NPASS Compound

Structure

CID238945 OpenBabel06191716042D 76 81 0 0 1 0 0 0 0 0999 V2000 -1.3911 -9.4221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1231 -9.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1844 1.5019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5316 -2.5560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8135 -2.1659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6598 -3.0459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5432 -1.5561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8267 -2.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1664 -3.1015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2252 1.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9891 -1.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7996 -2.5358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6831 -1.0460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1929 -2.7772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5326 -3.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7596 1.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1231 -0.7598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6947 0.7193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7812 -2.2380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9511 -1.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9120 -4.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6883 -7.7304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5398 -4.6079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1336 -7.6510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8849 -9.5015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3245 -9.9294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2629 -8.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1976 1.3397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8113 -1.5359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5458 -3.7128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3354 -8.6660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0793 -1.5157 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0545 -6.9569 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5571 -4.4228 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4820 -6.8925 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9252 -4.3241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8988 0.4384 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3799 -1.4290 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8709 -5.5515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1163 -7.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2745 -7.9323 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8447 0.4041 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4647 -2.4385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2592 -5.3774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1597 -6.1572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2127 -7.4967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8745 0.6576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2827 -7.8046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7330 -0.0551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9718 -3.3252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7735 -0.6338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2193 -6.3101 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4474 -6.5223 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.2601 -10.2823 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3710 -8.9305 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7492 -6.2376 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.6269 -3.4253 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.4915 -0.7067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3471 -7.4517 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6496 -5.2854 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2691 -7.8277 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8744 0.6460 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7867 -2.3425 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.5638 2.1132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8536 -5.7366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7680 -8.2244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4260 -2.1629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1727 -5.7842 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9687 -6.7450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6510 -8.3955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7699 1.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0408 -8.7749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2922 0.7740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9693 -3.2555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4928 0.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 29 2 0 0 0 0 13 29 1 0 0 0 0 14 30 2 0 0 0 0 15 30 1 0 0 0 0 18 63 1 0 0 0 0 19 64 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 39 1 0 0 0 0 24 40 1 0 0 0 0 25 31 2 0 0 0 0 25 54 1 0 0 0 0 26 54 2 0 0 0 0 26 55 1 0 0 0 0 28 3 1 1 0 0 0 28 65 1 0 0 0 0 31 55 1 0 0 0 0 32 20 1 6 0 0 0 32 43 1 0 0 0 0 32 58 1 0 0 0 0 33 22 1 6 0 0 0 33 46 1 0 0 0 0 33 56 1 0 0 0 0 34 23 1 6 0 0 0 34 44 1 0 0 0 0 34 57 1 0 0 0 0 35 24 1 6 0 0 0 35 45 1 0 0 0 0 35 59 1 0 0 0 0 36 21 1 6 0 0 0 36 50 1 0 0 0 0 36 60 1 0 0 0 0 37 16 1 6 0 0 0 37 47 1 0 0 0 0 37 63 1 0 0 0 0 38 17 1 6 0 0 0 38 51 1 0 0 0 0 38 64 1 0 0 0 0 39 52 2 0 0 0 0 39 66 1 0 0 0 0 40 53 2 0 0 0 0 40 67 1 0 0 0 0 41 27 1 6 0 0 0 41 48 1 0 0 0 0 41 61 1 0 0 0 0 42 28 1 6 0 0 0 42 49 1 0 0 0 0 42 62 1 0 0 0 0 43 57 2 3 0 0 0 43 68 1 0 0 0 0 44 56 2 3 0 0 0 44 69 1 0 0 0 0 45 60 2 3 0 0 0 45 70 1 0 0 0 0 46 61 2 3 0 0 0 46 71 1 0 0 0 0 47 62 2 3 0 0 0 47 72 1 0 0 0 0 48 59 2 3 0 0 0 48 73 1 0 0 0 0 49 58 2 3 0 0 0 49 74 1 0 0 0 0 50 64 1 0 0 0 0 50 75 2 0 0 0 0 51 63 1 0 0 0 0 51 76 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1053.5
Volume:	1037.661
LogP:	-0.835
LogD:	-0.342
LogS:	-1.595
# Rotatable Bonds:	12
TPSA:	397.85
# H-Bond Aceptor:	25
# H-Bond Donor:	13
# Rings:	6
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.091
Synthetic Accessibility Score:	6.817
Fsp3:	0.49
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:	-4.155
MDCK Permeability:	0.000279511499684304
Pgp-inhibitor:	0.085
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.799
Plasma Protein Binding (PPB):	32.03314208984375%
Volume Distribution (VD):	0.39
Pgp-substrate:	55.25116729736328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.027
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.194
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.689
Half-life (T1/2):	0.709

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.376
Maximum Recommended Daily Dose:	0.565
Skin Sensitization:	0.622
Carcinogencity:	0.217
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC238945

Natural Product ID:	NPC238945
*Common Name:**	Cyclomontanin C
IUPAC Name:	n.a.
