NPASS Compound

Structure

CID323198 OpenBabel06191716172D 48 51 0 0 1 0 0 0 0 0999 V2000 3.8204 -2.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 0.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3596 -4.8191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3268 0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 -5.8512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1516 1.0321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4264 -5.8848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0955 -5.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4482 -5.6769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7865 -4.1906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 0.0603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0917 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 0.5603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 -1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 -3.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3596 -4.8191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 -2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 -0.6736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4936 -4.3191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -5.7588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9848 -0.1736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3596 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0917 0.0603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1392 -4.7258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2257 -4.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8083 -3.9827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 -4.3191 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4936 -1.4397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8508 -0.6736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3302 -3.3246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 -5.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 -3.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 -5.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 -0.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5871 -2.6554 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 -5.5851 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3083 -3.1166 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 -2.3794 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -5.0851 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.9577 0.5603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 -5.8512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8204 -3.5530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3268 -6.5248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3268 0.7660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4936 0.0924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 6 41 1 0 0 0 0 7 47 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 26 2 0 0 0 0 11 28 2 0 0 0 0 12 14 1 0 0 0 0 12 24 2 0 0 0 0 13 15 2 0 0 0 0 13 24 1 0 0 0 0 14 25 2 0 0 0 0 15 25 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 27 1 0 0 0 0 20 2 1 6 0 0 0 20 23 1 0 0 0 0 21 3 1 6 0 0 0 21 33 1 0 0 0 0 22 4 1 1 0 0 0 22 35 1 0 0 0 0 22 38 1 0 0 0 0 23 5 1 6 0 0 0 23 48 1 0 0 0 0 25 42 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 27 32 2 0 0 0 0 28 39 1 0 0 0 0 29 18 1 6 0 0 0 29 34 1 0 0 0 0 29 41 1 0 0 0 0 30 24 1 1 0 0 0 30 31 1 0 0 0 0 30 40 1 0 0 0 0 31 36 1 0 0 0 0 31 47 1 6 0 0 0 32 37 1 0 0 0 0 32 39 1 0 0 0 0 33 38 2 3 0 0 0 33 43 1 0 0 0 0 34 40 2 3 0 0 0 34 44 1 0 0 0 0 35 41 1 0 0 0 0 35 45 2 0 0 0 0 36 46 2 0 0 0 0 36 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	680.3
Volume:	686.078
LogP:	4.724
LogD:	4.13
LogS:	-4.127
# Rotatable Bonds:	4
TPSA:	150.06
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.228
Synthetic Accessibility Score:	5.337
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.971
MDCK Permeability:	7.918666597106494e-06
Pgp-inhibitor:	0.986
Pgp-substrate:	0.469
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.079

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	98.5486831665039%
Volume Distribution (VD):	0.574
Pgp-substrate:	1.3418018817901611%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.474
CYP2C19-substrate:	0.208
CYP2C9-inhibitor:	0.773
CYP2C9-substrate:	0.256
CYP2D6-inhibitor:	0.113
CYP2D6-substrate:	0.315
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.642

ADMET: Excretion

Clearance (CL):	3.562
Half-life (T1/2):	0.226

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.447
Maximum Recommended Daily Dose:	0.552
Skin Sensitization:	0.028
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.179

Download Data

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

Natural Product: NPC323198

Natural Product ID:	NPC323198
*Common Name:**	Chondramide B
IUPAC Name:	(3S,4S,7R,10S,13S,15E,17R,18R)-7-[(2-chloro-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-3-methoxy-8,10,13,15,17,18-hexamethyl-1-oxa-5,8,11-triazacyclooctadec-15-ene-2,6,9,12-tetrone
Synonyms:
Standard InCHIKey:	SRZJEPUYAKAFIE-KCQCJHCESA-N
Standard InCHI:	InChI=1S/C36H45ClN4O7/c1-19-16-20(2)23(5)48-36(46)31(47-7)30(24-12-14-25(42)15-13-24)40-34(44)29(18-27-26-10-8-9-11-28(26)39-32(27)37)41(6)35(45)22(4)38-33(43)21(3)17-19/h8-16,20-23,29-31,39,42H,17-18H2,1-7H3,(H,38,43)(H,40,44)/b19-16+/t20-,21+,22+,23-,29-,30+,31+/m1/s1
SMILES:	CC1CC(=CC(C(OC(=O)C(C(NC(=O)C(N(C(=O)C(NC1=O)C)C)CC2=C(NC3=CC=CC=C32)Cl)C4=CC=C(C=C4)O)OC)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426320
PubChem CID:	73349255
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:0004830] Dipeptides

