NPASS Compound

Structure

CID291154 OpenBabel06191716102D 35 37 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 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 -6.5622 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -2.5981 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 -7.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 -4.3301 -1.5000 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 -5.1962 2.0000 0.0000 C 0 0 0 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 -6.0622 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5622 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 1 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -6.5622 -2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5622 -2.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 2 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 33 1 0 0 0 0 8 34 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 17 22 2 0 0 0 0 17 35 1 0 0 0 0 18 23 1 0 0 0 0 18 25 2 0 0 0 0 19 27 1 1 0 0 0 20 27 1 6 0 0 0 20 28 1 0 0 0 0 21 28 1 1 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 30 2 0 0 0 0 24 31 2 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 25 35 1 0 0 0 0 26 32 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.29
Volume:	515.524
LogP:	3.413
LogD:	3.015
LogS:	-4.279
# Rotatable Bonds:	8
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	4.794
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.604
MDCK Permeability:	1.8003513105213642e-05
Pgp-inhibitor:	0.94
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.133

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.33
Plasma Protein Binding (PPB):	77.14737701416016%
Volume Distribution (VD):	1.479
Pgp-substrate:	19.500009536743164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.105
CYP1A2-substrate:	0.869
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.24
CYP2C9-substrate:	0.263
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	8.579
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.595
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.811
Carcinogencity:	0.918
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC291154

Natural Product ID:	NPC291154
*Common Name:**	Collectotrichin A
IUPAC Name:	methyl 5-[[(1S,4aS,5R,6S,8aS)-6-hydroxy-5-(3-hydroxy-3-methylbutyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-6-methoxy-2-methyl-4-oxopyran-3-carboxylate
Synonyms:
Standard InCHIKey:	IUNGBSYMDFEAMS-KPRONASWSA-N
Standard InCHI:	InChI=1S/C28H42O7/c1-16-9-10-20-27(5,12-11-21(29)28(20,6)14-13-26(3,4)32)19(16)15-18-23(30)22(24(31)33-7)17(2)35-25(18)34-8/h19-21,29,32H,1,9-15H2,2-8H3/t19-,20-,21-,27-,28+/m0/s1
SMILES:	COC(=O)c1c(C)oc(c(c1=O)C[C@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@@H]([C@]2(C)CCC(O)(C)C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456258
PubChem CID:	93332
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6656	Drosophyllum lusitanicum	Species	Drosophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5694	Siphonaria baconi	Species	Chytriomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10481	Coprosma tenuicaulis	Species	Rubiaceae	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	LD50	=	16.0	mg.kg-1	PMID[515430]

