NPASS Compound

Structure

NPC472199 OpenBabel07101718332D 49 49 0 0 1 0 0 0 0 0999 V2000 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -6.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 -5.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -7.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 4 21 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 12 19 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 14 26 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 16 25 2 0 0 0 0 17 24 2 0 0 0 0 17 27 1 0 0 0 0 18 39 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 1 0 0 0 21 30 1 0 0 0 0 22 5 1 6 0 0 0 22 31 1 0 0 0 0 23 6 1 6 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 9 1 1 0 0 0 26 36 1 0 0 0 0 27 10 1 1 0 0 0 27 36 1 0 0 0 0 28 11 1 6 0 0 0 28 32 1 0 0 0 0 28 37 1 0 0 0 0 29 18 1 1 0 0 0 29 33 1 0 0 0 0 29 48 1 0 0 0 0 30 40 1 1 0 0 0 31 41 1 1 0 0 0 32 42 1 1 0 0 0 33 34 1 0 0 0 0 33 43 1 6 0 0 0 34 35 1 0 0 0 0 34 44 1 1 0 0 0 35 38 1 0 0 0 0 35 45 1 1 0 0 0 36 49 1 1 0 0 0 37 46 2 0 0 0 0 37 47 1 0 0 0 0 38 48 1 0 0 0 0 38 49 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1210.63
Volume:	1178.385
LogP:	4.817
LogD:	3.528
LogS:	-4.388
# Rotatable Bonds:	21
TPSA:	359.34
# H-Bond Aceptor:	26
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	7.385
Fsp3:	0.931
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:	-5.481
MDCK Permeability:	0.0005747065297327936
Pgp-inhibitor:	0.987
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.824
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.133

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	89.0455093383789%
Volume Distribution (VD):	0.649
Pgp-substrate:	6.490042209625244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.009
CYP3A4-inhibitor:	0.362
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	0.902
Half-life (T1/2):	0.551

ADMET: Toxicity

hERG Blockers:	0.905
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.711
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.669

Download Data

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

Natural Product: NPC472199

Natural Product ID:	NPC472199
*Common Name:**	IXACCXKOOUBCOZ-SMYMJKOMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IXACCXKOOUBCOZ-SMYMJKOMSA-N
Standard InCHI:	InChI=1S/C38H68O11/c1-12-19(2)13-20(3)14-26(9)36(49-38-35(45)34(44)33(43)29(18-39)48-38)27(10)17-24(7)31(41)22(5)15-21(4)30(40)23(6)16-25(8)32(42)28(11)37(46)47/h15-17,19-20,22-23,26-36,38-45H,12-14,18H2,1-11H3,(H,46,47)/b21-15+,24-17+,25-16+/t19-,20-,22-,23-,26-,27-,28+,29+,30+,31-,32+,33+,34-,35-,36+,38-/m0/s1
SMILES:	CC[C@@H](C[C@@H](C[C@@H]([C@H]([C@H](/C=C(/[C@H]([C@H](/C=C(/[C@H]([C@H](/C=C(/[C@H]([C@H](C(=O)O)C)O)C)C)O)C)C)O)C)C)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@@H]1O)O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3344129
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO33169	bionectria ochroleuca	Species	Bionectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302529]

☑ 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
Others	5

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	2400.0	nM	PMID[479560]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	100000.0	nM	PMID[479560]
NPT20	Organism	Candida albicans	Candida albicans	Ratio	=	0.25	n.a.	PMID[479560]
NPT20	Organism	Candida albicans	Candida albicans	MIC=>80	>	100.0	uM	PMID[479560]
NPT20	Organism	Candida albicans	Candida albicans	MIC=>80	=	5.0	uM	PMID[479560]
NPT20	Organism	Candida albicans	Candida albicans	Ratio	<	0.05	n.a.	PMID[479560]
NPT20	Organism	Candida albicans	Candida albicans	FICI	<	0.3	n.a.	PMID[479560]

