NPASS Compound

Structure

NPC474935 OpenBabel07101718232D 53 58 0 0 1 0 0 0 0 0999 V2000 -2.2373 0.6912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5751 2.0503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1594 -4.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6331 0.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4420 1.0367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4123 0.7948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3367 -1.3520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0368 -5.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0599 -4.1839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1708 -6.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0368 -4.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0986 -4.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3018 -3.2136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3047 -5.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1708 -4.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3793 -3.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5824 -2.5189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2933 -3.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2727 0.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9025 -1.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3279 0.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3862 2.3259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0254 -4.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0715 -0.2624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3047 -4.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6212 -2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8636 0.6610 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5727 -2.9972 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1594 -2.9972 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3158 -0.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5147 -1.0217 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2933 -1.4972 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2212 -1.6809 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5012 -0.5191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4387 -4.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9018 -2.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7176 0.0754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5727 -1.9972 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1594 -1.9972 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6281 3.2962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8914 -4.9972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0690 -0.3322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5727 -4.9972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1438 -1.1296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7471 -2.8062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9817 -0.1903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4958 -0.4145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1055 1.6313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0254 -3.4972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5123 -1.0915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4387 -3.4972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9406 -2.3755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 37 1 0 0 0 0 6 37 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 14 25 2 0 0 0 0 15 25 1 0 0 0 0 16 26 2 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 27 1 0 0 0 0 19 40 1 0 0 0 0 20 39 1 0 0 0 0 20 48 1 0 0 0 0 21 27 1 0 0 0 0 21 30 2 0 0 0 0 22 41 2 0 0 0 0 22 49 1 0 0 0 0 23 42 2 0 0 0 0 23 50 1 0 0 0 0 24 43 2 0 0 0 0 24 51 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 49 1 1 0 0 0 28 38 1 6 0 0 0 28 52 1 0 0 0 0 29 39 1 1 0 0 0 29 50 1 0 0 0 0 30 31 1 0 0 0 0 30 37 1 0 0 0 0 31 33 1 0 0 0 0 31 51 1 6 0 0 0 32 34 1 0 0 0 0 32 38 1 6 0 0 0 32 39 1 0 0 0 0 33 38 1 1 0 0 0 33 53 1 0 0 0 0 34 40 1 1 0 0 0 34 48 1 0 0 0 0 35 44 2 0 0 0 0 35 52 1 0 0 0 0 36 45 2 0 0 0 0 36 53 1 0 0 0 0 37 40 1 0 0 0 0 38 7 1 6 0 0 0 39 46 1 1 0 0 0 40 47 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	734.29
Volume:	731.693
LogP:	4.551
LogD:	2.392
LogS:	-4.468
# Rotatable Bonds:	12
TPSA:	181.19
# H-Bond Aceptor:	13
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	5.825
Fsp3:	0.525
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:	-5.341
MDCK Permeability:	9.155987936537713e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.918
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241
Plasma Protein Binding (PPB):	85.17253875732422%
Volume Distribution (VD):	2.379
Pgp-substrate:	7.800715446472168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.478
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.119
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.368
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	4.686
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.272
Human Hepatotoxicity (H-HT):	0.477
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.214
Maximum Recommended Daily Dose:	0.305
Skin Sensitization:	0.114
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC474935

Natural Product ID:	NPC474935
*Common Name:**	XHAFKIWZKZKHOE-JFNIHIAOSA-N
IUPAC Name:	n.a.