*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
NPO23558	Chondromyces crocatus	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19171307]
NPO33684	Chondramides crocatus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24020843]
NPO23558	Chondromyces crocatus	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8557566]
NPO23558	Chondromyces crocatus	Species	Polyangiaceae	Bacteria	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	EC50	=	220.0	nM	PMID[488405]

☑ 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 NPC323198 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	322
0.1-0.2	1694
0.2-0.3	11352
0.3-0.4	9477
0.4-0.5	13730
0.5-0.6	3562
0.6-0.7	2178
0.7-0.8	354
0.8-0.85	7
0.85-0.9	19
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9252	High Similarity	NPC323752
0.8972	High Similarity	NPC319232
0.8972	High Similarity	NPC24370
0.893	High Similarity	NPC34580
0.893	High Similarity	NPC304307
0.893	High Similarity	NPC124920
0.893	High Similarity	NPC118559
0.8889	High Similarity	NPC100547
0.8848	High Similarity	NPC95240
0.8848	High Similarity	NPC322135
0.8848	High Similarity	NPC223409
0.8843	High Similarity	NPC261251
0.8807	High Similarity	NPC14288
0.8796	High Similarity	NPC214142
0.8767	High Similarity	NPC321592
0.8767	High Similarity	NPC54803
0.8727	High Similarity	NPC284888
0.8688	High Similarity	NPC245055
0.8688	High Similarity	NPC33064
0.8655	High Similarity	NPC82472
0.8465	Intermediate Similarity	NPC74969
0.8158	Intermediate Similarity	NPC272549
0.8136	Intermediate Similarity	NPC314882
0.8051	Intermediate Similarity	NPC181081
0.8018	Intermediate Similarity	NPC326363
0.7965	Intermediate Similarity	NPC184680
0.7931	Intermediate Similarity	NPC470785
0.792	Intermediate Similarity	NPC125597
0.7892	Intermediate Similarity	NPC303658
0.7887	Intermediate Similarity	NPC306376
0.7883	Intermediate Similarity	NPC330009
0.7879	Intermediate Similarity	NPC325976
0.7878	Intermediate Similarity	NPC315467
0.7854	Intermediate Similarity	NPC470784
0.7854	Intermediate Similarity	NPC478158
0.7851	Intermediate Similarity	NPC478006
0.7838	Intermediate Similarity	NPC478157
0.7835	Intermediate Similarity	NPC220852
0.7788	Intermediate Similarity	NPC476098
0.7788	Intermediate Similarity	NPC473317
0.7773	Intermediate Similarity	NPC478009
0.7735	Intermediate Similarity	NPC285343
0.7735	Intermediate Similarity	NPC28945
0.7723	Intermediate Similarity	NPC469928
0.7692	Intermediate Similarity	NPC314056
0.7662	Intermediate Similarity	NPC194740
0.7655	Intermediate Similarity	NPC281049
0.7631	Intermediate Similarity	NPC478010
0.7619	Intermediate Similarity	NPC478011
0.76	Intermediate Similarity	NPC478013
0.7589	Intermediate Similarity	NPC314176
0.7586	Intermediate Similarity	NPC33949
0.7585	Intermediate Similarity	NPC184225
0.7581	Intermediate Similarity	NPC276517
0.7572	Intermediate Similarity	NPC153400
0.7533	Intermediate Similarity	NPC305984