☑ 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 NPC291154 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	333
0.1-0.2	1380
0.2-0.3	2894
0.3-0.4	5466
0.4-0.5	10495
0.5-0.6	8869
0.6-0.7	7485
0.7-0.8	5647
0.8-0.85	114
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8351	Intermediate Similarity	NPC50070
0.8333	Intermediate Similarity	NPC471727
0.8208	Intermediate Similarity	NPC475570
0.8155	Intermediate Similarity	NPC117685
0.8155	Intermediate Similarity	NPC54705
0.8137	Intermediate Similarity	NPC253826
0.8131	Intermediate Similarity	NPC473483
0.8113	Intermediate Similarity	NPC266570
0.8113	Intermediate Similarity	NPC34768
0.8095	Intermediate Similarity	NPC95899
0.8077	Intermediate Similarity	NPC471412
0.8058	Intermediate Similarity	NPC316598
0.8056	Intermediate Similarity	NPC476759
0.8039	Intermediate Similarity	NPC242848
0.8039	Intermediate Similarity	NPC134072
0.8039	Intermediate Similarity	NPC234993
0.8037	Intermediate Similarity	NPC179380
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC476769
0.8	Intermediate Similarity	NPC472975
0.8	Intermediate Similarity	NPC476890
0.7982	Intermediate Similarity	NPC478209
0.7981	Intermediate Similarity	NPC471413
0.7981	Intermediate Similarity	NPC474012
0.7981	Intermediate Similarity	NPC476299
0.7981	Intermediate Similarity	NPC476767
0.7963	Intermediate Similarity	NPC90946
0.7963	Intermediate Similarity	NPC300614
0.7944	Intermediate Similarity	NPC478208
0.7944	Intermediate Similarity	NPC189863
0.7944	Intermediate Similarity	NPC127609
0.7925	Intermediate Similarity	NPC471208
0.7925	Intermediate Similarity	NPC478057
0.7925	Intermediate Similarity	NPC476889
0.7925	Intermediate Similarity	NPC120321
0.7921	Intermediate Similarity	NPC139692
0.7921	Intermediate Similarity	NPC199543
0.7909	Intermediate Similarity	NPC324683
0.7905	Intermediate Similarity	NPC93744
0.7905	Intermediate Similarity	NPC476888
0.79	Intermediate Similarity	NPC51486
0.79	Intermediate Similarity	NPC232202
0.789	Intermediate Similarity	NPC31522
0.7885	Intermediate Similarity	NPC108368
0.7885	Intermediate Similarity	NPC57079
0.7879	Intermediate Similarity	NPC104560
0.7876	Intermediate Similarity	NPC474483
0.787	Intermediate Similarity	NPC302788
0.787	Intermediate Similarity	NPC330011
0.787	Intermediate Similarity	NPC329048
0.7864	Intermediate Similarity	NPC98874
0.7864	Intermediate Similarity	NPC202833
0.7857	Intermediate Similarity	NPC110861
0.7857	Intermediate Similarity	NPC472986
0.7857	Intermediate Similarity	NPC73038
0.7857	Intermediate Similarity	NPC322159
0.7857	Intermediate Similarity	NPC472985
0.785	Intermediate Similarity	NPC471937
0.7843	Intermediate Similarity	NPC91010
0.7838	Intermediate Similarity	NPC90952
0.7838	Intermediate Similarity	NPC4573
0.7838	Intermediate Similarity	NPC277769
0.783	Intermediate Similarity	NPC40918
0.783	Intermediate Similarity	NPC471914
0.783	Intermediate Similarity	NPC162973
0.7826	Intermediate Similarity	NPC184555
0.7822	Intermediate Similarity	NPC73457
0.7818	Intermediate Similarity	NPC476766
0.7818	Intermediate Similarity	NPC179642
0.7818	Intermediate Similarity	NPC472666
0.781	Intermediate Similarity	NPC251680
0.7807	Intermediate Similarity	NPC146786
0.7798	Intermediate Similarity	NPC151393
0.7798	Intermediate Similarity	NPC476765
0.7788	Intermediate Similarity	NPC320306
0.7788	Intermediate Similarity	NPC44170
0.7788	Intermediate Similarity	NPC475709
0.7788	Intermediate Similarity	NPC89225
0.7788	Intermediate Similarity	NPC53844
0.7788	Intermediate Similarity	NPC268954
0.7788	Intermediate Similarity	NPC287668
0.7768	Intermediate Similarity	NPC122056
0.7768	Intermediate Similarity	NPC157441
0.7768	Intermediate Similarity	NPC478212
0.7767	Intermediate Similarity	NPC148523
0.7767	Intermediate Similarity	NPC266899
0.7757	Intermediate Similarity	NPC475526
0.7757	Intermediate Similarity	NPC329345
0.7757	Intermediate Similarity	NPC320154
0.7757	Intermediate Similarity	NPC45897
0.7757	Intermediate Similarity	NPC112009
0.7757	Intermediate Similarity	NPC471938
0.7757	Intermediate Similarity	NPC473283
0.7745	Intermediate Similarity	NPC472303
0.7745	Intermediate Similarity	NPC272075
0.7745	Intermediate Similarity	NPC214756
0.7745	Intermediate Similarity	NPC271652
0.7745	Intermediate Similarity	NPC295643
0.7736	Intermediate Similarity	NPC168319
0.7736	Intermediate Similarity	NPC194028
0.7736	Intermediate Similarity	NPC471075
0.7736	Intermediate Similarity	NPC282524
0.7727	Intermediate Similarity	NPC475065
0.7727	Intermediate Similarity	NPC478210
0.7723	Intermediate Similarity	NPC476369
0.7723	Intermediate Similarity	NPC8062
0.7723	Intermediate Similarity	NPC161638
0.7723	Intermediate Similarity	NPC476437
0.7714	Intermediate Similarity	NPC473154
0.7714	Intermediate Similarity	NPC478056
0.7714	Intermediate Similarity	NPC278673
0.7714	Intermediate Similarity	NPC218107
0.7712	Intermediate Similarity	NPC32868
0.7712	Intermediate Similarity	NPC241456
0.7708	Intermediate Similarity	NPC40228
0.7706	Intermediate Similarity	NPC67321
0.7706	Intermediate Similarity	NPC187435
0.7706	Intermediate Similarity	NPC263729
0.77	Intermediate Similarity	NPC143025
0.7699	Intermediate Similarity	NPC147912
0.7699	Intermediate Similarity	NPC67259
0.7692	Intermediate Similarity	NPC240673
0.7692	Intermediate Similarity	NPC167193
0.7692	Intermediate Similarity	NPC7124
0.7692	Intermediate Similarity	NPC471153
0.7692	Intermediate Similarity	NPC472806
0.7692	Intermediate Similarity	NPC17578
0.7692	Intermediate Similarity	NPC29952
0.7685	Intermediate Similarity	NPC476764
0.7685	Intermediate Similarity	NPC476763
0.7685	Intermediate Similarity	NPC222161
0.7679	Intermediate Similarity	NPC12046
0.7679	Intermediate Similarity	NPC194951
0.7677	Intermediate Similarity	NPC477479
0.7677	Intermediate Similarity	NPC477478
0.7672	Intermediate Similarity	NPC476127
0.7672	Intermediate Similarity	NPC476150
0.767	Intermediate Similarity	NPC84893
0.767	Intermediate Similarity	NPC47853
0.767	Intermediate Similarity	NPC105490
0.767	Intermediate Similarity	NPC57117
0.767	Intermediate Similarity	NPC470957
0.767	Intermediate Similarity	NPC470958
0.767	Intermediate Similarity	NPC476415
0.7664	Intermediate Similarity	NPC273005
0.7664	Intermediate Similarity	NPC114540
0.7664	Intermediate Similarity	NPC137430
0.7664	Intermediate Similarity	NPC165250
0.7664	Intermediate Similarity	NPC32577
0.7664	Intermediate Similarity	NPC31058
0.7664	Intermediate Similarity	NPC80781
0.7664	Intermediate Similarity	NPC469606
0.7664	Intermediate Similarity	NPC155332
0.7658	Intermediate Similarity	NPC16270
0.7658	Intermediate Similarity	NPC478211
0.7658	Intermediate Similarity	NPC474567
0.7652	Intermediate Similarity	NPC113448
0.7647	Intermediate Similarity	NPC4036
0.7647	Intermediate Similarity	NPC472814
0.7647	Intermediate Similarity	NPC473944
0.7647	Intermediate Similarity	NPC65120
0.7647	Intermediate Similarity	NPC233455
0.7647	Intermediate Similarity	NPC145067
0.7647	Intermediate Similarity	NPC177037
0.7647	Intermediate Similarity	NPC472978
0.7647	Intermediate Similarity	NPC158030
0.7647	Intermediate Similarity	NPC78594
0.7647	Intermediate Similarity	NPC289479
0.7647	Intermediate Similarity	NPC329842
0.7642	Intermediate Similarity	NPC474718
0.7642	Intermediate Similarity	NPC324841
0.7642	Intermediate Similarity	NPC306856
0.7642	Intermediate Similarity	NPC475156
0.7642	Intermediate Similarity	NPC327431
0.7642	Intermediate Similarity	NPC473576
0.7642	Intermediate Similarity	NPC201406
0.7642	Intermediate Similarity	NPC470074
0.7636	Intermediate Similarity	NPC306265
0.7636	Intermediate Similarity	NPC325054
0.7636	Intermediate Similarity	NPC392
0.7636	Intermediate Similarity	NPC177524
0.7636	Intermediate Similarity	NPC219900
0.7636	Intermediate Similarity	NPC189075
0.7636	Intermediate Similarity	NPC275539
0.7636	Intermediate Similarity	NPC318363
0.7636	Intermediate Similarity	NPC475418
0.7636	Intermediate Similarity	NPC473482
0.7636	Intermediate Similarity	NPC476802
0.7636	Intermediate Similarity	NPC89171
0.7636	Intermediate Similarity	NPC322903
0.7632	Intermediate Similarity	NPC471816
0.7632	Intermediate Similarity	NPC72772
0.7632	Intermediate Similarity	NPC469794
0.7627	Intermediate Similarity	NPC204812
0.7627	Intermediate Similarity	NPC55602
0.7624	Intermediate Similarity	NPC472973
0.7619	Intermediate Similarity	NPC151681
0.7619	Intermediate Similarity	NPC472851
0.7619	Intermediate Similarity	NPC478233
0.7619	Intermediate Similarity	NPC108078

