarity	NPD7199	Phase 2
0.6736	Remote Similarity	NPD7009	Phase 2
0.6736	Remote Similarity	NPD6054	Approved
0.6735	Remote Similarity	NPD6616	Approved
0.6733	Remote Similarity	NPD7084	Phase 3
0.6708	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7028	Phase 2
0.6707	Remote Similarity	NPD4965	Approved
0.6707	Remote Similarity	NPD4967	Phase 2
0.6707	Remote Similarity	NPD4966	Approved
0.6691	Remote Similarity	NPD5909	Discontinued
0.669	Remote Similarity	NPD5951	Approved
0.669	Remote Similarity	NPD8033	Approved
0.6688	Remote Similarity	NPD6002	Phase 3
0.6688	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6005	Phase 3
0.6688	Remote Similarity	NPD6004	Phase 3
0.6685	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD8485	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6646	Remote Similarity	NPD7458	Discontinued
0.6644	Remote Similarity	NPD3019	Approved
0.6644	Remote Similarity	NPD6370	Approved
0.6643	Remote Similarity	NPD8130	Phase 1
0.6643	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6009	Approved
0.6642	Remote Similarity	NPD6008	Approved
0.6642	Remote Similarity	NPD2066	Phase 3
0.6642	Remote Similarity	NPD7798	Approved
0.6627	Remote Similarity	NPD37	Approved
0.6627	Remote Similarity	NPD6234	Discontinued
0.6621	Remote Similarity	NPD8377	Approved
0.6621	Remote Similarity	NPD8294	Approved
0.6619	Remote Similarity	NPD6373	Approved
0.6619	Remote Similarity	NPD6372	Approved
0.6605	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3764	Approved
0.6599	Remote Similarity	NPD7604	Phase 2
0.6597	Remote Similarity	NPD7327	Approved
0.6597	Remote Similarity	NPD7328	Approved
0.6596	Remote Similarity	NPD6053	Discontinued
0.6596	Remote Similarity	NPD6882	Approved
0.6594	Remote Similarity	NPD5697	Approved
0.6587	Remote Similarity	NPD7819	Suspended
0.6582	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6355	Discontinued
0.6577	Remote Similarity	NPD8293	Discontinued
0.6575	Remote Similarity	NPD8379	Approved
0.6575	Remote Similarity	NPD6016	Approved
0.6575	Remote Similarity	NPD8378	Approved
0.6575	Remote Similarity	NPD8296	Approved
0.6575	Remote Similarity	NPD5983	Phase 2
0.6575	Remote Similarity	NPD6015	Approved
0.6575	Remote Similarity	NPD8380	Approved
0.6575	Remote Similarity	NPD8335	Approved
0.6575	Remote Similarity	NPD7503	Approved
0.6571	Remote Similarity	NPD7290	Approved
0.6571	Remote Similarity	NPD7102	Approved
0.6571	Remote Similarity	NPD6883	Approved
0.657	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5647	Approved
0.6554	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7228	Approved
0.6552	Remote Similarity	NPD7516	Approved
0.6547	Remote Similarity	NPD6011	Approved
0.6547	Remote Similarity	NPD6686	Approved
0.6545	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6653	Approved
0.6538	Remote Similarity	NPD6353	Approved
0.6531	Remote Similarity	NPD3095	Discontinued
0.6531	Remote Similarity	NPD2932	Approved
0.6531	Remote Similarity	NPD5988	Approved
0.6529	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD6847	Approved
0.6522	Remote Similarity	NPD6675	Approved
0.6522	Remote Similarity	NPD6402	Approved
0.6522	Remote Similarity	NPD5739	Approved
0.6522	Remote Similarity	NPD7128	Approved
0.6519	Remote Similarity	NPD7137	Phase 2
0.6517	Remote Similarity	NPD8312	Approved
0.6517	Remote Similarity	NPD8313	Approved
0.6515	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6336	Discontinued
0.651	Remote Similarity	NPD6637	Approved
0.6507	Remote Similarity	NPD6059	Approved
0.6507	Remote Similarity	NPD3091	Approved
0.65	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6014	Approved
0.65	Remote Similarity	NPD2182	Approved
0.65	Remote Similarity	NPD6013	Approved
0.65	Remote Similarity	NPD6012	Approved
0.65	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1929	Approved
0.6496	Remote Similarity	NPD1930	Approved
0.6494	Remote Similarity	NPD7473	Discontinued
0.6488	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3026	Approved
0.6486	Remote Similarity	NPD3023	Approved
0.6478	Remote Similarity	NPD7266	Discontinued
0.6471	Remote Similarity	NPD7075	Discontinued
0.6463	Remote Similarity	NPD3025	Approved
0.6463	Remote Similarity	NPD3024	Approved
0.6461	Remote Similarity	NPD7962	Phase 2
0.646	Remote Similarity	NPD4110	Phase 3
0.646	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4766	Approved
0.6454	Remote Similarity	NPD4634	Approved
0.6446	Remote Similarity	NPD3226	Approved
0.6429	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5844	Phase 1

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