Synonyms:	Cyclomontanin C
Standard InCHIKey:	POVFXEIWKRHEKP-GCGRWEQZSA-N
Standard InCHI:	InChI=1S/C51H67N13O12/c1-27(2)41-48(73)59-35(24-40(53)67)45(70)60-36(21-30-14-8-5-9-15-30)50(75)64-19-11-17-38(64)51(76)63-18-10-16-37(63)47(72)62-42(28(3)65)49(74)58-32(20-29-12-6-4-7-13-29)43(68)57-34(23-39(52)66)44(69)56-33(46(71)61-41)22-31-25-54-26-55-31/h4-9,12-15,25-28,32-38,41-42,65H,10-11,16-24H2,1-3H3,(H2,52,66)(H2,53,67)(H,54,55)(H,56,69)(H,57,68)(H,58,74)(H,59,73)(H,60,70)(H,61,71)(H,62,72)/t28-,32+,33+,34+,35+,36+,37+,38+,41+,42+/m1/s1
SMILES:	CC(C)[C@H]1C(=N[C@@H](CC(=N)O)C(=N[C@@H](Cc2ccccc2)C(=O)N2CCC[C@H]2C(=O)N2CCC[C@H]2C(=N[C@@H]([C@@H](C)O)C(=N[C@@H](Cc2ccccc2)C(=N[C@@H](CC(=N)O)C(=N[C@@H](Cc2cnc[nH]2)C(=N1)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505294
PubChem CID:	25018459
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	trunk bark	n.a.	DOI[10.1039/P19820001205]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1039/P19820001205]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568766]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[18687006]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18687006]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13370	Annona montana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13370	Annona montana	Species	Annonaceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1182	Cell Line	J774.A1	Mus musculus	Activity	=	50.0	%	PMID[570115]

☑ 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 NPC238945 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	331
0.1-0.2	2029
0.2-0.3	18253
0.3-0.4	15274
0.4-0.5	3397
0.5-0.6	2573
0.6-0.7	726
0.7-0.8	102
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8545	High Similarity	NPC69843
0.8465	Intermediate Similarity	NPC328924
0.8451	Intermediate Similarity	NPC323244
0.8125	Intermediate Similarity	NPC162860
0.8029	Intermediate Similarity	NPC54420
0.7962	Intermediate Similarity	NPC320968
0.7877	Intermediate Similarity	NPC54981
0.7736	Intermediate Similarity	NPC71238
0.7727	Intermediate Similarity	NPC64216
0.7721	Intermediate Similarity	NPC54744
0.7644	Intermediate Similarity	NPC89987
0.7617	Intermediate Similarity	NPC107077
0.7617	Intermediate Similarity	NPC223791
0.7594	Intermediate Similarity	NPC473376
0.7593	Intermediate Similarity	NPC75634
0.7583	Intermediate Similarity	NPC155143
0.756	Intermediate Similarity	NPC171317
0.7536	Intermediate Similarity	NPC475506
0.7535	Intermediate Similarity	NPC478158
0.7522	Intermediate Similarity	NPC475859
0.7522	Intermediate Similarity	NPC474877
0.7522	Intermediate Similarity	NPC475969
0.75	Intermediate Similarity	NPC281049
0.749	Intermediate Similarity	NPC477633
0.7478	Intermediate Similarity	NPC470730
0.7478	Intermediate Similarity	NPC470729
0.7478	Intermediate Similarity	NPC477175
0.7478	Intermediate Similarity	NPC477176
0.7456	Intermediate Similarity	NPC63279
0.7445	Intermediate Similarity	NPC477177
0.7424	Intermediate Similarity	NPC297642
0.7412	Intermediate Similarity	NPC165743
0.7393	Intermediate Similarity	NPC473640
0.7371	Intermediate Similarity	NPC54537
0.7364	Intermediate Similarity	NPC478157
0.7358	Intermediate Similarity	NPC100321
0.7265	Intermediate Similarity	NPC477714
0.725	Intermediate Similarity	NPC314882
0.7241	Intermediate Similarity	NPC478028
0.7195	Intermediate Similarity	NPC125181
0.7195	Intermediate Similarity	NPC242872
0.7195	Intermediate Similarity	NPC263117
0.7179	Intermediate Similarity	NPC478029