☑ 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 NPC472199 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	195
0.1-0.2	1219
0.2-0.3	4519
0.3-0.4	9404
0.4-0.5	13781
0.5-0.6	7911
0.6-0.7	4947
0.7-0.8	688
0.8-0.85	22
0.85-0.9	7
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC472198
0.954	High Similarity	NPC472197
0.9	High Similarity	NPC472195
0.9	High Similarity	NPC238090
0.9	High Similarity	NPC472196
0.8977	High Similarity	NPC137368
0.8901	High Similarity	NPC159698
0.8791	High Similarity	NPC320089
0.8478	Intermediate Similarity	NPC9447
0.8409	Intermediate Similarity	NPC69469
0.837	Intermediate Similarity	NPC313670
0.8316	Intermediate Similarity	NPC54731
0.8222	Intermediate Similarity	NPC477747
0.8222	Intermediate Similarity	NPC477746
0.8182	Intermediate Similarity	NPC236649
0.8182	Intermediate Similarity	NPC21693
0.8125	Intermediate Similarity	NPC306041
0.81	Intermediate Similarity	NPC469869
0.8081	Intermediate Similarity	NPC201191
0.8046	Intermediate Similarity	NPC133377
0.8043	Intermediate Similarity	NPC475037
0.8043	Intermediate Similarity	NPC86005
0.8043	Intermediate Similarity	NPC477959
0.8041	Intermediate Similarity	NPC476613
0.8041	Intermediate Similarity	NPC476612
0.8022	Intermediate Similarity	NPC471494
0.802	Intermediate Similarity	NPC476740
0.802	Intermediate Similarity	NPC476738
0.8	Intermediate Similarity	NPC473500
0.8	Intermediate Similarity	NPC478037
0.8	Intermediate Similarity	NPC470313
0.8	Intermediate Similarity	NPC156089
0.8	Intermediate Similarity	NPC38295
0.8	Intermediate Similarity	NPC309398
0.8	Intermediate Similarity	NPC478036
0.7979	Intermediate Similarity	NPC202886
0.7979	Intermediate Similarity	NPC473311
0.7961	Intermediate Similarity	NPC315836
0.7961	Intermediate Similarity	NPC313668
0.7959	Intermediate Similarity	NPC203627
0.7955	Intermediate Similarity	NPC321728
0.7938	Intermediate Similarity	NPC165332
0.7938	Intermediate Similarity	NPC195645
0.7938	Intermediate Similarity	NPC180722
0.7935	Intermediate Similarity	NPC311163
0.7931	Intermediate Similarity	NPC110813
0.7921	Intermediate Similarity	NPC470768
0.7912	Intermediate Similarity	NPC266718
0.7905	Intermediate Similarity	NPC174836
0.7895	Intermediate Similarity	NPC477749
0.7895	Intermediate Similarity	NPC235051
0.7885	Intermediate Similarity	NPC83005
0.7879	Intermediate Similarity	NPC469871
0.7879	Intermediate Similarity	NPC469870
0.7872	Intermediate Similarity	NPC477748
0.7865	Intermediate Similarity	NPC163362
0.7865	Intermediate Similarity	NPC127295
0.7857	Intermediate Similarity	NPC472290
0.7857	Intermediate Similarity	NPC40812
0.783	Intermediate Similarity	NPC264153
0.7826	Intermediate Similarity	NPC475034
0.7826	Intermediate Similarity	NPC470124
0.7822	Intermediate Similarity	NPC475367
