NPASS Compound

Structure

NPC24435 OpenBabel07101718242D 48 55 0 0 1 0 0 0 0 0999 V2000 2.5250 -3.5531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2040 -5.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3173 -2.5749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3663 -2.2656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7145 -3.3926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3280 -2.6253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9522 0.2387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8579 1.8694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9370 -4.3675 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6230 -2.9346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4476 -2.7124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5356 -1.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4896 0.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3276 1.5018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9532 -0.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2776 1.7314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2299 -2.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4866 -1.3379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9137 0.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3330 0.9053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4919 -0.7214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0237 1.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1809 -1.6976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6943 -0.3597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9385 -0.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6336 0.7203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3886 -0.7194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6453 -0.0505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8843 -1.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9510 0.3092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1349 -2.9822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2077 -0.9782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4678 -1.4484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2748 1.0087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7743 -2.6130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2096 -3.9794 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.1587 -1.2874 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.8926 -4.6623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8307 -3.9128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7104 1.5816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2246 1.9438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8549 -0.7845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6470 2.5076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3539 -1.9119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6395 1.7810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6005 -3.1763 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7433 0.6690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 2 1 6 0 0 0 9 39 1 0 0 0 0 10 40 1 1 0 0 0 11 17 2 0 0 0 0 11 31 1 0 0 0 0 12 18 2 0 0 0 0 12 32 1 0 0 0 0 13 19 1 0 0 0 0 13 41 1 0 0 0 0 14 20 1 0 0 0 0 14 42 1 0 0 0 0 15 21 2 0 0 0 0 15 43 1 0 0 0 0 16 22 2 0 0 0 0 16 44 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 19 25 2 0 0 0 0 20 26 2 0 0 0 0 21 25 1 0 0 0 0 21 33 1 0 0 0 0 22 26 1 0 0 0 0 22 34 1 0 0 0 0 23 27 1 0 0 0 0 23 29 2 0 0 0 0 24 28 1 0 0 0 0 24 30 2 0 0 0 0 25 27 1 0 0 0 0 26 28 1 0 0 0 0 27 28 2 0 0 0 0 29 33 1 0 0 0 0 29 35 1 0 0 0 0 30 34 1 0 0 0 0 30 36 1 0 0 0 0 31 35 2 0 0 0 0 31 37 1 0 0 0 0 32 36 2 0 0 0 0 32 38 1 0 0 0 0 33 45 2 0 0 0 0 34 46 2 0 0 0 0 35 47 1 0 0 0 0 36 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	775.99
Volume:	649.683
LogP:	7.95
LogD:	2.171
LogS:	-8.046
# Rotatable Bonds:	6
TPSA:	195.98
# H-Bond Aceptor:	10
# H-Bond Donor:	8
# Rings:	8
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.067
Synthetic Accessibility Score:	4.743
Fsp3:	0.222
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.894
MDCK Permeability:	8.55445432534907e-06
Pgp-inhibitor:	0.896
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.986
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	95.1032485961914%
Volume Distribution (VD):	0.548
Pgp-substrate:	6.613440036773682%

ADMET: Metabolism

CYP1A2-inhibitor:	0.57
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.696
CYP2C9-substrate:	0.735
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.479
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.934
Carcinogencity:	0.213
Eye Corrosion:	0.004
Eye Irritation:	0.889
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC24435

Natural Product ID:	NPC24435
*Common Name:**	Gymnochrome E
IUPAC Name:	n.a.