Synonyms:	7,9-Dibenzoyltaxumairol P
Standard InCHIKey:	XHAFKIWZKZKHOE-JFNIHIAOSA-N
Standard InCHI:	InChI=1S/C40H46O13/c1-21-27(49-22(2)41)19-40(47)34-32-38(7,33(53-36(45)26-16-12-9-13-17-26)31(51-24(4)43)30(21)37(40,5)6)28(52-35(44)25-14-10-8-11-15-25)18-29(50-23(3)42)39(32,46)20-48-34/h8-17,27-29,31-34,46-47H,18-20H2,1-7H3/t27-,28-,29-,31+,32-,33-,34-,38+,39-,40+/m0/s1
SMILES:	CC(=O)O[C@@H]1C2=C(C)[C@@H](OC(=O)C)C[C@@](C2(C)C)(O)[C@@H]2[C@H]3[C@@]([C@H]1OC(=O)c1ccccc1)(C)[C@@H](OC(=O)c1ccccc1)C[C@@H]([C@@]3(O)CO2)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488534
PubChem CID:	10865491
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids 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
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1016/j.tet.2004.10.110]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[12502326]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	twig	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15679325]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220355]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11554	Taxus sumatrana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11554	Taxus sumatrana	Species	Taxaceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	12.8	ug.mL-1	PMID[558448]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.02	ug.mL-1	PMID[558448]

☑ 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 NPC474935 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	1078
0.2-0.3	2335
0.3-0.4	4453
0.4-0.5	9146
0.5-0.6	11937
0.6-0.7	11540
0.7-0.8	1496
0.8-0.85	221
0.85-0.9	81
0.9-0.95	118
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.971	High Similarity	NPC95810
0.971	High Similarity	NPC125106
0.971	High Similarity	NPC163719
0.971	High Similarity	NPC472573
0.971	High Similarity	NPC476974
0.971	High Similarity	NPC57628
0.971	High Similarity	NPC25768
0.971	High Similarity	NPC472569
0.971	High Similarity	NPC11685
0.971	High Similarity	NPC95265
0.971	High Similarity	NPC472570
0.971	High Similarity	NPC188865
0.971	High Similarity	NPC70716
0.964	High Similarity	NPC471104
0.964	High Similarity	NPC200471
0.964	High Similarity	NPC184817
0.964	High Similarity	NPC469349
0.964	High Similarity	NPC70403
0.964	High Similarity	NPC472572
0.964	High Similarity	NPC470159
0.964	High Similarity	NPC472568
0.964	High Similarity	NPC472571
0.964	High Similarity	NPC174982
0.964	High Similarity	NPC96903
0.964	High Similarity	NPC473088
0.964	High Similarity	NPC472575
0.964	High Similarity	NPC29704
0.964	High Similarity	NPC476973
0.964	High Similarity	NPC177940
0.964	High Similarity	NPC470157
0.964	High Similarity	NPC171525
0.964	High Similarity	NPC158663
0.9635	High Similarity	NPC16912
0.9568	High Similarity	NPC475759
0.9568	High Similarity	NPC241951
0.9568	High Similarity	NPC475122
0.9568	High Similarity	NPC470152
0.9565	High Similarity	NPC34012
0.9562	High Similarity	NPC97667
0.9562	High Similarity	NPC171207
0.9504	High Similarity	NPC281717
0.9496	High Similarity	NPC163087
0.9493	High Similarity	NPC472576
0.9493	High Similarity	NPC41481
0.9493	High Similarity	NPC97947
0.9493	High Similarity	NPC118080
0.9493	High Similarity	NPC87448
0.9493	High Similarity	NPC27377
0.9493	High Similarity	NPC291599
0.9493	High Similarity	NPC224491
0.9437	High Similarity	NPC476975
0.9437	High Similarity	NPC270590
0.9437	High Similarity	NPC266265
0.9437	High Similarity	NPC471101
0.9437	High Similarity	NPC301556
0.9437	High Similarity	NPC92293
0.942	High Similarity	NPC48017
0.942	High Similarity	NPC4341
0.942	High Similarity	NPC184747
0.942	High Similarity	NPC211137
0.942	High Similarity	NPC473613
0.942	High Similarity	NPC473060
0.942	High Similarity	NPC473081
0.942	High Similarity	NPC473109
0.942	High Similarity	NPC200592
0.942	High Similarity	NPC473758
0.942	High Similarity	NPC147880
0.942	High Similarity	NPC473112
0.942	High Similarity	NPC43241
0.942	High Similarity	NPC275592
0.942	High Similarity	NPC90614
