NPASS Compound

Structure

NPC57964 OpenBabel07101718322D 58 63 0 0 1 0 0 0 0 0999 V2000 -3.4100 4.9219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9675 -2.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1150 -2.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2736 -0.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3374 -0.1363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0497 -2.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0653 -2.3291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7050 0.9844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4521 -0.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7050 -0.9844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8882 3.6798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7144 2.1901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3673 0.9844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8525 -1.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4102 1.2539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0557 2.9216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7887 0.1880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5575 0.4922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5575 4.4297 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9675 -1.4766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2625 -2.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7887 1.7808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8525 1.4766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8525 1.4766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4100 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7050 -0.9844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7050 4.9219 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8200 -0.9844 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8525 4.4297 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8200 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8525 3.4453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9675 0.4922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8525 0.4922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4100 -0.9844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7050 2.9531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1150 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0689 0.5223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5575 -1.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7050 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8525 0.4922 0.0000 C 0 0 1 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 2.0929 2.7169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4100 -2.9531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7050 5.9062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6724 -1.4766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.9219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6724 0.4922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9675 1.4766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0318 0.7270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1567 3.0211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5575 3.4453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1150 -0.9844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2625 -1.4766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7050 1.9687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2625 0.4922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 23 1 0 0 0 0 4 39 1 0 0 0 0 5 39 1 0 0 0 0 6 40 1 0 0 0 0 7 40 1 0 0 0 0 9 42 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 18 1 0 0 0 0 14 28 1 0 0 0 0 15 39 1 0 0 0 0 16 44 1 0 0 0 0 17 42 1 0 0 0 0 18 43 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 20 41 1 0 0 0 0 21 1 1 6 0 0 0 21 29 1 0 0 0 0 21 54 1 0 0 0 0 22 2 1 6 0 0 0 22 30 1 0 0 0 0 22 55 1 0 0 0 0 23 45 2 0 0 0 0 23 56 1 0 0 0 0 24 25 1 0 0 0 0 24 44 1 1 0 0 0 25 42 1 6 0 0 0 26 35 1 0 0 0 0 26 57 1 6 0 0 0 27 36 1 0 0 0 0 27 58 1 6 0 0 0 28 40 1 0 0 0 0 28 41 1 1 0 0 0 29 31 1 0 0 0 0 29 46 1 6 0 0 0 30 32 1 0 0 0 0 30 47 1 6 0 0 0 31 33 1 0 0 0 0 31 48 1 6 0 0 0 32 34 1 0 0 0 0 32 49 1 6 0 0 0 33 37 1 0 0 0 0 33 50 1 1 0 0 0 34 38 1 0 0 0 0 34 51 1 1 0 0 0 35 41 1 1 0 0 0 35 43 1 0 0 0 0 36 40 1 0 0 0 0 36 56 1 6 0 0 0 37 54 1 0 0 0 0 37 57 1 6 0 0 0 38 55 1 0 0 0 0 38 58 1 6 0 0 0 39 52 1 0 0 0 0 41 8 1 1 0 0 0 42 43 1 1 0 0 0 43 10 1 1 0 0 0 44 11 1 1 0 0 0 44 53 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	828.52
Volume:	838.668
LogP:	3.964
LogD:	3.747
LogS:	-3.638
# Rotatable Bonds:	11
TPSA:	225.06
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.117
Synthetic Accessibility Score:	6.156
Fsp3:	0.977
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.278
MDCK Permeability:	0.00010140395170310512
Pgp-inhibitor:	0.994
Pgp-substrate:	0.26
Human Intestinal Absorption (HIA):	0.408
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.853

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	80.09253692626953%
Volume Distribution (VD):	0.442
Pgp-substrate:	8.039217948913574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.072
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	0.948
Half-life (T1/2):	0.509

ADMET: Toxicity

hERG Blockers:	0.434
Human Hepatotoxicity (H-HT):	0.126
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.344
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.46