Synonyms:	Gymnochrome E
Standard InCHIKey:	FQXGDTNOEQJUMM-VHSXEESVSA-N
Standard InCHI:	InChI=1S/C36H26Br2O10/c1-3-4-10(40)6-12-18-17-11(5-9(2)39)31(37)35(47)29-23(17)27-25-19(13(41)7-15(43)21(25)33(29)45)20-14(42)8-16(44)22-26(20)28(27)24(18)30(34(22)46)36(48)32(12)38/h7-10,39-44,47-48H,3-6H2,1-2H3/t9-,10+/m0/s1
SMILES:	CCC[C@H](Cc1c(Br)c(O)c2c3c1c1c(C[C@@H](O)C)c(Br)c(c4c1c1c3c3c(C2=O)c(O)cc(c3c2c1c(C4=O)c(O)cc2O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094577
PubChem CID:	46211781
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0001851] Pyrenes [CHEMONTID:0000316] Benzopyrenes

*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
NPO13709	Holopus rangii	Species	Holopodidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20158243]
NPO13709	Holopus rangii	Species	Holopodidae	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
MIC	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	IC50	=	3500.0	nM	PMID[474753]
NPT684	Individual Protein	Histone deacetylase 1	Homo sapiens	IC50	=	10900.0	nM	PMID[474753]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[474753]

☑ 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 NPC24435 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	475
0.1-0.2	2037
0.2-0.3	4971
0.3-0.4	12836
0.4-0.5	7066
0.5-0.6	6854
0.6-0.7	7399
0.7-0.8	1037
0.8-0.85	17
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC203426
0.8696	High Similarity	NPC477221
0.8688	High Similarity	NPC290194
0.8538	High Similarity	NPC470567
0.85	High Similarity	NPC227841
0.848	Intermediate Similarity	NPC470566
0.8344	Intermediate Similarity	NPC37709
0.8323	Intermediate Similarity	NPC293545
0.8323	Intermediate Similarity	NPC174905
0.821	Intermediate Similarity	NPC295712
0.821	Intermediate Similarity	NPC474203
0.821	Intermediate Similarity	NPC451542
0.821	Intermediate Similarity	NPC296752
0.821	Intermediate Similarity	NPC313047
0.8148	Intermediate Similarity	NPC474961
0.811	Intermediate Similarity	NPC12402
0.8049	Intermediate Similarity	NPC10764
0.8046	Intermediate Similarity	NPC469664
0.8037	Intermediate Similarity	NPC135524
0.8037	Intermediate Similarity	NPC85310
0.8023	Intermediate Similarity	NPC470342
0.8023	Intermediate Similarity	NPC472060
0.8023	Intermediate Similarity	NPC472052
0.7975	Intermediate Similarity	NPC246638
0.7975	Intermediate Similarity	NPC204045
0.7975	Intermediate Similarity	NPC305845
0.7952	Intermediate Similarity	NPC110882
0.7952	Intermediate Similarity	NPC271944
0.7952	Intermediate Similarity	NPC85393
0.7939	Intermediate Similarity	NPC244691
0.7939	Intermediate Similarity	NPC471906
0.7931	Intermediate Similarity	NPC15374
0.7929	Intermediate Similarity	NPC35
0.7927	Intermediate Similarity	NPC19631
0.7927	Intermediate Similarity	NPC239136
0.7888	Intermediate Similarity	NPC191976
0.7879	Intermediate Similarity	NPC471682
0.7874	Intermediate Similarity	NPC273467
0.7874	Intermediate Similarity	NPC189552
0.7861	Intermediate Similarity	NPC324736
0.7853	Intermediate Similarity	NPC470341
0.7853	Intermediate Similarity	NPC190457
0.7853	Intermediate Similarity	NPC234497
0.7853	Intermediate Similarity	NPC472058
0.7853	Intermediate Similarity	NPC105414
0.7853	Intermediate Similarity	NPC324522
0.784	Intermediate Similarity	NPC44960
0.784	Intermediate Similarity	NPC474110
0.7836	Intermediate Similarity	NPC472211
0.7833	Intermediate Similarity	NPC477992
0.7833	Intermediate Similarity	NPC477991
0.7821	Intermediate Similarity	NPC477836
0.7818	Intermediate Similarity	NPC469520
0.7818	Intermediate Similarity	NPC257644
