NPASS Compound

Structure

NPC209592 OpenBabel07101719162D 56 61 0 0 1 0 0 0 0 0999 V2000 -3.6262 -3.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 2.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4289 -0.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7913 -1.6392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1835 -2.5552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9949 -0.3154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7979 -0.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2570 -0.8724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2702 -3.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0473 -2.7575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4702 -2.8861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1978 -4.3971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4436 -3.5146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6935 -1.8562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5978 -3.3062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3255 -4.8172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4861 -3.3702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7361 -1.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8385 1.4524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1232 -3.0920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9683 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6855 -2.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5156 2.4206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2134 0.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -1.3538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4341 -1.6199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5255 -4.2718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1324 -2.4689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9469 -3.6010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6771 0.9683 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9683 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3183 -2.0790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8638 -1.2790 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8385 -0.4841 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5784 -0.3537 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6942 -1.4416 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2193 -5.1120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1750 -2.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9279 -1.2813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3528 -2.1513 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 -3.3541 2.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9232 0.6780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6506 -0.4098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3693 -1.3693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2916 -6.0775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5713 -3.0816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0380 -1.2143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9683 0.9683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5156 1.4524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2882 0.3048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1563 -2.0124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0193 -4.5665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8212 -1.4233 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2506 -0.9353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 39 1 0 0 0 0 7 39 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 27 2 0 0 0 0 16 27 1 0 0 0 0 17 28 2 0 0 0 0 18 28 1 0 0 0 0 19 30 1 0 0 0 0 19 31 1 0 0 0 0 20 29 1 0 0 0 0 20 41 1 0 0 0 0 21 42 1 0 0 0 0 21 50 1 0 0 0 0 22 29 1 0 0 0 0 22 32 2 0 0 0 0 23 43 2 0 0 0 0 23 51 1 0 0 0 0 24 44 2 0 0 0 0 24 52 1 0 0 0 0 25 45 2 0 0 0 0 25 53 1 0 0 0 0 26 46 2 0 0 0 0 26 56 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 29 54 1 6 0 0 0 30 40 1 1 0 0 0 30 51 1 0 0 0 0 31 42 1 1 0 0 0 31 50 1 0 0 0 0 32 33 1 0 0 0 0 32 41 1 0 0 0 0 33 35 1 0 0 0 0 33 55 1 1 0 0 0 34 36 1 0 0 0 0 34 40 1 1 0 0 0 34 42 1 0 0 0 0 35 40 1 6 0 0 0 35 52 1 0 0 0 0 36 41 1 6 0 0 0 36 53 1 0 0 0 0 37 47 2 0 0 0 0 37 54 1 0 0 0 0 38 48 2 0 0 0 0 38 55 1 0 0 0 0 39 49 1 0 0 0 0 40 8 1 1 0 0 0 41 39 1 1 0 0 0 42 56 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.35
Volume:	508.672
LogP:	4.772
LogD:	3.896
LogS:	-4.559
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.528
Synthetic Accessibility Score:	5.303
Fsp3:	0.966
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.752
MDCK Permeability:	2.1702353478758596e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.256
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.726
30% Bioavailability (F30%):	0.751

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.191
Plasma Protein Binding (PPB):	83.94645690917969%
Volume Distribution (VD):	1.616
Pgp-substrate:	16.636857986450195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.415
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	10.49
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.693
Human Hepatotoxicity (H-HT):	0.306
Drug-inuced Liver Injury (DILI):	0.555
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.876
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.717
Carcinogencity:	0.288
Eye Corrosion:	0.415
Eye Irritation:	0.024
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC209592

Natural Product ID:	NPC209592
*Common Name:**	HABDCYTZKFMLRY-QSXVJOPHSA-N
IUPAC Name:	n.a.