0.942	High Similarity	NPC476094
0.942	High Similarity	NPC100913
0.942	High Similarity	NPC473085
0.9371	High Similarity	NPC473214
0.9371	High Similarity	NPC470245
0.9362	High Similarity	NPC472556
0.9348	High Similarity	NPC210591
0.9348	High Similarity	NPC475652
0.9348	High Similarity	NPC214550
0.9306	High Similarity	NPC470153
0.9301	High Similarity	NPC473215
0.9291	High Similarity	NPC38696
0.9281	High Similarity	NPC472547
0.9275	High Similarity	NPC283375
0.9275	High Similarity	NPC183122
0.927	High Similarity	NPC66761
0.927	High Similarity	NPC17877
0.927	High Similarity	NPC472577
0.927	High Similarity	NPC195647
0.927	High Similarity	NPC291638
0.9252	High Similarity	NPC472393
0.9241	High Similarity	NPC472548
0.922	High Similarity	NPC191082
0.922	High Similarity	NPC246480
0.922	High Similarity	NPC177340
0.922	High Similarity	NPC270498
0.922	High Similarity	NPC147217
0.922	High Similarity	NPC139067
0.922	High Similarity	NPC473673
0.922	High Similarity	NPC475429
0.9203	High Similarity	NPC472551
0.9203	High Similarity	NPC472545
0.9197	High Similarity	NPC474608
0.9184	High Similarity	NPC217091
0.9155	High Similarity	NPC470231
0.9155	High Similarity	NPC51314
0.9155	High Similarity	NPC67777
0.9149	High Similarity	NPC472546
0.9137	High Similarity	NPC39549
0.9116	High Similarity	NPC282239
0.9116	High Similarity	NPC472549
0.911	High Similarity	NPC477905
0.9097	High Similarity	NPC217918
0.9065	High Similarity	NPC472372
0.9065	High Similarity	NPC472374
0.9054	High Similarity	NPC106895
0.9041	High Similarity	NPC51602
0.9028	High Similarity	NPC473602
0.9028	High Similarity	NPC209592
0.9028	High Similarity	NPC48599
0.9007	High Similarity	NPC477904
0.9007	High Similarity	NPC183270
0.8986	High Similarity	NPC473670
0.8986	High Similarity	NPC34066
0.8986	High Similarity	NPC21410
0.8973	High Similarity	NPC91730
0.8973	High Similarity	NPC469448
0.8973	High Similarity	NPC31829
0.8966	High Similarity	NPC473760
0.8951	High Similarity	NPC91703
0.8944	High Similarity	NPC266374
0.8933	High Similarity	NPC471102
0.8912	High Similarity	NPC471103
0.8912	High Similarity	NPC197037
0.8905	High Similarity	NPC147561
0.8897	High Similarity	NPC240115
0.8889	High Similarity	NPC34943
0.8873	High Similarity	NPC475400
0.8859	High Similarity	NPC26033
0.8859	High Similarity	NPC228204
0.8859	High Similarity	NPC473611
0.8859	High Similarity	NPC469422
0.8844	High Similarity	NPC254558
0.8844	High Similarity	NPC7095
0.8844	High Similarity	NPC112216
0.8828	High Similarity	NPC127857
0.8819	High Similarity	NPC477894
0.8808	High Similarity	NPC469399
0.8803	High Similarity	NPC472395
0.8803	High Similarity	NPC472371
0.88	High Similarity	NPC326235
0.88	High Similarity	NPC323001
0.8792	High Similarity	NPC472030
0.8792	High Similarity	NPC158333
0.8792	High Similarity	NPC473414
0.8792	High Similarity	NPC304876
0.8792	High Similarity	NPC265395
0.8792	High Similarity	NPC472005
0.8792	High Similarity	NPC134685
0.8792	High Similarity	NPC248265
0.8792	High Similarity	NPC237549
0.8792	High Similarity	NPC11588
0.8792	High Similarity	NPC472022
0.8792	High Similarity	NPC77719
0.8792	High Similarity	NPC229545
0.8792	High Similarity	NPC1173
0.8792	High Similarity	NPC219419
0.8792	High Similarity	NPC257213
0.8792	High Similarity	NPC242262
0.8792	High Similarity	NPC249471
0.8792	High Similarity	NPC256142
0.8784	High Similarity	NPC101043
0.8784	High Similarity	NPC306799
0.8777	High Similarity	NPC472394
0.8776	High Similarity	NPC60509
0.8776	High Similarity	NPC250046
0.8776	High Similarity	NPC76103
0.8776	High Similarity	NPC81698
0.8767	High Similarity	NPC20255
0.875	High Similarity	NPC477623
0.875	High Similarity	NPC192658
0.8742	High Similarity	NPC318447
0.8742	High Similarity	NPC322048
0.8733	High Similarity	NPC112523
0.8733	High Similarity	NPC469730
0.8733	High Similarity	NPC473632
0.8733	High Similarity	NPC132599
0.8733	High Similarity	NPC114410
0.8733	High Similarity	NPC259144
0.8733	High Similarity	NPC114357