0.7822	Intermediate Similarity	NPC474581
0.7822	Intermediate Similarity	NPC473816
0.7812	Intermediate Similarity	NPC61201
0.78	Intermediate Similarity	NPC154127
0.78	Intermediate Similarity	NPC475655
0.78	Intermediate Similarity	NPC57586
0.78	Intermediate Similarity	NPC98859
0.78	Intermediate Similarity	NPC2313
0.78	Intermediate Similarity	NPC20673
0.78	Intermediate Similarity	NPC471637
0.78	Intermediate Similarity	NPC476611
0.78	Intermediate Similarity	NPC4637
0.78	Intermediate Similarity	NPC475157
0.78	Intermediate Similarity	NPC154132
0.7789	Intermediate Similarity	NPC6414
0.7789	Intermediate Similarity	NPC303451
0.7778	Intermediate Similarity	NPC472015
0.7766	Intermediate Similarity	NPC201046
0.7757	Intermediate Similarity	NPC181145
0.7755	Intermediate Similarity	NPC143446
0.7755	Intermediate Similarity	NPC474297
0.7755	Intermediate Similarity	NPC241911
0.7745	Intermediate Similarity	NPC470519
0.7745	Intermediate Similarity	NPC231271
0.7742	Intermediate Similarity	NPC208473
0.7732	Intermediate Similarity	NPC5418
0.7732	Intermediate Similarity	NPC256368
0.7723	Intermediate Similarity	NPC223834
0.7723	Intermediate Similarity	NPC313569
0.7717	Intermediate Similarity	NPC475035
0.7706	Intermediate Similarity	NPC475309
0.77	Intermediate Similarity	NPC255677
0.77	Intermediate Similarity	NPC306344
0.77	Intermediate Similarity	NPC22149
0.77	Intermediate Similarity	NPC244878
0.77	Intermediate Similarity	NPC473146
0.7692	Intermediate Similarity	NPC473807
0.7692	Intermediate Similarity	NPC177524
0.7692	Intermediate Similarity	NPC219900
0.7692	Intermediate Similarity	NPC193765
0.7692	Intermediate Similarity	NPC392
0.7684	Intermediate Similarity	NPC478110
0.767	Intermediate Similarity	NPC470767
0.767	Intermediate Similarity	NPC470763
0.767	Intermediate Similarity	NPC315070
0.7667	Intermediate Similarity	NPC100697
0.7664	Intermediate Similarity	NPC293658
0.7664	Intermediate Similarity	NPC474410
0.7664	Intermediate Similarity	NPC311592
0.7664	Intermediate Similarity	NPC75167
0.7658	Intermediate Similarity	NPC170880
0.7658	Intermediate Similarity	NPC183353
0.7658	Intermediate Similarity	NPC469812
0.7653	Intermediate Similarity	NPC36954
0.7653	Intermediate Similarity	NPC108141
0.7653	Intermediate Similarity	NPC469543
0.7647	Intermediate Similarity	NPC234304
0.7647	Intermediate Similarity	NPC267869
0.7647	Intermediate Similarity	NPC197736
0.7647	Intermediate Similarity	NPC197541
0.7647	Intermediate Similarity	NPC284929
0.7647	Intermediate Similarity	NPC118761
0.7642	Intermediate Similarity	NPC31839
0.7642	Intermediate Similarity	NPC297945
0.7642	Intermediate Similarity	NPC126897
0.7634	Intermediate Similarity	NPC242233
0.7629	Intermediate Similarity	NPC471483
0.7629	Intermediate Similarity	NPC320552
0.7624	Intermediate Similarity	NPC28304