Synonyms:	10,13-Dibenzoyltaxacustin
Standard InCHIKey:	HABDCYTZKFMLRY-QSXVJOPHSA-N
Standard InCHI:	InChI=1S/C42H48O14/c1-22-29(54-37(47)27-15-11-9-12-16-27)20-41(39(6,7)49)32(22)33(55-38(48)28-17-13-10-14-18-28)35(52-24(3)44)40(8)30(51-23(2)43)19-31-42(21-50-31,56-26(5)46)34(40)36(41)53-25(4)45/h9-18,29-31,33-36,49H,19-21H2,1-8H3/t29-,30-,31+,33+,34-,35-,36-,40+,41-,42-/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H]2[C@@]3(CO[C@@H]3C[C@@H]([C@@]2(C)[C@H]([C@@H](C2=C([C@H](C[C@@]12C(O)(C)C)OC(=O)c1ccccc1)C)OC(=O)c1ccccc1)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447609
PubChem CID:	12038773
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
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	=	9.69	ug.mL-1	PMID[464269]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[464269]

☑ 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 NPC209592 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	309
0.1-0.2	1167
0.2-0.3	2426
0.3-0.4	5145
0.4-0.5	10452
0.5-0.6	11284
0.6-0.7	10629
0.7-0.8	956
0.8-0.85	160
0.85-0.9	153
0.9-0.95	8
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48599
0.9928	High Similarity	NPC473760
0.9786	High Similarity	NPC31829
0.964	High Similarity	NPC125882
0.9635	High Similarity	NPC266374
0.9571	High Similarity	NPC20255
0.95	High Similarity	NPC92867
0.95	High Similarity	NPC311825
0.9429	High Similarity	NPC34943
0.9301	High Similarity	NPC76103
0.9296	High Similarity	NPC240115
0.9286	High Similarity	NPC192658
0.9281	High Similarity	NPC162613
0.9281	High Similarity	NPC87934
0.9214	High Similarity	NPC16912
0.9209	High Similarity	NPC9905
0.9172	High Similarity	NPC96308
0.9155	High Similarity	NPC95810
0.9155	High Similarity	NPC472573
0.9155	High Similarity	NPC125106
0.9155	High Similarity	NPC163719
0.9155	High Similarity	NPC25768
0.9155	High Similarity	NPC188865
0.9155	High Similarity	NPC11685
0.9155	High Similarity	NPC476974
0.9155	High Similarity	NPC57628
0.9155	High Similarity	NPC472569
0.9155	High Similarity	NPC95265
0.9155	High Similarity	NPC70716
0.9155	High Similarity	NPC472570
0.9143	High Similarity	NPC97667
0.9143	High Similarity	NPC171207
0.9143	High Similarity	NPC90614
0.9116	High Similarity	NPC473611
0.9091	High Similarity	NPC476973
0.9091	High Similarity	NPC29704
0.9091	High Similarity	NPC171525
0.9091	High Similarity	NPC174982
0.9091	High Similarity	NPC96903
0.9091	High Similarity	NPC473088
0.9091	High Similarity	NPC184817
0.9091	High Similarity	NPC471104
0.9091	High Similarity	NPC177940
0.9091	High Similarity	NPC470159
0.9091	High Similarity	NPC472575
0.9091	High Similarity	NPC472572
0.9091	High Similarity	NPC472571
0.9091	High Similarity	NPC472568
0.9091	High Similarity	NPC158663
0.9091	High Similarity	NPC470157
0.9091	High Similarity	NPC200471
0.9091	High Similarity	NPC469349
0.9091	High Similarity	NPC70403
0.9085	High Similarity	NPC163087
0.9078	High Similarity	NPC87448
0.9078	High Similarity	NPC118080
0.9078	High Similarity	NPC291599
0.9078	High Similarity	NPC27377
0.9078	High Similarity	NPC41481
0.9078	High Similarity	NPC97947
0.9078	High Similarity	NPC472576
0.9028	High Similarity	NPC474935
0.9028	High Similarity	NPC473602
0.9021	High Similarity	NPC470152
0.9021	High Similarity	NPC475759
0.9021	High Similarity	NPC475122
0.9021	High Similarity	NPC241951
0.9007	High Similarity	NPC473085
0.9007	High Similarity	NPC100913
0.9007	High Similarity	NPC184747
0.9007	High Similarity	NPC4341
0.9007	High Similarity	NPC275592
0.9007	High Similarity	NPC473112
0.9007	High Similarity	NPC476094
0.9007	High Similarity	NPC48017
0.9007	High Similarity	NPC200592
0.9007	High Similarity	NPC473613
0.9007	High Similarity	NPC147880
0.9007	High Similarity	NPC473109
0.9007	High Similarity	NPC211137
0.9007	High Similarity	NPC473758
0.9007	High Similarity	NPC473060
0.9007	High Similarity	NPC473081
0.9007	High Similarity	NPC43241
0.8993	High Similarity	NPC66761
0.8993	High Similarity	NPC291638