Download Data

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

Natural Product: NPC57964

Natural Product ID:	NPC57964
*Common Name:**	Combretaside A
IUPAC Name:	[(2R,3S,5R,8R,9R,10S,11R,13R,14R,17S)-17-[(2R)-2,6-dihydroxy-6-methylheptan-2-yl]-4,4,8,10,14-pentamethyl-2,11-bis[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:
Standard InCHIKey:	LWECKXUQVPEFRN-WXVNMTHESA-N
Standard InCHI:	InChI=1S/C44H76O14/c1-21-29(46)31(48)33(50)37(54-21)57-26-19-25-24(44(11,53)16-12-15-39(4,5)52)13-17-42(25,9)43(10)18-14-28-40(6,7)36(56-23(3)45)27(20-41(28,8)35(26)43)58-38-34(51)32(49)30(47)22(2)55-38/h21-22,24-38,46-53H,12-20H2,1-11H3/t21-,22-,24+,25-,26-,27-,28+,29+,30+,31+,32+,33-,34-,35-,36-,37+,38+,41+,42-,43-,44-/m1/s1
SMILES:	CC(=O)O[C@@H]1[C@H](O[C@@H]2O[C@H](C)[C@@H]([C@@H]([C@H]2O)O)O)C[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2[C@H](O[C@@H]2O[C@H](C)[C@@H]([C@@H]([C@H]2O)O)O)C[C@H]2[C@@]1(C)CC[C@@H]2[C@@](CCCC(O)(C)C)(O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419357
PubChem CID:	73350745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO32465	combretum inflatum	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23978065]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>=	30.0	ug.mL-1	PMID[515946]