0.8733	High Similarity	NPC155329
0.8716	High Similarity	NPC165260
0.8716	High Similarity	NPC161239
0.8716	High Similarity	NPC198455
0.8699	High Similarity	NPC125882
0.8699	High Similarity	NPC92867
0.8699	High Similarity	NPC471107
0.8699	High Similarity	NPC471100
0.8699	High Similarity	NPC311825

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 NPC474935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	707
0.2-0.3	1413
0.3-0.4	2755
0.4-0.5	2380
0.5-0.6	1248
0.6-0.7	372
0.7-0.8	29
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
0.821	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7236	Approved
0.8036	Intermediate Similarity	NPD8434	Phase 2
0.8024	Intermediate Similarity	NPD8407	Phase 2
0.7986	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD8368	Discontinued
0.7941	Intermediate Similarity	NPD8361	Approved
0.7941	Intermediate Similarity	NPD8435	Approved
0.7941	Intermediate Similarity	NPD8360	Approved
0.7935	Intermediate Similarity	NPD7239	Suspended
0.7927	Intermediate Similarity	NPD7799	Discontinued
0.7824	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8485	Approved
0.7558	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7008	Discontinued
0.7485	Intermediate Similarity	NPD7058	Phase 2
0.7485	Intermediate Similarity	NPD7057	Phase 3
0.7484	Intermediate Similarity	NPD8166	Discontinued
0.7414	Intermediate Similarity	NPD8150	Discontinued
0.741	Intermediate Similarity	NPD8127	Discontinued
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD3764	Approved
0.7305	Intermediate Similarity	NPD4198	Discontinued
0.7297	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7961	Discontinued
0.7273	Intermediate Similarity	NPD7741	Discontinued
0.7251	Intermediate Similarity	NPD5844	Phase 1
0.725	Intermediate Similarity	NPD6273	Approved
0.7237	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2629	Approved
0.7234	Intermediate Similarity	NPD5951	Approved
0.7215	Intermediate Similarity	NPD6190	Approved
0.7195	Intermediate Similarity	NPD37	Approved
0.7194	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6234	Discontinued
0.7179	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5126	Approved
0.7172	Intermediate Similarity	NPD5125	Phase 3
0.7169	Intermediate Similarity	NPD4965	Approved
0.7169	Intermediate Similarity	NPD4967	Phase 2
0.7169	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4966	Approved
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7105	Intermediate Similarity	NPD8462	Phase 1
0.7093	Intermediate Similarity	NPD7228	Approved
0.7055	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8313	Approved
0.7045	Intermediate Similarity	NPD8312	Approved
0.7044	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7003	Approved
0.7035	Intermediate Similarity	NPD7473	Discontinued
0.7024	Intermediate Similarity	NPD7075	Discontinued
0.6975	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6858	Approved
0.6972	Remote Similarity	NPD7094	Approved
0.697	Remote Similarity	NPD6599	Discontinued
0.697	Remote Similarity	NPD4380	Phase 2
0.6964	Remote Similarity	NPD7768	Phase 2
0.6959	Remote Similarity	NPD8404	Phase 2
0.6959	Remote Similarity	NPD6232	Discontinued
0.6952	Remote Similarity	NPD7497	Discontinued
0.6946	Remote Similarity	NPD8455	Phase 2
0.6941	Remote Similarity	NPD5494	Approved
0.6937	Remote Similarity	NPD3750	Approved
0.6932	Remote Similarity	NPD7240	Approved
0.6932	Remote Similarity	NPD7685	Pre-registration
0.6929	Remote Similarity	NPD2182	Approved
0.6909	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5402	Approved
0.6905	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6355	Discontinued
0.6855	Remote Similarity	NPD7266	Discontinued
0.6849	Remote Similarity	NPD7610	Discontinued
0.6846	Remote Similarity	NPD6287	Discontinued
0.6845	Remote Similarity	NPD5760	Phase 2
0.6845	Remote Similarity	NPD5761	Phase 2
0.6839	Remote Similarity	NPD6663	Approved
0.6836	Remote Similarity	NPD6764	Approved
0.6836	Remote Similarity	NPD6765	Approved