0.7523	Intermediate Similarity	NPC88008
0.75	Intermediate Similarity	NPC476874
0.748	Intermediate Similarity	NPC478012
0.7478	Intermediate Similarity	NPC54744
0.7467	Intermediate Similarity	NPC315804
0.7467	Intermediate Similarity	NPC313804
0.7457	Intermediate Similarity	NPC21638
0.7448	Intermediate Similarity	NPC475816
0.7444	Intermediate Similarity	NPC270918
0.7434	Intermediate Similarity	NPC75634
0.7424	Intermediate Similarity	NPC473041
0.7415	Intermediate Similarity	NPC89987
0.7412	Intermediate Similarity	NPC322064
0.7412	Intermediate Similarity	NPC152768
0.7412	Intermediate Similarity	NPC148183
0.7411	Intermediate Similarity	NPC39679
0.7409	Intermediate Similarity	NPC315491
0.7409	Intermediate Similarity	NPC45459
0.7409	Intermediate Similarity	NPC249040
0.7406	Intermediate Similarity	NPC474183
0.7401	Intermediate Similarity	NPC469592
0.7401	Intermediate Similarity	NPC471080
0.7401	Intermediate Similarity	NPC74562
0.7401	Intermediate Similarity	NPC316181
0.7401	Intermediate Similarity	NPC151781
0.7388	Intermediate Similarity	NPC14812
0.7384	Intermediate Similarity	NPC473105
0.738	Intermediate Similarity	NPC312645
0.7378	Intermediate Similarity	NPC162860
0.7371	Intermediate Similarity	NPC220851
0.7361	Intermediate Similarity	NPC243716
0.7348	Intermediate Similarity	NPC469594
0.7342	Intermediate Similarity	NPC475720
0.7342	Intermediate Similarity	NPC193761
0.7342	Intermediate Similarity	NPC474192
0.7339	Intermediate Similarity	NPC64216
0.7321	Intermediate Similarity	NPC277350
0.7319	Intermediate Similarity	NPC186351
0.7308	Intermediate Similarity	NPC260909
0.7299	Intermediate Similarity	NPC72980
0.7297	Intermediate Similarity	NPC471944
0.7297	Intermediate Similarity	NPC475506
0.7296	Intermediate Similarity	NPC478141
0.7293	Intermediate Similarity	NPC477979
0.7289	Intermediate Similarity	NPC54420
0.7288	Intermediate Similarity	NPC311906
0.7285	Intermediate Similarity	NPC293917
0.7284	Intermediate Similarity	NPC128115
0.7281	Intermediate Similarity	NPC251036
0.7276	Intermediate Similarity	NPC477630
0.7276	Intermediate Similarity	NPC477635
0.7273	Intermediate Similarity	NPC96321
0.7265	Intermediate Similarity	NPC155143
0.7264	Intermediate Similarity	NPC469896
0.7261	Intermediate Similarity	NPC183407
0.7256	Intermediate Similarity	NPC94752
0.7253	Intermediate Similarity	NPC60621
0.7252	Intermediate Similarity	NPC195461
0.7252	Intermediate Similarity	NPC81654
0.7252	Intermediate Similarity	NPC79129
0.7252	Intermediate Similarity	NPC249150
0.7252	Intermediate Similarity	NPC49196
0.7252	Intermediate Similarity	NPC313985
0.725	Intermediate Similarity	NPC477549
0.7249	Intermediate Similarity	NPC89508
0.7239	Intermediate Similarity	NPC116701
0.7237	Intermediate Similarity	NPC23294
0.7237	Intermediate Similarity	NPC87413
0.7232	Intermediate Similarity	NPC165599
0.7222	Intermediate Similarity	NPC280272
0.722	Intermediate Similarity	NPC195788
0.722	Intermediate Similarity	NPC237901