0.8993	High Similarity	NPC17877
0.8993	High Similarity	NPC195647
0.8993	High Similarity	NPC472577
0.8986	High Similarity	NPC469730
0.8986	High Similarity	NPC132599
0.8986	High Similarity	NPC473632
0.8966	High Similarity	NPC327031
0.8966	High Similarity	NPC281717
0.8958	High Similarity	NPC472556
0.8951	High Similarity	NPC95449
0.8944	High Similarity	NPC224491
0.894	High Similarity	NPC476077
0.8936	High Similarity	NPC475652
0.8936	High Similarity	NPC210591
0.8936	High Similarity	NPC214550
0.8921	High Similarity	NPC474608
0.8904	High Similarity	NPC476975
0.8904	High Similarity	NPC266265
0.8904	High Similarity	NPC92293
0.8904	High Similarity	NPC270590
0.8904	High Similarity	NPC301556
0.8904	High Similarity	NPC471101
0.8897	High Similarity	NPC312393
0.8889	High Similarity	NPC38696
0.8881	High Similarity	NPC34012
0.8873	High Similarity	NPC472547
0.8865	High Similarity	NPC283375
0.8865	High Similarity	NPC183122
0.8844	High Similarity	NPC470245
0.8844	High Similarity	NPC473214
0.8819	High Similarity	NPC246480
0.8819	High Similarity	NPC191082
0.8819	High Similarity	NPC475429
0.8819	High Similarity	NPC139067
0.8819	High Similarity	NPC270498
0.8819	High Similarity	NPC473673
0.8819	High Similarity	NPC147217
0.8819	High Similarity	NPC177340
0.88	High Similarity	NPC326235
0.88	High Similarity	NPC323001
0.8794	High Similarity	NPC472545
0.8794	High Similarity	NPC472551
0.8784	High Similarity	NPC470153
0.8776	High Similarity	NPC473215
0.8767	High Similarity	NPC478263
0.8759	High Similarity	NPC51314
0.8759	High Similarity	NPC67777
0.8759	High Similarity	NPC470231
0.875	High Similarity	NPC472546
0.8742	High Similarity	NPC318447
0.8742	High Similarity	NPC322048
0.8732	High Similarity	NPC39549
0.8716	High Similarity	NPC476173
0.8707	High Similarity	NPC217918
0.8699	High Similarity	NPC478264
0.869	High Similarity	NPC477894
0.8667	High Similarity	NPC471135
0.8658	High Similarity	NPC51602
0.8633	High Similarity	NPC147561
0.8627	High Similarity	NPC326328
0.8627	High Similarity	NPC309991
0.8627	High Similarity	NPC323356
0.8627	High Similarity	NPC471138
0.8609	High Similarity	NPC34066
0.8609	High Similarity	NPC282239
0.86	High Similarity	NPC469648
0.86	High Similarity	NPC138641
0.86	High Similarity	NPC22571
0.86	High Similarity	NPC477905
0.86	High Similarity	NPC233581
0.86	High Similarity	NPC472548
0.86	High Similarity	NPC469647
0.86	High Similarity	NPC145649
0.86	High Similarity	NPC283875
0.8592	High Similarity	NPC477893
0.8591	High Similarity	NPC469448
0.8591	High Similarity	NPC91730
0.8581	High Similarity	NPC132652
0.8571	High Similarity	NPC127857
0.8562	High Similarity	NPC131966
0.8562	High Similarity	NPC191387
0.8562	High Similarity	NPC91703
0.8562	High Similarity	NPC319404
0.8553	High Similarity	NPC106895
0.8553	High Similarity	NPC475638
0.8553	High Similarity	NPC475548
0.8553	High Similarity	NPC290683
0.854	High Similarity	NPC284022
0.8533	High Similarity	NPC197037
0.8533	High Similarity	NPC471103
0.8531	High Similarity	NPC472374
0.8531	High Similarity	NPC472372
0.8526	High Similarity	NPC471134
0.8516	High Similarity	NPC55744
0.8497	Intermediate Similarity	NPC472393
0.8493	Intermediate Similarity	NPC182869
0.8487	Intermediate Similarity	NPC26033
0.8487	Intermediate Similarity	NPC469422
0.8487	Intermediate Similarity	NPC228204
0.8487	Intermediate Similarity	NPC472549
0.8483	Intermediate Similarity	NPC477904
0.8483	Intermediate Similarity	NPC183270
0.8472	Intermediate Similarity	NPC205305
0.8472	Intermediate Similarity	NPC327511
0.8472	Intermediate Similarity	NPC475373
0.8467	Intermediate Similarity	NPC254558
0.8467	Intermediate Similarity	NPC7095
0.8467	Intermediate Similarity	NPC112216
0.8462	Intermediate Similarity	NPC478125
0.8462	Intermediate Similarity	NPC477896
0.8446	Intermediate Similarity	NPC471107
0.8446	Intermediate Similarity	NPC471100
0.8442	Intermediate Similarity	NPC471102
0.8442	Intermediate Similarity	NPC469399