☑ 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 NPC57964 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	490
0.1-0.2	4226
0.2-0.3	11957
0.3-0.4	11466
0.4-0.5	5924
0.5-0.6	4103
0.6-0.7	2392
0.7-0.8	1588
0.8-0.85	261
0.85-0.9	228
0.9-0.95	56
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC94582
0.9667	High Similarity	NPC203434
0.9667	High Similarity	NPC238796
0.9667	High Similarity	NPC237071
0.9451	High Similarity	NPC296936
0.9444	High Similarity	NPC191915
0.9444	High Similarity	NPC151214
0.9432	High Similarity	NPC131466
0.9348	High Similarity	NPC470591
0.9255	High Similarity	NPC476838
0.9255	High Similarity	NPC476512
0.9255	High Similarity	NPC476839
0.9255	High Similarity	NPC472081
0.9255	High Similarity	NPC475574
0.9255	High Similarity	NPC108227
0.9239	High Similarity	NPC252056
0.9222	High Similarity	NPC210759
0.9222	High Similarity	NPC229801
0.9222	High Similarity	NPC307167
0.9205	High Similarity	NPC43912
0.9205	High Similarity	NPC140446
0.9158	High Similarity	NPC470029
0.9158	High Similarity	NPC134967
0.9158	High Similarity	NPC114700
0.9158	High Similarity	NPC310138
0.914	High Similarity	NPC210157
0.913	High Similarity	NPC92196
0.913	High Similarity	NPC477494
0.9111	High Similarity	NPC65550
0.9062	High Similarity	NPC97260
0.9062	High Similarity	NPC139181
0.9062	High Similarity	NPC476837
0.9022	High Similarity	NPC305418
0.9022	High Similarity	NPC45959
0.9022	High Similarity	NPC309866
0.9022	High Similarity	NPC252253
0.9011	High Similarity	NPC204881
0.9011	High Similarity	NPC293609
0.9011	High Similarity	NPC473830
0.9	High Similarity	NPC82955
0.9	High Similarity	NPC473472
0.8977	High Similarity	NPC290612
0.8947	High Similarity	NPC51579
0.8936	High Similarity	NPC477222
0.8936	High Similarity	NPC477223
0.8913	High Similarity	NPC172838
0.8913	High Similarity	NPC149400
0.8913	High Similarity	NPC137004
0.8913	High Similarity	NPC277774
0.8913	High Similarity	NPC144790
0.8913	High Similarity	NPC88962
0.8913	High Similarity	NPC473726
0.8901	High Similarity	NPC279329
0.8901	High Similarity	NPC223143
0.8889	High Similarity	NPC281004
0.8842	High Similarity	NPC209798
0.8842	High Similarity	NPC471375
0.8842	High Similarity	NPC471374
0.883	High Similarity	NPC476510
0.883	High Similarity	NPC139271
0.883	High Similarity	NPC304011
0.883	High Similarity	NPC121453
0.883	High Similarity	NPC142264
0.8817	High Similarity	NPC222731
0.8817	High Similarity	NPC473851
0.8817	High Similarity	NPC179859
0.8817	High Similarity	NPC477224
0.8817	High Similarity	NPC312678
0.8817	High Similarity	NPC294686
0.8817	High Similarity	NPC24960
0.8817	High Similarity	NPC131693
0.8817	High Similarity	NPC253268
0.8817	High Similarity	NPC174024
0.8817	High Similarity	NPC3538
0.8817	High Similarity	NPC473774
0.8817	High Similarity	NPC291547
0.8817	High Similarity	NPC475436
0.8817	High Similarity	NPC113500
0.8804	High Similarity	NPC36372
0.8804	High Similarity	NPC149966
0.8804	High Similarity	NPC5632
0.88	High Similarity	NPC43976
0.88	High Similarity	NPC51925
0.88	High Similarity	NPC125361
0.88	High Similarity	NPC296761
0.88	High Similarity	NPC154085
0.8791	High Similarity	NPC102725
0.8788	High Similarity	NPC203974
0.8776	High Similarity	NPC469827
0.875	High Similarity	NPC471428
0.875	High Similarity	NPC470030
0.875	High Similarity	NPC471426
0.875	High Similarity	NPC471427
0.8737	High Similarity	NPC470028
0.8737	High Similarity	NPC233649
0.8737	High Similarity	NPC472273
0.8723	High Similarity	NPC474399
0.871	High Similarity	NPC234352
0.871	High Similarity	NPC48339