0.7816	Intermediate Similarity	NPC186325
0.7816	Intermediate Similarity	NPC312993
0.7812	Intermediate Similarity	NPC267205
0.7797	Intermediate Similarity	NPC477835
0.7784	Intermediate Similarity	NPC471687
0.7784	Intermediate Similarity	NPC34482
0.7784	Intermediate Similarity	NPC471683
0.7771	Intermediate Similarity	NPC18380
0.7759	Intermediate Similarity	NPC177650
0.7744	Intermediate Similarity	NPC242994
0.7744	Intermediate Similarity	NPC138099
0.7738	Intermediate Similarity	NPC470570
0.7738	Intermediate Similarity	NPC143685
0.773	Intermediate Similarity	NPC471905
0.7727	Intermediate Similarity	NPC315772
0.7725	Intermediate Similarity	NPC48762
0.7714	Intermediate Similarity	NPC292863
0.7714	Intermediate Similarity	NPC184326
0.7711	Intermediate Similarity	NPC137649
0.7702	Intermediate Similarity	NPC314048
0.7697	Intermediate Similarity	NPC169452
0.7697	Intermediate Similarity	NPC181560
0.7688	Intermediate Similarity	NPC226656
0.7688	Intermediate Similarity	NPC266469
0.7688	Intermediate Similarity	NPC66508
0.7684	Intermediate Similarity	NPC290160
0.7683	Intermediate Similarity	NPC87723
0.767	Intermediate Similarity	NPC472261
0.767	Intermediate Similarity	NPC137232
0.7669	Intermediate Similarity	NPC254847
0.7661	Intermediate Similarity	NPC477914
0.7657	Intermediate Similarity	NPC51760
0.7657	Intermediate Similarity	NPC228654
0.7657	Intermediate Similarity	NPC195167
0.7657	Intermediate Similarity	NPC18699
0.7657	Intermediate Similarity	NPC55443
0.7654	Intermediate Similarity	NPC472262
0.7654	Intermediate Similarity	NPC161964
0.7654	Intermediate Similarity	NPC287604
0.7651	Intermediate Similarity	NPC106519
0.7651	Intermediate Similarity	NPC110810
0.7651	Intermediate Similarity	NPC91019
0.764	Intermediate Similarity	NPC472051
0.764	Intermediate Similarity	NPC472057
0.7636	Intermediate Similarity	NPC143438
0.7633	Intermediate Similarity	NPC472134
0.7633	Intermediate Similarity	NPC314437
0.763	Intermediate Similarity	NPC182921
0.763	Intermediate Similarity	NPC218870
0.763	Intermediate Similarity	NPC474824
0.763	Intermediate Similarity	NPC470408
0.7627	Intermediate Similarity	NPC472059
0.7622	Intermediate Similarity	NPC53206
0.7622	Intermediate Similarity	NPC53414
0.7622	Intermediate Similarity	NPC53001
0.7619	Intermediate Similarity	NPC21599
0.7619	Intermediate Similarity	NPC160839
0.7619	Intermediate Similarity	NPC193703
0.7616	Intermediate Similarity	NPC470569
0.7611	Intermediate Similarity	NPC264063
0.7611	Intermediate Similarity	NPC469486
0.7605	Intermediate Similarity	NPC193555
0.76	Intermediate Similarity	NPC208258
0.7598	Intermediate Similarity	NPC293312
0.7593	Intermediate Similarity	NPC139074
0.7593	Intermediate Similarity	NPC213485
0.7593	Intermediate Similarity	NPC40524
0.7588	Intermediate Similarity	NPC34802
0.7586	Intermediate Similarity	NPC318270
0.7586	Intermediate Similarity	NPC66029
0.7584	Intermediate Similarity	NPC472053
0.7582	Intermediate Similarity	NPC470333
0.7578	Intermediate Similarity	NPC474517
0.7578	Intermediate Similarity	NPC72669
0.7574	Intermediate Similarity	NPC170055
0.7572	Intermediate Similarity	NPC43345
0.7571	Intermediate Similarity	NPC219686
0.7571	Intermediate Similarity	NPC301256
0.7571	Intermediate Similarity	NPC312273
0.7561	Intermediate Similarity	NPC118919
0.7558	Intermediate Similarity	NPC280295
0.7558	Intermediate Similarity	NPC205766
0.7558	Intermediate Similarity	NPC470568
0.7558	Intermediate Similarity	NPC147735
0.7546	Intermediate Similarity	NPC282780
0.7546	Intermediate Similarity	NPC166480
0.7546	Intermediate Similarity	NPC12070