0.7177	Intermediate Similarity	NPC213629
0.7176	Intermediate Similarity	NPC476874
0.7175	Intermediate Similarity	NPC470732
0.7175	Intermediate Similarity	NPC470731
0.7171	Intermediate Similarity	NPC477634
0.7163	Intermediate Similarity	NPC94752
0.7162	Intermediate Similarity	NPC282247
0.7161	Intermediate Similarity	NPC295452
0.7161	Intermediate Similarity	NPC171393
0.7143	Intermediate Similarity	NPC477715
0.7131	Intermediate Similarity	NPC477108
0.7131	Intermediate Similarity	NPC478006
0.7131	Intermediate Similarity	NPC477109
0.7131	Intermediate Similarity	NPC477107
0.7124	Intermediate Similarity	NPC325976
0.7089	Intermediate Similarity	NPC201831
0.7089	Intermediate Similarity	NPC17487
0.7056	Intermediate Similarity	NPC324850
0.7048	Intermediate Similarity	NPC17059
0.7037	Intermediate Similarity	NPC293917
0.7028	Intermediate Similarity	NPC315467
0.7026	Intermediate Similarity	NPC326363
0.7	Intermediate Similarity	NPC19170
0.6996	Remote Similarity	NPC321939
0.6992	Remote Similarity	NPC28945
0.699	Remote Similarity	NPC60537
0.6988	Remote Similarity	NPC314056
0.6964	Remote Similarity	NPC110602
0.6964	Remote Similarity	NPC31385
0.6964	Remote Similarity	NPC75726
0.696	Remote Similarity	NPC475736
0.6947	Remote Similarity	NPC471192
0.6943	Remote Similarity	NPC474896
0.6943	Remote Similarity	NPC473317
0.6936	Remote Similarity	NPC220852
0.6935	Remote Similarity	NPC469898
0.6932	Remote Similarity	NPC478009
0.6932	Remote Similarity	NPC478010
0.6916	Remote Similarity	NPC267811
0.6916	Remote Similarity	NPC313504
0.6913	Remote Similarity	NPC31097
0.6913	Remote Similarity	NPC327095
0.6913	Remote Similarity	NPC312942
0.691	Remote Similarity	NPC297862
0.691	Remote Similarity	NPC191382
0.691	Remote Similarity	NPC56109
0.6905	Remote Similarity	NPC478013
0.6905	Remote Similarity	NPC228835
0.69	Remote Similarity	NPC272174
0.69	Remote Similarity	NPC469901
0.6889	Remote Similarity	NPC471194
0.6889	Remote Similarity	NPC153980
0.6889	Remote Similarity	NPC471193
0.6889	Remote Similarity	NPC6865
0.6888	Remote Similarity	NPC282531
0.6883	Remote Similarity	NPC40455
0.6872	Remote Similarity	NPC477118
0.6872	Remote Similarity	NPC177996
0.6872	Remote Similarity	NPC147983
0.6853	Remote Similarity	NPC125597
0.6853	Remote Similarity	NPC474196
0.6849	Remote Similarity	NPC285343
0.6844	Remote Similarity	NPC477635
0.6844	Remote Similarity	NPC242923
0.6844	Remote Similarity	NPC72956
0.6844	Remote Similarity	NPC477630
0.6842	Remote Similarity	NPC472999
0.684	Remote Similarity	NPC477120
0.684	Remote Similarity	NPC155444
0.6826	Remote Similarity	NPC474195
0.6824	Remote Similarity	NPC24370
0.6824	Remote Similarity	NPC319232
0.6816	Remote Similarity	NPC473003
0.6816	Remote Similarity	NPC14812
0.681	Remote Similarity	NPC476817
0.6797	Remote Similarity	NPC478011
0.6797	Remote Similarity	NPC478012
0.6795	Remote Similarity	NPC476491
0.6791	Remote Similarity	NPC117244
0.6791	Remote Similarity	NPC473763
0.6791	Remote Similarity	NPC210123
0.6786	Remote Similarity	NPC116555
0.6784	Remote Similarity	NPC469903
0.6784	Remote Similarity	NPC229348
0.678	Remote Similarity	NPC473000
0.6779	Remote Similarity	NPC469900
0.6776	Remote Similarity	NPC321708
0.677	Remote Similarity	NPC314176
0.6766	Remote Similarity	NPC156003
0.6751	Remote Similarity	NPC63031
0.6747	Remote Similarity	NPC63109
0.6741	Remote Similarity	NPC323927
0.6734	Remote Similarity	NPC473002
0.6733	Remote Similarity	NPC469902
0.672	Remote Similarity	NPC74619