0.7624	Intermediate Similarity	NPC298255
0.7624	Intermediate Similarity	NPC198992
0.7619	Intermediate Similarity	NPC40728
0.7619	Intermediate Similarity	NPC118225
0.7604	Intermediate Similarity	NPC118078
0.76	Intermediate Similarity	NPC255592
0.76	Intermediate Similarity	NPC70733
0.76	Intermediate Similarity	NPC187761
0.76	Intermediate Similarity	NPC477928
0.76	Intermediate Similarity	NPC261377
0.76	Intermediate Similarity	NPC308567
0.76	Intermediate Similarity	NPC151093
0.76	Intermediate Similarity	NPC83895
0.76	Intermediate Similarity	NPC475653
0.76	Intermediate Similarity	NPC56071
0.76	Intermediate Similarity	NPC161855
0.7596	Intermediate Similarity	NPC293512
0.7596	Intermediate Similarity	NPC472390
0.7593	Intermediate Similarity	NPC472274
0.7582	Intermediate Similarity	NPC280367
0.7582	Intermediate Similarity	NPC469469
0.7579	Intermediate Similarity	NPC248312
0.7579	Intermediate Similarity	NPC470137
0.7576	Intermediate Similarity	NPC473605
0.7576	Intermediate Similarity	NPC475540
0.7576	Intermediate Similarity	NPC255410
0.7576	Intermediate Similarity	NPC475375
0.7576	Intermediate Similarity	NPC288350
0.7576	Intermediate Similarity	NPC173329
0.7576	Intermediate Similarity	NPC473765
0.7576	Intermediate Similarity	NPC475525
0.7576	Intermediate Similarity	NPC475241
0.7576	Intermediate Similarity	NPC475164
0.7576	Intermediate Similarity	NPC476066
0.7576	Intermediate Similarity	NPC475593
0.7573	Intermediate Similarity	NPC220964
0.7573	Intermediate Similarity	NPC474917
0.7573	Intermediate Similarity	NPC86095
0.7573	Intermediate Similarity	NPC475676
0.757	Intermediate Similarity	NPC48249
0.757	Intermediate Similarity	NPC1046
0.757	Intermediate Similarity	NPC80843
0.7556	Intermediate Similarity	NPC86971
0.7553	Intermediate Similarity	NPC278283
0.7551	Intermediate Similarity	NPC96736
0.7551	Intermediate Similarity	NPC71589
0.7551	Intermediate Similarity	NPC294293
0.7551	Intermediate Similarity	NPC178949
0.7549	Intermediate Similarity	NPC473596
0.7549	Intermediate Similarity	NPC13171
0.7549	Intermediate Similarity	NPC471599
0.7549	Intermediate Similarity	NPC222062
0.7549	Intermediate Similarity	NPC195510
0.7547	Intermediate Similarity	NPC472508
0.7547	Intermediate Similarity	NPC242611
0.7547	Intermediate Similarity	NPC274507
0.7545	Intermediate Similarity	NPC234522
0.7527	Intermediate Similarity	NPC288471
0.7527	Intermediate Similarity	NPC473308
0.7526	Intermediate Similarity	NPC302584
0.7525	Intermediate Similarity	NPC64348
0.7525	Intermediate Similarity	NPC324667
0.7524	Intermediate Similarity	NPC295389
0.7524	Intermediate Similarity	NPC135015
0.7524	Intermediate Similarity	NPC217921
0.7524	Intermediate Similarity	NPC472507
0.7524	Intermediate Similarity	NPC128795
0.7524	Intermediate Similarity	NPC48548