0.871	High Similarity	NPC177834
0.871	High Similarity	NPC141769
0.871	High Similarity	NPC167644
0.871	High Similarity	NPC250393
0.871	High Similarity	NPC477451
0.871	High Similarity	NPC476669
0.871	High Similarity	NPC325828
0.871	High Similarity	NPC311246
0.871	High Similarity	NPC297348
0.871	High Similarity	NPC477547
0.871	High Similarity	NPC249204
0.87	High Similarity	NPC469826
0.87	High Similarity	NPC38217
0.87	High Similarity	NPC472988
0.8696	High Similarity	NPC473542
0.8667	High Similarity	NPC471410
0.8667	High Similarity	NPC471411
0.866	High Similarity	NPC477172
0.8646	High Similarity	NPC292775
0.8646	High Similarity	NPC473518
0.8632	High Similarity	NPC473287
0.8632	High Similarity	NPC473601
0.8632	High Similarity	NPC195297
0.8632	High Similarity	NPC156377
0.8627	High Similarity	NPC65167
0.8617	High Similarity	NPC291203
0.8617	High Similarity	NPC175
0.8617	High Similarity	NPC473503
0.8617	High Similarity	NPC264101
0.8617	High Similarity	NPC475325
0.8617	High Similarity	NPC471464
0.8617	High Similarity	NPC217205
0.8614	High Similarity	NPC236753
0.8614	High Similarity	NPC228190
0.8602	High Similarity	NPC476668
0.8602	High Similarity	NPC473637
0.86	High Similarity	NPC234160
0.8587	High Similarity	NPC20822
0.8557	High Similarity	NPC317019
0.8557	High Similarity	NPC20028
0.8544	High Similarity	NPC477489
0.8542	High Similarity	NPC83137
0.8542	High Similarity	NPC274200
0.8542	High Similarity	NPC232611
0.8542	High Similarity	NPC115165
0.8542	High Similarity	NPC475207
0.8542	High Similarity	NPC303069
0.8542	High Similarity	NPC476112
0.8542	High Similarity	NPC51520
0.8542	High Similarity	NPC307534
0.8542	High Similarity	NPC470861
0.8542	High Similarity	NPC470862
0.8526	High Similarity	NPC19400
0.8526	High Similarity	NPC211354
0.8526	High Similarity	NPC473727
0.8526	High Similarity	NPC107962
0.8526	High Similarity	NPC215570
0.8526	High Similarity	NPC473064
0.8526	High Similarity	NPC473067
0.8526	High Similarity	NPC473065
0.8526	High Similarity	NPC206003
0.8526	High Similarity	NPC6295
0.8526	High Similarity	NPC107188
0.8526	High Similarity	NPC473610
0.8526	High Similarity	NPC469710
0.8526	High Similarity	NPC475351
0.8515	High Similarity	NPC472079
0.8511	High Similarity	NPC182740
0.8511	High Similarity	NPC256104
0.8511	High Similarity	NPC122083
0.8511	High Similarity	NPC224003
0.8511	High Similarity	NPC171741
0.8511	High Similarity	NPC211845
0.8511	High Similarity	NPC470623
0.8511	High Similarity	NPC18724
0.8511	High Similarity	NPC323231
0.85	High Similarity	NPC473199
0.8462	Intermediate Similarity	NPC477283
0.8462	Intermediate Similarity	NPC155531
0.8462	Intermediate Similarity	NPC215968
0.8454	Intermediate Similarity	NPC157739
0.8454	Intermediate Similarity	NPC473638
0.8454	Intermediate Similarity	NPC473616
0.8454	Intermediate Similarity	NPC291548
0.8447	Intermediate Similarity	NPC469824
0.8438	Intermediate Similarity	NPC232037
0.8438	Intermediate Similarity	NPC128572
0.8438	Intermediate Similarity	NPC475625
0.8438	Intermediate Similarity	NPC470864
0.8438	Intermediate Similarity	NPC132080
0.8438	Intermediate Similarity	NPC470863
0.8438	Intermediate Similarity	NPC284104
0.8438	Intermediate Similarity	NPC160426
0.8438	Intermediate Similarity	NPC287483
0.8438	Intermediate Similarity	NPC470866
0.8438	Intermediate Similarity	NPC472989
0.8438	Intermediate Similarity	NPC98018
0.8438	Intermediate Similarity	NPC30856
0.8438	Intermediate Similarity	NPC97700
0.8438	Intermediate Similarity	NPC116756
0.8438	Intermediate Similarity	NPC103616