0.722	Intermediate Similarity	NPC15801
0.7217	Intermediate Similarity	NPC219336
0.7215	Intermediate Similarity	NPC471762
0.7212	Intermediate Similarity	NPC53344
0.7212	Intermediate Similarity	NPC244741
0.7209	Intermediate Similarity	NPC94943
0.7206	Intermediate Similarity	NPC9482
0.72	Intermediate Similarity	NPC470500
0.72	Intermediate Similarity	NPC473376
0.7198	Intermediate Similarity	NPC264285
0.7195	Intermediate Similarity	NPC156704
0.7193	Intermediate Similarity	NPC5145
0.7193	Intermediate Similarity	NPC471304
0.7193	Intermediate Similarity	NPC303951
0.7191	Intermediate Similarity	NPC475271
0.7191	Intermediate Similarity	NPC51388
0.7189	Intermediate Similarity	NPC175474
0.7189	Intermediate Similarity	NPC213629
0.7186	Intermediate Similarity	NPC3207
0.7183	Intermediate Similarity	NPC91179
0.7175	Intermediate Similarity	NPC213308
0.717	Intermediate Similarity	NPC15573
0.717	Intermediate Similarity	NPC183662
0.717	Intermediate Similarity	NPC217372
0.7169	Intermediate Similarity	NPC55493
0.7169	Intermediate Similarity	NPC99666
0.7163	Intermediate Similarity	NPC190007
0.7162	Intermediate Similarity	NPC50503
0.7162	Intermediate Similarity	NPC473640
0.7162	Intermediate Similarity	NPC52557
0.7155	Intermediate Similarity	NPC260434
0.7155	Intermediate Similarity	NPC300114
0.7155	Intermediate Similarity	NPC474701
0.7154	Intermediate Similarity	NPC469734
0.7149	Intermediate Similarity	NPC223791
0.7149	Intermediate Similarity	NPC14877
0.7149	Intermediate Similarity	NPC107077
0.7149	Intermediate Similarity	NPC475350
0.7149	Intermediate Similarity	NPC476116
0.7149	Intermediate Similarity	NPC145178
0.7143	Intermediate Similarity	NPC118228
0.7143	Intermediate Similarity	NPC191382
0.7143	Intermediate Similarity	NPC284685
0.7143	Intermediate Similarity	NPC56109
0.7137	Intermediate Similarity	NPC165964
0.7137	Intermediate Similarity	NPC472099
0.7131	Intermediate Similarity	NPC475844
0.713	Intermediate Similarity	NPC12344
0.713	Intermediate Similarity	NPC241024
0.7123	Intermediate Similarity	NPC473763
0.7123	Intermediate Similarity	NPC117244
0.7117	Intermediate Similarity	NPC70956
0.7117	Intermediate Similarity	NPC243834
0.7116	Intermediate Similarity	NPC212535
0.7114	Intermediate Similarity	NPC81939
0.7112	Intermediate Similarity	NPC476114
0.711	Intermediate Similarity	NPC111602
0.711	Intermediate Similarity	NPC102338
0.711	Intermediate Similarity	NPC196251
0.711	Intermediate Similarity	NPC63199
0.7108	Intermediate Similarity	NPC473800
0.7108	Intermediate Similarity	NPC316110
0.7108	Intermediate Similarity	NPC313587
0.7108	Intermediate Similarity	NPC315893
0.7108	Intermediate Similarity	NPC133609
0.7106	Intermediate Similarity	NPC474896
0.7105	Intermediate Similarity	NPC210828
0.7105	Intermediate Similarity	NPC475910
0.7105	Intermediate Similarity	NPC86834
0.7098	Intermediate Similarity	NPC214428
0.7094	Intermediate Similarity	NPC52254
0.7089	Intermediate Similarity	NPC235885