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 NPC209592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	755
0.2-0.3	1480
0.3-0.4	2788
0.4-0.5	2373
0.5-0.6	1181
0.6-0.7	300
0.7-0.8	18
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
0.7961	Intermediate Similarity	NPD7236	Approved
0.7821	Intermediate Similarity	NPD7239	Suspended
0.7771	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7799	Discontinued
0.7633	Intermediate Similarity	NPD8368	Discontinued
0.7616	Intermediate Similarity	NPD8434	Phase 2
0.7602	Intermediate Similarity	NPD8407	Phase 2
0.7529	Intermediate Similarity	NPD8435	Approved
0.7529	Intermediate Similarity	NPD8361	Approved
0.7529	Intermediate Similarity	NPD8360	Approved
0.7415	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7741	Discontinued
0.7378	Intermediate Similarity	NPD7058	Phase 2
0.7378	Intermediate Similarity	NPD7057	Phase 3
0.7356	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8127	Discontinued
0.7278	Intermediate Similarity	NPD8485	Approved
0.7267	Intermediate Similarity	NPD7008	Discontinued
0.725	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD3764	Approved
0.7171	Intermediate Similarity	NPD7961	Discontinued
0.7158	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7113	Intermediate Similarity	NPD2629	Approved
0.7113	Intermediate Similarity	NPD5951	Approved
0.7107	Intermediate Similarity	NPD6190	Approved
0.7071	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4198	Discontinued
0.7052	Intermediate Similarity	NPD5844	Phase 1
0.7044	Intermediate Similarity	NPD8166	Discontinued
0.7022	Intermediate Similarity	NPD8150	Discontinued
0.7013	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD37	Approved
0.6964	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4967	Phase 2
0.6964	Remote Similarity	NPD4966	Approved
0.6964	Remote Similarity	NPD4965	Approved
0.6962	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6663	Approved
0.6946	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7473	Discontinued
0.6932	Remote Similarity	NPD7685	Pre-registration
0.6929	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2182	Approved
0.6923	Remote Similarity	NPD7075	Discontinued
0.6909	Remote Similarity	NPD7458	Discontinued
0.6908	Remote Similarity	NPD5736	Approved
0.6892	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6234	Discontinued
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7768	Phase 2
0.6862	Remote Similarity	NPD7497	Discontinued
0.686	Remote Similarity	NPD6232	Discontinued
0.6853	Remote Similarity	NPD7094	Approved
0.6853	Remote Similarity	NPD6858	Approved
0.6845	Remote Similarity	NPD5760	Phase 2
0.6845	Remote Similarity	NPD5761	Phase 2
0.6832	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7003	Approved
0.6824	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5126	Approved
0.6824	Remote Similarity	NPD5125	Phase 3
0.6805	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2935	Discontinued
0.6788	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4380	Phase 2
0.6766	Remote Similarity	NPD6599	Discontinued
0.676	Remote Similarity	NPD8313	Approved
0.676	Remote Similarity	NPD8312	Approved
0.6758	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD8462	Phase 1
0.6752	Remote Similarity	NPD6355	Discontinued
0.6746	Remote Similarity	NPD8455	Phase 2
0.6744	Remote Similarity	NPD5494	Approved
0.6742	Remote Similarity	NPD6765	Approved
0.6742	Remote Similarity	NPD6764	Approved
0.6735	Remote Similarity	NPD7610	Discontinued
0.6733	Remote Similarity	NPD6287	Discontinued
0.673	Remote Similarity	NPD2799	Discontinued
0.6728	Remote Similarity	NPD3750	Approved
0.6726	Remote Similarity	NPD7411	Suspended
0.6715	Remote Similarity	NPD1238	Approved
0.6707	Remote Similarity	NPD3226	Approved
0.6707	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3817	Phase 2
0.6706	Remote Similarity	NPD5402	Approved
0.6705	Remote Similarity	NPD7228	Approved
0.6705	Remote Similarity	NPD7199	Phase 2