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 NPC472199 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1670
0.2-0.3	3784
0.3-0.4	2280
0.4-0.5	856
0.5-0.6	292
0.6-0.7	88
0.7-0.8	15
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
0.8478	Intermediate Similarity	NPD7983	Approved
0.8172	Intermediate Similarity	NPD46	Approved
0.8172	Intermediate Similarity	NPD6698	Approved
0.7959	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7839	Suspended
0.7692	Intermediate Similarity	NPD6686	Approved
0.7658	Intermediate Similarity	NPD8515	Approved
0.7658	Intermediate Similarity	NPD8513	Phase 3
0.7658	Intermediate Similarity	NPD8516	Approved
0.7658	Intermediate Similarity	NPD8517	Approved
0.7642	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7838	Discovery
0.7345	Intermediate Similarity	NPD8444	Approved
0.7304	Intermediate Similarity	NPD8342	Approved
0.7304	Intermediate Similarity	NPD8340	Approved
0.7304	Intermediate Similarity	NPD8341	Approved
0.7304	Intermediate Similarity	NPD8299	Approved
0.7273	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5778	Approved
0.7217	Intermediate Similarity	NPD7830	Approved
0.7217	Intermediate Similarity	NPD7829	Approved
0.7113	Intermediate Similarity	NPD4250	Approved
0.7113	Intermediate Similarity	NPD4251	Approved
0.7103	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8451	Approved
0.7053	Intermediate Similarity	NPD7154	Phase 3
0.7034	Intermediate Similarity	NPD8448	Approved
0.7034	Intermediate Similarity	NPD8074	Phase 3
0.701	Intermediate Similarity	NPD4249	Approved
0.7	Intermediate Similarity	NPD7637	Suspended
0.6991	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6412	Phase 2
0.693	Remote Similarity	NPD7641	Discontinued
0.6923	Remote Similarity	NPD8328	Phase 3
0.6923	Remote Similarity	NPD7642	Approved
0.6915	Remote Similarity	NPD4820	Approved
0.6915	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD4821	Approved
0.6915	Remote Similarity	NPD4819	Approved
0.6909	Remote Similarity	NPD6371	Approved
0.6882	Remote Similarity	NPD4268	Approved
0.6882	Remote Similarity	NPD4271	Approved
0.686	Remote Similarity	NPD8390	Approved
0.686	Remote Similarity	NPD8391	Approved
0.686	Remote Similarity	NPD8392	Approved
0.6804	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6101	Approved
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5344	Discontinued
0.6777	Remote Similarity	NPD7319	Approved
0.6771	Remote Similarity	NPD4269	Approved
0.6771	Remote Similarity	NPD4270	Approved
0.6762	Remote Similarity	NPD4225	Approved
0.6752	Remote Similarity	NPD8033	Approved
0.6752	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8133	Approved
0.6701	Remote Similarity	NPD5362	Discontinued
0.6695	Remote Similarity	NPD8080	Discontinued
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD8273	Phase 1
0.6667	Remote Similarity	NPD7507	Approved
0.6638	Remote Similarity	NPD7327	Approved
0.6638	Remote Similarity	NPD7328	Approved
0.661	Remote Similarity	NPD8379	Approved
0.661	Remote Similarity	NPD8378	Approved
0.661	Remote Similarity	NPD8335	Approved
0.661	Remote Similarity	NPD8296	Approved
0.661	Remote Similarity	NPD8380	Approved
0.6581	Remote Similarity	NPD7516	Approved
0.6566	Remote Similarity	NPD5363	Approved
0.6562	Remote Similarity	NPD4252	Approved
0.6531	Remote Similarity	NPD6110	Phase 1
0.6531	Remote Similarity	NPD5331	Approved
0.6531	Remote Similarity	NPD5332	Approved
0.6495	Remote Similarity	NPD4790	Discontinued
0.6495	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD7503	Approved
0.646	Remote Similarity	NPD6421	Discontinued
0.6429	Remote Similarity	NPD6435	Approved
0.6408	Remote Similarity	NPD5785	Approved
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6648	Approved
0.6389	Remote Similarity	NPD7639	Approved
0.6389	Remote Similarity	NPD7640	Approved
0.6381	Remote Similarity	NPD5282	Discontinued
0.6354	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8293	Discontinued
0.6328	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5370	Suspended
0.6296	Remote Similarity	NPD7638	Approved
0.629	Remote Similarity	NPD7736	Approved