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 NPC323198 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	511
0.2-0.3	770
0.3-0.4	1328
0.4-0.5	2484
0.5-0.6	2847
0.6-0.7	930
0.7-0.8	95
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8303	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7873	Intermediate Similarity	NPD3243	Approved
0.7833	Intermediate Similarity	NPD8463	Approved
0.7703	Intermediate Similarity	NPD7470	Discontinued
0.7652	Intermediate Similarity	NPD7603	Discontinued
0.7617	Intermediate Similarity	NPD4454	Phase 2
0.7543	Intermediate Similarity	NPD3259	Approved
0.7543	Intermediate Similarity	NPD4328	Approved
0.7512	Intermediate Similarity	NPD7948	Phase 1
0.7489	Intermediate Similarity	NPD4885	Approved
0.7445	Intermediate Similarity	NPD4897	Phase 2
0.7431	Intermediate Similarity	NPD5003	Discontinued
0.7424	Intermediate Similarity	NPD5632	Approved
0.7422	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7548	Discontinued
0.7409	Intermediate Similarity	NPD484	Approved
0.7383	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8356	Approved
0.7344	Intermediate Similarity	NPD7576	Discontinued
0.7331	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3003	Approved
0.7319	Intermediate Similarity	NPD8430	Approved
0.7316	Intermediate Similarity	NPD3258	Approved
0.7311	Intermediate Similarity	NPD4373	Phase 2
0.7308	Intermediate Similarity	NPD8459	Approved
0.7308	Intermediate Similarity	NPD8460	Approved
0.7304	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD8255	Phase 2
0.7261	Intermediate Similarity	NPD5612	Discontinued
0.7257	Intermediate Similarity	NPD2916	Discontinued
0.7257	Intermediate Similarity	NPD4952	Phase 3
0.7253	Intermediate Similarity	NPD5507	Approved
0.7253	Intermediate Similarity	NPD5506	Approved
0.7252	Intermediate Similarity	NPD4601	Approved
0.7252	Intermediate Similarity	NPD4600	Approved
0.725	Intermediate Similarity	NPD7853	Phase 2
0.7244	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7790	Approved
0.7238	Intermediate Similarity	NPD7952	Approved
0.7238	Intermediate Similarity	NPD7951	Approved
0.7238	Intermediate Similarity	NPD7953	Approved
0.7238	Intermediate Similarity	NPD7950	Approved
0.7238	Intermediate Similarity	NPD7791	Approved
0.7238	Intermediate Similarity	NPD7789	Approved
0.722	Intermediate Similarity	NPD8466	Approved
0.722	Intermediate Similarity	NPD8467	Approved
0.722	Intermediate Similarity	NPD8427	Approved
0.722	Intermediate Similarity	NPD8428	Approved
0.722	Intermediate Similarity	NPD8429	Approved
0.722	Intermediate Similarity	NPD8465	Approved
0.7205	Intermediate Similarity	NPD5450	Discontinued
0.72	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7796	Approved
0.7197	Intermediate Similarity	NPD7797	Approved
0.7182	Intermediate Similarity	NPD7944	Discontinued
0.7181	Intermediate Similarity	NPD6376	Discontinued
0.7173	Intermediate Similarity	NPD7730	Approved
0.7173	Intermediate Similarity	NPD7731	Approved
0.7173	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6716	Phase 1
0.7172	Intermediate Similarity	NPD6517	Phase 3
0.7168	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8102	Discontinued
0.716	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8016	Phase 3
0.7156	Intermediate Similarity	NPD6176	Phase 1
0.7155	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1867	Approved
0.7149	Intermediate Similarity	NPD5512	Phase 3
0.7143	Intermediate Similarity	NPD5903	Approved
0.7143	Intermediate Similarity	NPD7780	Approved
0.7143	Intermediate Similarity	NPD5902	Approved
0.7143	Intermediate Similarity	NPD7955	Approved
0.7143	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5559	Phase 2
0.7143	Intermediate Similarity	NPD7956	Approved
0.7143	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3257	Approved
0.7143	Intermediate Similarity	NPD7781	Approved
0.7137	Intermediate Similarity	NPD8322	Phase 2
0.7137	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8093	Discontinued
0.713	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6248	Phase 2
0.713	Intermediate Similarity	NPD6249	Phase 2
0.7124	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7878	Phase 2
0.7124	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8364	Approved