0.6714	Remote Similarity	NPC11126
0.6712	Remote Similarity	NPC193761
0.6695	Remote Similarity	NPC253987
0.6682	Remote Similarity	NPC91179
0.6667	Remote Similarity	NPC300183
0.6667	Remote Similarity	NPC473310
0.6667	Remote Similarity	NPC66642
0.6667	Remote Similarity	NPC477119
0.6653	Remote Similarity	NPC323752
0.6653	Remote Similarity	NPC477418
0.6653	Remote Similarity	NPC477420
0.6652	Remote Similarity	NPC17305
0.6638	Remote Similarity	NPC315804
0.6638	Remote Similarity	NPC313804
0.6623	Remote Similarity	NPC472285
0.6623	Remote Similarity	NPC79386
0.6622	Remote Similarity	NPC470497
0.6621	Remote Similarity	NPC106235
0.6621	Remote Similarity	NPC239660
0.6621	Remote Similarity	NPC294693
0.662	Remote Similarity	NPC161143
0.6618	Remote Similarity	NPC469904
0.6606	Remote Similarity	NPC201900
0.6604	Remote Similarity	NPC16659
0.6603	Remote Similarity	NPC314603
0.6588	Remote Similarity	NPC473001
0.6586	Remote Similarity	NPC153400
0.6582	Remote Similarity	NPC475258
0.6571	Remote Similarity	NPC469938
0.6569	Remote Similarity	NPC160666
0.6567	Remote Similarity	NPC308906
0.6564	Remote Similarity	NPC314957
0.6564	Remote Similarity	NPC476524
0.656	Remote Similarity	NPC243716
0.6558	Remote Similarity	NPC307396
0.6557	Remote Similarity	NPC248041
0.6557	Remote Similarity	NPC126709
0.6557	Remote Similarity	NPC265710
0.6557	Remote Similarity	NPC283219
0.6556	Remote Similarity	NPC158055
0.6542	Remote Similarity	NPC267078
0.6542	Remote Similarity	NPC935
0.6537	Remote Similarity	NPC313640
0.6532	Remote Similarity	NPC474389
0.6528	Remote Similarity	NPC235684
0.6524	Remote Similarity	NPC49195
0.652	Remote Similarity	NPC1390
0.652	Remote Similarity	NPC62104
0.6516	Remote Similarity	NPC472207
0.6515	Remote Similarity	NPC474357
0.6515	Remote Similarity	NPC70155
0.6513	Remote Similarity	NPC107160
0.6509	Remote Similarity	NPC14113
0.6509	Remote Similarity	NPC84827
0.6509	Remote Similarity	NPC240088
0.6509	Remote Similarity	NPC145885
0.6509	Remote Similarity	NPC473380
0.6497	Remote Similarity	NPC327477
0.6496	Remote Similarity	NPC472846
0.6496	Remote Similarity	NPC250178
0.6493	Remote Similarity	NPC477462
0.6491	Remote Similarity	NPC476525

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 NPC238945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	519
0.2-0.3	984
0.3-0.4	2236
0.4-0.5	2821
0.5-0.6	1900
0.6-0.7	478
0.7-0.8	36
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8551	High Similarity	NPD8271	Discontinued
0.8291	Intermediate Similarity	NPD8641	Approved
0.8279	Intermediate Similarity	NPD8292	Phase 2
0.8211	Intermediate Similarity	NPD8119	Discontinued
0.8116	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD8075	Discontinued
0.8049	Intermediate Similarity	NPD8629	Discontinued
0.8	Intermediate Similarity	NPD8261	Discontinued
0.7915	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD7465	Suspended
0.782	Intermediate Similarity	NPD7981	Discontinued
0.7773	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7773	Intermediate Similarity	NPD7834	Approved
0.7757	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD8113	Phase 2
0.7721	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD8256	Approved
0.7696	Intermediate Similarity	NPD8257	Approved
0.7545	Intermediate Similarity	NPD8105	Discontinued
0.7479	Intermediate Similarity	NPD8250	Phase 2
0.7463	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7970	Approved
0.7387	Intermediate Similarity	NPD3105	Discontinued