0.7545	Intermediate Similarity	NPC187843
0.7544	Intermediate Similarity	NPC142846
0.7544	Intermediate Similarity	NPC221352
0.7543	Intermediate Similarity	NPC474861
0.7529	Intermediate Similarity	NPC285122
0.7528	Intermediate Similarity	NPC473012
0.7527	Intermediate Similarity	NPC473717
0.7527	Intermediate Similarity	NPC473631
0.7527	Intermediate Similarity	NPC475662
0.7527	Intermediate Similarity	NPC293227
0.7516	Intermediate Similarity	NPC147757
0.7515	Intermediate Similarity	NPC48130
0.7515	Intermediate Similarity	NPC300684
0.7515	Intermediate Similarity	NPC218866
0.7515	Intermediate Similarity	NPC62272
0.7515	Intermediate Similarity	NPC477913
0.7515	Intermediate Similarity	NPC84568
0.7514	Intermediate Similarity	NPC149526
0.7514	Intermediate Similarity	NPC232645
0.7514	Intermediate Similarity	NPC476553
0.7514	Intermediate Similarity	NPC300307
0.7514	Intermediate Similarity	NPC72958
0.7514	Intermediate Similarity	NPC476552
0.7514	Intermediate Similarity	NPC476506
0.7514	Intermediate Similarity	NPC476551
0.7514	Intermediate Similarity	NPC474417
0.75	Intermediate Similarity	NPC130899
0.75	Intermediate Similarity	NPC249272
0.75	Intermediate Similarity	NPC257166
0.75	Intermediate Similarity	NPC317580
0.75	Intermediate Similarity	NPC475184
0.75	Intermediate Similarity	NPC61153
0.75	Intermediate Similarity	NPC251336
0.75	Intermediate Similarity	NPC283590
0.75	Intermediate Similarity	NPC73061
0.75	Intermediate Similarity	NPC329933
0.75	Intermediate Similarity	NPC70859
0.7486	Intermediate Similarity	NPC182555
0.7486	Intermediate Similarity	NPC79375
0.7486	Intermediate Similarity	NPC300668
0.7486	Intermediate Similarity	NPC134171
0.7486	Intermediate Similarity	NPC186227
0.7486	Intermediate Similarity	NPC265624
0.7486	Intermediate Similarity	NPC470336
0.7486	Intermediate Similarity	NPC254351
0.7486	Intermediate Similarity	NPC159707
0.7486	Intermediate Similarity	NPC131862
0.7486	Intermediate Similarity	NPC470335
0.7486	Intermediate Similarity	NPC14606
0.7486	Intermediate Similarity	NPC158027
0.7486	Intermediate Similarity	NPC52611
0.7486	Intermediate Similarity	NPC66441
0.7486	Intermediate Similarity	NPC121649
0.7486	Intermediate Similarity	NPC248739
0.7486	Intermediate Similarity	NPC215203
0.7486	Intermediate Similarity	NPC473009
0.7486	Intermediate Similarity	NPC37253
0.7486	Intermediate Similarity	NPC150908
0.7486	Intermediate Similarity	NPC100049

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 NPC24435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	1125
0.2-0.3	2020
0.3-0.4	3287
0.4-0.5	1577
0.5-0.6	540
0.6-0.7	173
0.7-0.8	9
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
0.85	High Similarity	NPD7390	Discontinued
0.7977	Intermediate Similarity	NPD6959	Discontinued
0.7669	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5408	Approved
0.7515	Intermediate Similarity	NPD5404	Approved
0.7515	Intermediate Similarity	NPD5405	Approved
0.7515	Intermediate Similarity	NPD5406	Approved
0.7471	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6232	Discontinued
0.7213	Intermediate Similarity	NPD7473	Discontinued
0.7191	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4287	Approved
0.7062	Intermediate Similarity	NPD4380	Phase 2
0.7039	Intermediate Similarity	NPD7819	Suspended
0.6973	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6166	Phase 2
0.6973	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7768	Phase 2
0.6957	Remote Similarity	NPD1201	Approved
0.6952	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4288	Approved