0.7121	Intermediate Similarity	NPD8363	Approved
0.7113	Intermediate Similarity	NPD7824	Approved
0.7112	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD8426	Approved
0.711	Intermediate Similarity	NPD8425	Approved
0.711	Intermediate Similarity	NPD1534	Approved
0.7105	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5658	Approved
0.7101	Intermediate Similarity	NPD7994	Phase 2
0.7094	Intermediate Similarity	NPD7194	Discontinued
0.7093	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7957	Phase 1
0.709	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7271	Approved
0.7087	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7778	Approved
0.7085	Intermediate Similarity	NPD7777	Approved
0.7085	Intermediate Similarity	NPD53	Approved
0.7083	Intermediate Similarity	NPD6962	Phase 2
0.7078	Intermediate Similarity	NPD2564	Approved
0.7078	Intermediate Similarity	NPD2565	Phase 2
0.7072	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6238	Discontinued
0.7066	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7222	Phase 2
0.7061	Intermediate Similarity	NPD7452	Approved
0.7061	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD7453	Approved
0.7056	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1768	Approved
0.7048	Intermediate Similarity	NPD8272	Phase 2
0.7047	Intermediate Similarity	NPD7708	Approved
0.7046	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD7716	Approved
0.7046	Intermediate Similarity	NPD7717	Approved
0.7045	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4086	Phase 1
0.7027	Intermediate Similarity	NPD4602	Approved
0.7025	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7558	Phase 2
0.7022	Intermediate Similarity	NPD4501	Approved
0.7022	Intermediate Similarity	NPD4500	Approved
0.702	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8359	Phase 2
0.7012	Intermediate Similarity	NPD7688	Phase 1
0.7004	Intermediate Similarity	NPD8072	Approved
0.7004	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD7803	Approved
0.7004	Intermediate Similarity	NPD5487	Phase 1
0.7	Intermediate Similarity	NPD4499	Approved
0.6996	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7426	Phase 1
0.6986	Remote Similarity	NPD2383	Phase 1
0.6982	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6985	Discontinued
0.6974	Remote Similarity	NPD8114	Approved
0.6974	Remote Similarity	NPD8115	Approved
0.697	Remote Similarity	NPD7181	Phase 3
0.697	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5596	Phase 2
0.6957	Remote Similarity	NPD8247	Approved
0.6957	Remote Similarity	NPD8246	Approved
0.6953	Remote Similarity	NPD8094	Discontinued
0.6951	Remote Similarity	NPD4418	Discontinued
0.6949	Remote Similarity	NPD6770	Approved
0.6943	Remote Similarity	NPD7001	Phase 3
0.6942	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6665	Discontinued
0.6933	Remote Similarity	NPD7219	Approved
0.6933	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7221	Approved
0.6932	Remote Similarity	NPD5482	Discontinued
0.6926	Remote Similarity	NPD8349	Phase 1
0.692	Remote Similarity	NPD8358	Approved
0.6916	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4511	Phase 1
0.6916	Remote Similarity	NPD7727	Phase 2
0.6916	Remote Similarity	NPD7817	Phase 1
0.6909	Remote Similarity	NPD4948	Discontinued
0.6903	Remote Similarity	NPD2175	Phase 3
0.6903	Remote Similarity	NPD2176	Approved
0.6903	Remote Similarity	NPD2177	Approved
0.6903	Remote Similarity	NPD3814	Phase 1
0.6903	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5901	Discontinued
0.6892	Remote Similarity	NPD7658	Phase 2
0.6892	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7726	Phase 1
0.6888	Remote Similarity	NPD4845	Discontinued
0.6887	Remote Similarity	NPD2844	Phase 3
0.6886	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8073	Approved
0.6881	Remote Similarity	NPD2095	Phase 2
0.6881	Remote Similarity	NPD2092	Phase 2
0.6881	Remote Similarity	NPD2094	Phase 2
0.6878	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8403	Phase 1
0.6867	Remote Similarity	NPD5416	Discontinued
0.6867	Remote Similarity	NPD5066	Phase 2
0.6867	Remote Similarity	NPD5067	Phase 2
0.6866	Remote Similarity	NPD6452	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