0.6691	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1930	Approved
0.6691	Remote Similarity	NPD1929	Approved
0.6687	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6801	Discontinued
0.6685	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6685	Approved
0.6647	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6005	Phase 3
0.6646	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD7266	Discontinued
0.6646	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6002	Phase 3
0.6646	Remote Similarity	NPD2346	Discontinued
0.6646	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD230	Phase 1
0.6644	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD164	Approved
0.6629	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3748	Approved
0.6624	Remote Similarity	NPD8032	Phase 2
0.6624	Remote Similarity	NPD6233	Phase 2
0.6616	Remote Similarity	NPD8404	Phase 2
0.6606	Remote Similarity	NPD6799	Approved
0.6603	Remote Similarity	NPD7095	Approved
0.6594	Remote Similarity	NPD7798	Approved
0.6593	Remote Similarity	NPD6785	Approved
0.6593	Remote Similarity	NPD6784	Approved
0.6591	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1934	Approved
0.6587	Remote Similarity	NPD5403	Approved
0.6584	Remote Similarity	NPD2438	Suspended
0.6584	Remote Similarity	NPD5408	Approved
0.6584	Remote Similarity	NPD5404	Approved
0.6584	Remote Similarity	NPD5406	Approved
0.6584	Remote Similarity	NPD5405	Approved
0.6582	Remote Similarity	NPD4140	Approved
0.6577	Remote Similarity	NPD9545	Approved
0.6571	Remote Similarity	NPD6647	Phase 2
0.6566	Remote Similarity	NPD2532	Approved
0.6566	Remote Similarity	NPD2534	Approved
0.6566	Remote Similarity	NPD5401	Approved
0.6566	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2533	Approved
0.6562	Remote Similarity	NPD7097	Phase 1
0.6561	Remote Similarity	NPD2313	Discontinued
0.6561	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6798	Discontinued
0.6556	Remote Similarity	NPD6559	Discontinued
0.6556	Remote Similarity	NPD7240	Approved
0.6543	Remote Similarity	NPD5763	Approved
0.6543	Remote Similarity	NPD5762	Approved
0.6538	Remote Similarity	NPD6832	Phase 2
0.6532	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2067	Discontinued
0.6525	Remote Similarity	NPD5909	Discontinued
0.6524	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4110	Phase 3
0.6519	Remote Similarity	NPD7713	Phase 3
0.6519	Remote Similarity	NPD7715	Approved
0.6519	Remote Similarity	NPD7714	Approved
0.6517	Remote Similarity	NPD3818	Discontinued
0.6516	Remote Similarity	NPD6085	Phase 2
0.6516	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7700	Phase 2
0.6508	Remote Similarity	NPD7699	Phase 2
0.6503	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6166	Phase 2
0.6494	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2796	Approved
0.648	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7229	Phase 3
0.6477	Remote Similarity	NPD8319	Approved
0.6477	Remote Similarity	NPD8320	Phase 1
0.6471	Remote Similarity	NPD7028	Phase 2
0.6471	Remote Similarity	NPD1608	Approved
0.6467	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD5765	Approved
0.6453	Remote Similarity	NPD2801	Approved
0.6453	Remote Similarity	NPD1465	Phase 2
0.6452	Remote Similarity	NPD2797	Approved
0.6444	Remote Similarity	NPD7074	Phase 3
0.6438	Remote Similarity	NPD6912	Phase 3
0.6437	Remote Similarity	NPD3749	Approved
0.6436	Remote Similarity	NPD6534	Approved
0.6436	Remote Similarity	NPD6535	Approved
0.6425	Remote Similarity	NPD7435	Discontinued
0.642	Remote Similarity	NPD1510	Phase 2
0.642	Remote Similarity	NPD6959	Discontinued
0.642	Remote Similarity	NPD4308	Phase 3
0.642	Remote Similarity	NPD7305	Phase 1
0.642	Remote Similarity	NPD7033	Discontinued
0.641	Remote Similarity	NPD2798	Approved
0.6408	Remote Similarity	NPD1237	Approved
0.6405	Remote Similarity	NPD4807	Approved
0.6405	Remote Similarity	NPD4806	Approved
0.6404	Remote Similarity	NPD7997	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