0.7318	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2813	Phase 3
0.7293	Intermediate Similarity	NPD8316	Phase 2
0.7293	Intermediate Similarity	NPD8317	Phase 2
0.7277	Intermediate Similarity	NPD5665	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3497	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1249	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8322	Phase 2
0.7143	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7502	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5768	Phase 2
0.7121	Intermediate Similarity	NPD3130	Discontinued
0.711	Intermediate Similarity	NPD8272	Phase 2
0.7103	Intermediate Similarity	NPD2880	Discontinued
0.7059	Intermediate Similarity	NPD6545	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7817	Phase 1
0.7037	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD8169	Discontinued
0.7018	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6268	Phase 1
0.7014	Intermediate Similarity	NPD2443	Approved
0.7014	Intermediate Similarity	NPD2442	Approved
0.7014	Intermediate Similarity	NPD2152	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6164	Phase 2
0.7013	Intermediate Similarity	NPD6165	Phase 2
0.7009	Intermediate Similarity	NPD7944	Discontinued
0.7005	Intermediate Similarity	NPD2604	Approved
0.7005	Intermediate Similarity	NPD4599	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8375	Approved
0.6996	Remote Similarity	NPD7470	Discontinued
0.699	Remote Similarity	NPD2180	Approved
0.6987	Remote Similarity	NPD6718	Discontinued
0.6972	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1731	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7952	Approved
0.6936	Remote Similarity	NPD7790	Approved
0.6936	Remote Similarity	NPD7789	Approved
0.6936	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7953	Approved
0.6936	Remote Similarity	NPD7791	Approved
0.6936	Remote Similarity	NPD7950	Approved
0.6936	Remote Similarity	NPD7951	Approved
0.6923	Remote Similarity	NPD2876	Phase 3
0.6923	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3697	Discontinued
0.6913	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8484	Phase 2
0.691	Remote Similarity	NPD7781	Approved
0.691	Remote Similarity	NPD7780	Approved
0.6906	Remote Similarity	NPD1600	Suspended
0.6906	Remote Similarity	NPD3968	Approved
0.6897	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2411	Approved
0.6872	Remote Similarity	NPD8523	Approved
0.6872	Remote Similarity	NPD3353	Approved
0.6869	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7731	Approved
0.6867	Remote Similarity	NPD7730	Approved
0.6864	Remote Similarity	NPD7415	Suspended
0.6861	Remote Similarity	NPD2824	Phase 2
0.6856	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3042	Approved
0.6853	Remote Similarity	NPD3043	Approved
0.6847	Remote Similarity	NPD2008	Discontinued
0.6838	Remote Similarity	NPD7887	Approved
0.6838	Remote Similarity	NPD7888	Approved
0.683	Remote Similarity	NPD2408	Discontinued
0.6828	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD3041	Approved
0.6816	Remote Similarity	NPD3410	Approved
0.6816	Remote Similarity	NPD3411	Phase 2
0.6812	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD2928	Phase 2
0.6812	Remote Similarity	NPD7297	Phase 2
0.681	Remote Similarity	NPD6752	Phase 1
0.681	Remote Similarity	NPD6753	Phase 1
0.6809	Remote Similarity	NPD7824	Approved
0.6802	Remote Similarity	NPD8442	Discontinued
0.6797	Remote Similarity	NPD4414	Discontinued