0.689	Remote Similarity	NPD1470	Approved
0.6875	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2533	Approved
0.6875	Remote Similarity	NPD2534	Approved
0.6875	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2532	Approved
0.6872	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8151	Discontinued
0.6859	Remote Similarity	NPD8313	Approved
0.6859	Remote Similarity	NPD8312	Approved
0.6833	Remote Similarity	NPD7411	Suspended
0.6813	Remote Similarity	NPD2296	Approved
0.6805	Remote Similarity	NPD943	Approved
0.6772	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6559	Discontinued
0.6753	Remote Similarity	NPD8150	Discontinued
0.6744	Remote Similarity	NPD1510	Phase 2
0.6725	Remote Similarity	NPD1607	Approved
0.6703	Remote Similarity	NPD1934	Approved
0.6702	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7870	Phase 2
0.6667	Remote Similarity	NPD7871	Phase 2
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7075	Discontinued
0.6649	Remote Similarity	NPD7074	Phase 3
0.6649	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3749	Approved
0.6648	Remote Similarity	NPD7003	Approved
0.6647	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6534	Approved
0.6633	Remote Similarity	NPD6535	Approved
0.6629	Remote Similarity	NPD1549	Phase 2
0.6629	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7699	Phase 2
0.6617	Remote Similarity	NPD7700	Phase 2
0.6612	Remote Similarity	NPD6801	Discontinued
0.6608	Remote Similarity	NPD1240	Approved
0.6597	Remote Similarity	NPD7054	Approved
0.6595	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7472	Approved
0.6552	Remote Similarity	NPD6780	Approved
0.6552	Remote Similarity	NPD6781	Approved
0.6552	Remote Similarity	NPD6779	Approved
0.6552	Remote Similarity	NPD6778	Approved
0.6552	Remote Similarity	NPD6777	Approved
0.6552	Remote Similarity	NPD6782	Approved
0.6552	Remote Similarity	NPD6776	Approved
0.6546	Remote Similarity	NPD7808	Phase 3
0.6538	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3226	Approved
0.6537	Remote Similarity	NPD7696	Phase 3
0.6537	Remote Similarity	NPD7697	Approved
0.6537	Remote Similarity	NPD7698	Approved
0.6528	Remote Similarity	NPD6797	Phase 2
0.6514	Remote Similarity	NPD2796	Approved
0.6514	Remote Similarity	NPD2935	Discontinued
0.6505	Remote Similarity	NPD8320	Phase 1
0.6505	Remote Similarity	NPD8319	Approved
0.6495	Remote Similarity	NPD7251	Discontinued
0.6489	Remote Similarity	NPD5494	Approved
0.6486	Remote Similarity	NPD2801	Approved
0.6486	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3818	Discontinued
0.6456	Remote Similarity	NPD7435	Discontinued
0.6448	Remote Similarity	NPD7458	Discontinued
0.6444	Remote Similarity	NPD1511	Approved
0.6437	Remote Similarity	NPD6651	Approved
0.6421	Remote Similarity	NPD5710	Approved
0.6421	Remote Similarity	NPD5711	Approved
0.6418	Remote Similarity	NPD6212	Phase 3
0.6418	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6213	Phase 3
0.6411	Remote Similarity	NPD7701	Phase 2
0.6404	Remote Similarity	NPD2800	Approved
0.6398	Remote Similarity	NPD7783	Phase 2
0.6398	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD1164	Approved
0.6389	Remote Similarity	NPD3300	Phase 2
0.6374	Remote Similarity	NPD1512	Approved
0.6369	Remote Similarity	NPD3750	Approved
0.6364	Remote Similarity	NPD3817	Phase 2
0.6351	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7874	Approved
0.6344	Remote Similarity	NPD37	Approved
0.633	Remote Similarity	NPD3882	Suspended
0.6329	Remote Similarity	NPD6823	Phase 2
0.6324	Remote Similarity	NPD6599	Discontinued