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 NPC57964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	509
0.1-0.2	4157
0.2-0.3	3102
0.3-0.4	748
0.4-0.5	348
0.5-0.6	211
0.6-0.7	51
0.7-0.8	19
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD8171	Discontinued
0.8218	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD8133	Approved
0.7838	Intermediate Similarity	NPD8377	Approved
0.7838	Intermediate Similarity	NPD8294	Approved
0.7768	Intermediate Similarity	NPD8033	Approved
0.7768	Intermediate Similarity	NPD8296	Approved
0.7768	Intermediate Similarity	NPD8380	Approved
0.7768	Intermediate Similarity	NPD8379	Approved
0.7768	Intermediate Similarity	NPD8335	Approved
0.7768	Intermediate Similarity	NPD8378	Approved
0.7609	Intermediate Similarity	NPD6928	Phase 2
0.7589	Intermediate Similarity	NPD7516	Approved
0.757	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.7368	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3669	Approved
0.7273	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6118	Approved
0.7204	Intermediate Similarity	NPD6115	Approved
0.7204	Intermediate Similarity	NPD6114	Approved
0.7204	Intermediate Similarity	NPD6697	Approved
0.7168	Intermediate Similarity	NPD6940	Discontinued
0.7155	Intermediate Similarity	NPD7503	Approved
0.7143	Intermediate Similarity	NPD1810	Approved
0.7143	Intermediate Similarity	NPD1811	Approved
0.7097	Intermediate Similarity	NPD6116	Phase 1
0.7059	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6117	Approved
0.6891	Remote Similarity	NPD8328	Phase 3
0.6885	Remote Similarity	NPD7319	Approved
0.6813	Remote Similarity	NPD2254	Approved
0.6813	Remote Similarity	NPD2686	Approved
0.6813	Remote Similarity	NPD2687	Approved
0.6774	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7991	Discontinued
0.6757	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD7736	Approved
0.6635	Remote Similarity	NPD8034	Phase 2
0.6635	Remote Similarity	NPD8035	Phase 2
0.6633	Remote Similarity	NPD1779	Approved
0.6633	Remote Similarity	NPD1780	Approved
0.6549	Remote Similarity	NPD8174	Phase 2
0.6549	Remote Similarity	NPD6686	Approved
0.6517	Remote Similarity	NPD371	Approved
0.6452	Remote Similarity	NPD8293	Discontinued
0.6404	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD3703	Phase 2
0.6354	Remote Similarity	NPD3702	Approved
0.6324	Remote Similarity	NPD7625	Phase 1
0.6277	Remote Similarity	NPD4787	Phase 1
0.6273	Remote Similarity	NPD7638	Approved
0.626	Remote Similarity	NPD6370	Approved
0.6216	Remote Similarity	NPD7639	Approved
0.6216	Remote Similarity	NPD7640	Approved
0.6207	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7525	Registered
0.6186	Remote Similarity	NPD6882	Approved
0.6186	Remote Similarity	NPD8297	Approved
0.6179	Remote Similarity	NPD8513	Phase 3
0.6179	Remote Similarity	NPD8516	Approved
0.6179	Remote Similarity	NPD8517	Approved
0.6179	Remote Similarity	NPD8515	Approved
0.617	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD1700	Approved
0.616	Remote Similarity	NPD7492	Approved
0.6116	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD6616	Approved
0.6106	Remote Similarity	NPD7632	Discontinued
0.6098	Remote Similarity	NPD6054	Approved
0.6098	Remote Similarity	NPD6319	Approved
0.6098	Remote Similarity	NPD6059	Approved
0.6077	Remote Similarity	NPD8449	Approved
0.6071	Remote Similarity	NPD8418	Phase 2
0.6064	Remote Similarity	NPD5360	Phase 3
0.6064	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD7078	Approved
0.6042	Remote Similarity	NPD6081	Approved
0.6042	Remote Similarity	NPD5777	Approved
0.6031	Remote Similarity	NPD8450	Suspended
0.6017	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD8084	Approved
0.5965	Remote Similarity	NPD8086	Approved
0.5965	Remote Similarity	NPD8083	Approved
0.5965	Remote Similarity	NPD8139	Approved
0.5965	Remote Similarity	NPD8082	Approved
0.5965	Remote Similarity	NPD8085	Approved
0.5965	Remote Similarity	NPD8138	Approved
0.5948	Remote Similarity	NPD6402	Approved
0.5948	Remote Similarity	NPD6675	Approved
0.5948	Remote Similarity	NPD7128	Approved
0.5948	Remote Similarity	NPD5739	Approved
0.5943	Remote Similarity	NPD7524	Approved
0.5938	Remote Similarity	NPD4244	Approved
0.5938	Remote Similarity	NPD4245	Approved
0.5938	Remote Similarity	NPD4789	Approved
0.5932	Remote Similarity	NPD6372	Approved
0.5932	Remote Similarity	NPD6373	Approved
0.592	Remote Similarity	NPD6015	Approved
0.592	Remote Similarity	NPD6016	Approved
0.592	Remote Similarity	NPD6921	Approved
0.5913	Remote Similarity	NPD8276	Approved
0.5913	Remote Similarity	NPD8275	Approved
0.5909	Remote Similarity	NPD7748	Approved
0.5897	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7902	Approved
0.5873	Remote Similarity	NPD5988	Approved
0.5862	Remote Similarity	NPD8081	Approved
0.5854	Remote Similarity	NPD7115	Discovery
0.5851	Remote Similarity	NPD4224	Phase 2
0.5847	Remote Similarity	NPD6899	Approved
0.5847	Remote Similarity	NPD6881	Approved
0.5847	Remote Similarity	NPD7320	Approved
0.5833	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD3698	Phase 2
0.5833	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8130	Phase 1
0.5833	Remote Similarity	NPD6649	Approved
0.5827	Remote Similarity	NPD6067	Discontinued
0.5824	Remote Similarity	NPD6123	Approved
0.5818	Remote Similarity	NPD6399	Phase 3
0.5812	Remote Similarity	NPD8393	Approved
0.5784	Remote Similarity	NPD7645	Phase 2
0.5763	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD5697	Approved
0.5763	Remote Similarity	NPD5701	Approved
0.5763	Remote Similarity	NPD8140	Approved
0.5763	Remote Similarity	NPD8307	Discontinued
0.575	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD7102	Approved
0.575	Remote Similarity	NPD7290	Approved
0.5745	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7515	Phase 2
0.5714	Remote Similarity	NPD4758	Discontinued
0.5703	Remote Similarity	NPD7604	Phase 2
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.5701	Remote Similarity	NPD8308	Discontinued
0.5686	Remote Similarity	NPD3671	Phase 1
0.5686	Remote Similarity	NPD5364	Discontinued
0.5669	Remote Similarity	NPD5983	Phase 2
0.5667	Remote Similarity	NPD8306	Approved
0.5667	Remote Similarity	NPD8305	Approved
0.5667	Remote Similarity	NPD6012	Approved
0.5667	Remote Similarity	NPD6013	Approved
0.5667	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD6033	Approved
0.5641	Remote Similarity	NPD7912	Approved
0.5641	Remote Similarity	NPD7986	Approved
0.5641	Remote Similarity	NPD7987	Approved
0.5641	Remote Similarity	NPD7911	Approved
0.5636	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6700	Approved
0.5631	Remote Similarity	NPD7329	Approved
0.5625	Remote Similarity	NPD7900	Approved
0.5625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.562	Remote Similarity	NPD8087	Discontinued
0.5615	Remote Similarity	NPD6336	Discontinued
0.5614	Remote Similarity	NPD6084	Phase 2
0.5614	Remote Similarity	NPD6083	Phase 2
0.5603	Remote Similarity	NPD5344	Discontinued

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