0.679	Remote Similarity	NPD8291	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4612	Discontinued
0.6784	Remote Similarity	NPD7689	Approved
0.6781	Remote Similarity	NPD7271	Approved
0.6779	Remote Similarity	NPD8524	Approved
0.6773	Remote Similarity	NPD5461	Discontinued
0.6771	Remote Similarity	NPD3967	Approved
0.6769	Remote Similarity	NPD7471	Discontinued
0.6768	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1030	Approved
0.6768	Remote Similarity	NPD1027	Approved
0.6753	Remote Similarity	NPD6210	Phase 3
0.6753	Remote Similarity	NPD5884	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4155	Approved
0.6743	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD4458	Phase 2
0.6742	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD3840	Phase 2
0.6741	Remote Similarity	NPD1506	Discontinued
0.6741	Remote Similarity	NPD3839	Phase 2
0.6738	Remote Similarity	NPD6849	Phase 2
0.6738	Remote Similarity	NPD6850	Phase 2
0.6731	Remote Similarity	NPD3108	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8525	Approved
0.6724	Remote Similarity	NPD6381	Phase 2
0.6712	Remote Similarity	NPD5486	Discontinued
0.671	Remote Similarity	NPD537	Phase 2
0.671	Remote Similarity	NPD534	Phase 2
0.6699	Remote Similarity	NPD6906	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7618	Phase 3
0.6697	Remote Similarity	NPD7619	Phase 3
0.6696	Remote Similarity	NPD4563	Phase 2
0.6696	Remote Similarity	NPD3915	Approved
0.6696	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2793	Discontinued
0.6681	Remote Similarity	NPD5510	Approved
0.6681	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD8421	Discontinued
0.6667	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3918	Approved
0.6667	Remote Similarity	NPD6035	Phase 2
0.6667	Remote Similarity	NPD3405	Phase 3
0.6667	Remote Similarity	NPD8026	Phase 1
0.6667	Remote Similarity	NPD6470	Phase 3
0.6667	Remote Similarity	NPD3917	Approved
0.6667	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD7486	Phase 1
0.6652	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD5072	Discontinued
0.6651	Remote Similarity	NPD2526	Phase 2
0.6651	Remote Similarity	NPD2523	Phase 2
0.6637	Remote Similarity	NPD6520	Phase 3
0.6637	Remote Similarity	NPD6521	Phase 3
0.6636	Remote Similarity	NPD6664	Approved
0.6623	Remote Similarity	NPD6763	Discontinued
0.6623	Remote Similarity	NPD4863	Approved
0.6622	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5458	Discontinued
0.6621	Remote Similarity	NPD8339	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD3906	Approved
0.6617	Remote Similarity	NPD1303	Phase 1
0.661	Remote Similarity	NPD7711	Discontinued
0.661	Remote Similarity	NPD8289	Discontinued
0.6608	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1982	Phase 1
0.6605	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6595	Phase 3
0.6594	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD2902	Phase 2
0.6593	Remote Similarity	NPD4533	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5017	Discontinued
0.6591	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8321	Discontinued
0.6578	Remote Similarity	NPD7103	Approved
0.6578	Remote Similarity	NPD8114	Approved
0.6578	Remote Similarity	NPD8115	Approved
0.6575	Remote Similarity	NPD460	Discontinued
0.6573	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8408	Discontinued
0.6567	Remote Similarity	NPD5199	Approved
0.6567	Remote Similarity	NPD5198	Approved
0.6565	Remote Similarity	NPD8094	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