0.6836	Remote Similarity	NPD6559	Discontinued
0.6835	Remote Similarity	NPD3748	Approved
0.6831	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7411	Suspended
0.681	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3226	Approved
0.6805	Remote Similarity	NPD3817	Phase 2
0.6802	Remote Similarity	NPD7199	Phase 2
0.6797	Remote Similarity	NPD5736	Approved
0.6792	Remote Similarity	NPD5404	Approved
0.6792	Remote Similarity	NPD2935	Discontinued
0.6792	Remote Similarity	NPD5406	Approved
0.6792	Remote Similarity	NPD5408	Approved
0.6792	Remote Similarity	NPD5405	Approved
0.6788	Remote Similarity	NPD5403	Approved
0.6786	Remote Similarity	NPD6801	Discontinued
0.678	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7699	Phase 2
0.6774	Remote Similarity	NPD7700	Phase 2
0.6768	Remote Similarity	NPD5401	Approved
0.6768	Remote Similarity	NPD2533	Approved
0.6768	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2532	Approved
0.6768	Remote Similarity	NPD2534	Approved
0.6759	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD230	Phase 1
0.675	Remote Similarity	NPD2346	Discontinued
0.675	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD8319	Approved
0.6737	Remote Similarity	NPD8320	Phase 1
0.6731	Remote Similarity	NPD6233	Phase 2
0.6731	Remote Similarity	NPD7715	Approved
0.6731	Remote Similarity	NPD7714	Approved
0.6731	Remote Similarity	NPD7713	Phase 3
0.6725	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1238	Approved
0.671	Remote Similarity	NPD7095	Approved
0.6707	Remote Similarity	NPD6799	Approved
0.6705	Remote Similarity	NPD3818	Discontinued
0.6703	Remote Similarity	NPD6534	Approved
0.6703	Remote Similarity	NPD6535	Approved
0.6691	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1930	Approved
0.6691	Remote Similarity	NPD1929	Approved
0.6687	Remote Similarity	NPD2438	Suspended
0.6686	Remote Similarity	NPD1934	Approved
0.6686	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6166	Phase 2
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6784	Approved
0.6685	Remote Similarity	NPD6785	Approved
0.6684	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1465	Phase 2
0.6643	Remote Similarity	NPD164	Approved
0.6629	Remote Similarity	NPD7074	Phase 3
0.6628	Remote Similarity	NPD3749	Approved
0.6627	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4110	Phase 3
0.6625	Remote Similarity	NPD7305	Phase 1
0.6625	Remote Similarity	NPD2799	Discontinued
0.6624	Remote Similarity	NPD8032	Phase 2
0.661	Remote Similarity	NPD3751	Discontinued
0.6609	Remote Similarity	NPD6959	Discontinued
0.6594	Remote Similarity	NPD7798	Approved
0.6577	Remote Similarity	NPD9545	Approved
0.6575	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7054	Approved
0.6573	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7229	Phase 3
0.657	Remote Similarity	NPD3882	Suspended
0.6564	Remote Similarity	NPD7874	Approved
0.6564	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2313	Discontinued
0.6552	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2801	Approved
0.6545	Remote Similarity	NPD6823	Phase 2
0.6543	Remote Similarity	NPD6005	Phase 3
0.6543	Remote Similarity	NPD6004	Phase 3
0.6543	Remote Similarity	NPD6002	Phase 3
0.6543	Remote Similarity	NPD5763	Approved
0.6543	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5762	Approved
0.6538	Remote Similarity	NPD6832	Phase 2
0.6536	Remote Similarity	NPD7472	Approved
0.6528	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2067	Discontinued
0.6526	Remote Similarity	NPD6782	Approved
0.6526	Remote Similarity	NPD6780	Approved
0.6526	Remote Similarity	NPD6778	Approved
0.6526	Remote Similarity	NPD6779	Approved
0.6526	Remote Similarity	NPD6776	Approved
0.6526	Remote Similarity	NPD6781	Approved
0.6526	Remote Similarity	NPD6777	Approved
0.6525	Remote Similarity	NPD5909	Discontinued
0.6522	Remote Similarity	NPD4308	Phase 3
0.6519	Remote Similarity	NPD4338	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