0.6321	Remote Similarity	NPD7801	Approved
0.6319	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.631	Remote Similarity	NPD1465	Phase 2
0.6294	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD2346	Discontinued
0.6289	Remote Similarity	NPD7177	Discontinued
0.6278	Remote Similarity	NPD8166	Discontinued
0.6277	Remote Similarity	NPD5402	Approved
0.6277	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD6020	Phase 2
0.625	Remote Similarity	NPD3787	Discontinued
0.6243	Remote Similarity	NPD4965	Approved
0.6243	Remote Similarity	NPD4966	Approved
0.6243	Remote Similarity	NPD4967	Phase 2
0.6238	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD6099	Approved
0.6236	Remote Similarity	NPD6100	Approved
0.6228	Remote Similarity	NPD3019	Approved
0.6223	Remote Similarity	NPD8455	Phase 2
0.6212	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.621	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD3751	Discontinued
0.6205	Remote Similarity	NPD7228	Approved
0.6188	Remote Similarity	NPD7654	Discontinued
0.6188	Remote Similarity	NPD3400	Discontinued
0.6182	Remote Similarity	NPD405	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD6234	Discontinued
0.6175	Remote Similarity	NPD6799	Approved
0.6168	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6166	Remote Similarity	NPD7229	Phase 3
0.6165	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD920	Approved
0.6162	Remote Similarity	NPD5403	Approved
0.6146	Remote Similarity	NPD4363	Phase 3
0.6146	Remote Similarity	NPD4360	Phase 2
0.6146	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD1551	Phase 2
0.6132	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5028	Approved
0.6131	Remote Similarity	NPD5034	Approved
0.6131	Remote Similarity	NPD4954	Approved
0.6131	Remote Similarity	NPD36	Approved
0.6131	Remote Similarity	NPD4955	Approved
0.6131	Remote Similarity	NPD5026	Approved
0.6131	Remote Similarity	NPD2932	Approved
0.6114	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD3764	Approved
0.6111	Remote Similarity	NPD2344	Approved
0.6111	Remote Similarity	NPD5953	Discontinued
0.6108	Remote Similarity	NPD6273	Approved
0.6102	Remote Similarity	NPD230	Phase 1
0.61	Remote Similarity	NPD5035	Approved
0.6099	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD4628	Phase 3
0.6091	Remote Similarity	NPD7286	Phase 2
0.6089	Remote Similarity	NPD3748	Approved
0.6089	Remote Similarity	NPD5038	Approved
0.6089	Remote Similarity	NPD5037	Approved
0.608	Remote Similarity	NPD5030	Phase 2
0.6077	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6190	Approved
0.6057	Remote Similarity	NPD4625	Phase 3
0.6057	Remote Similarity	NPD7008	Discontinued
0.6054	Remote Similarity	NPD5401	Approved
0.6051	Remote Similarity	NPD3926	Phase 2
0.6049	Remote Similarity	NPD4750	Phase 3
0.6044	Remote Similarity	NPD1243	Approved
0.604	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5036	Approved
0.6031	Remote Similarity	NPD7199	Phase 2
0.6025	Remote Similarity	NPD2342	Discontinued
0.6023	Remote Similarity	NPD9269	Phase 2
0.6012	Remote Similarity	NPD3094	Phase 2
0.6011	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4908	Phase 1
0.6	Remote Similarity	NPD2799	Discontinued
0.6	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5039	Approved
0.5989	Remote Similarity	NPD6663	Approved
0.598	Remote Similarity	NPD4956	Approved
0.5978	Remote Similarity	NPD2309	Approved
0.5976	Remote Similarity	NPD9268	Approved
0.5976	Remote Similarity	NPD1651	Approved
0.597	Remote Similarity	NPD8453	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