0.6279	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7524	Approved
0.6273	Remote Similarity	NPD8086	Approved
0.6273	Remote Similarity	NPD8139	Approved
0.6273	Remote Similarity	NPD8085	Approved
0.6273	Remote Similarity	NPD8082	Approved
0.6273	Remote Similarity	NPD8084	Approved
0.6273	Remote Similarity	NPD8083	Approved
0.6273	Remote Similarity	NPD8138	Approved
0.6271	Remote Similarity	NPD7500	Approved
0.6238	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD5368	Approved
0.6216	Remote Similarity	NPD8276	Approved
0.6216	Remote Similarity	NPD8275	Approved
0.6168	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD8081	Approved
0.6154	Remote Similarity	NPD896	Approved
0.6154	Remote Similarity	NPD897	Approved
0.6154	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD898	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7115	Discovery
0.6129	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8415	Approved
0.6106	Remote Similarity	NPD8393	Approved
0.6068	Remote Similarity	NPD6053	Discontinued
0.6066	Remote Similarity	NPD8267	Approved
0.6066	Remote Similarity	NPD8266	Approved
0.6066	Remote Similarity	NPD8269	Approved
0.6066	Remote Similarity	NPD8268	Approved
0.6053	Remote Similarity	NPD8307	Discontinued
0.6053	Remote Similarity	NPD8140	Approved
0.6048	Remote Similarity	NPD7492	Approved
0.6043	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8039	Approved
0.604	Remote Similarity	NPD6695	Phase 3
0.6032	Remote Similarity	NPD8336	Approved
0.6032	Remote Similarity	NPD8337	Approved
0.6023	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6422	Discontinued
0.6	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.5984	Remote Similarity	NPD6059	Approved
0.5984	Remote Similarity	NPD6054	Approved
0.5984	Remote Similarity	NPD6319	Approved
0.5983	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6399	Phase 3
0.5965	Remote Similarity	NPD5048	Discontinued
0.5963	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7750	Discontinued
0.596	Remote Similarity	NPD7329	Approved
0.5952	Remote Similarity	NPD7078	Approved
0.5948	Remote Similarity	NPD8306	Approved
0.5948	Remote Similarity	NPD8305	Approved
0.5948	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD3168	Discontinued
0.5897	Remote Similarity	NPD8087	Discontinued
0.5882	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3669	Approved
0.5868	Remote Similarity	NPD7505	Discontinued
0.5849	Remote Similarity	NPD1695	Approved
0.5846	Remote Similarity	NPD8338	Approved
0.5841	Remote Similarity	NPD7632	Discontinued
0.5833	Remote Similarity	NPD3181	Approved
0.5824	Remote Similarity	NPD7909	Approved
0.5806	Remote Similarity	NPD6015	Approved
0.5806	Remote Similarity	NPD6016	Approved
0.58	Remote Similarity	NPD6929	Approved
0.5798	Remote Similarity	NPD6430	Approved
0.5798	Remote Similarity	NPD8297	Approved
0.5798	Remote Similarity	NPD6882	Approved
0.5798	Remote Similarity	NPD6429	Approved
0.5784	Remote Similarity	NPD5209	Approved
0.578	Remote Similarity	NPD7748	Approved
0.5778	Remote Similarity	NPD368	Approved
0.5776	Remote Similarity	NPD6685	Approved
0.5766	Remote Similarity	NPD7902	Approved
0.5763	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.576	Remote Similarity	NPD5988	Approved
0.5758	Remote Similarity	NPD6925	Approved
0.5758	Remote Similarity	NPD4756	Discovery
0.5758	Remote Similarity	NPD5776	Phase 2
0.5743	Remote Similarity	NPD7332	Phase 2
0.5743	Remote Similarity	NPD6931	Approved
0.5743	Remote Similarity	NPD7514	Phase 3
0.5743	Remote Similarity	NPD6930	Phase 2
0.5738	Remote Similarity	NPD6009	Approved
0.5735	Remote Similarity	NPD8384	Approved
0.5714	Remote Similarity	NPD8264	Approved
0.5714	Remote Similarity	NPD2204	Approved
0.5714	Remote Similarity	NPD6067	Discontinued
0.57	Remote Similarity	NPD3732	Approved
0.57	Remote Similarity	NPD7145	Approved
0.57	Remote Similarity	NPD4238	Approved
0.57	Remote Similarity	NPD4802	Phase 2
0.5692	Remote Similarity	NPD6914	Discontinued
0.5686	Remote Similarity	NPD6902	Approved
0.568	Remote Similarity	NPD6921	Approved

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