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 NPC291154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	938
0.2-0.3	1812
0.3-0.4	2548
0.4-0.5	2082
0.5-0.6	1047
0.6-0.7	344
0.7-0.8	87
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7885	Intermediate Similarity	NPD7638	Approved
0.781	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD7515	Phase 2
0.7636	Intermediate Similarity	NPD6686	Approved
0.7565	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD7748	Approved
0.7383	Intermediate Similarity	NPD4225	Approved
0.7339	Intermediate Similarity	NPD7632	Discontinued
0.7317	Intermediate Similarity	NPD7319	Approved
0.729	Intermediate Similarity	NPD7902	Approved
0.7257	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6882	Approved
0.7213	Intermediate Similarity	NPD7507	Approved
0.7157	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7131	Intermediate Similarity	NPD7492	Approved
0.7119	Intermediate Similarity	NPD6009	Approved
0.7115	Intermediate Similarity	NPD5328	Approved
0.71	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6054	Approved
0.7083	Intermediate Similarity	NPD6059	Approved
0.7073	Intermediate Similarity	NPD6616	Approved
0.7049	Intermediate Similarity	NPD8328	Phase 3
0.7043	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7503	Approved
0.7018	Intermediate Similarity	NPD6881	Approved
0.7018	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6899	Approved
0.7018	Intermediate Similarity	NPD7320	Approved
0.7016	Intermediate Similarity	NPD7078	Approved
0.7016	Intermediate Similarity	NPD8293	Discontinued
0.7009	Intermediate Similarity	NPD7900	Approved
0.7009	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6079	Approved
0.6972	Remote Similarity	NPD6084	Phase 2
0.6972	Remote Similarity	NPD6083	Phase 2
0.6967	Remote Similarity	NPD6370	Approved
0.696	Remote Similarity	NPD7736	Approved
0.6957	Remote Similarity	NPD6372	Approved
0.6957	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6373	Approved
0.693	Remote Similarity	NPD6412	Phase 2
0.693	Remote Similarity	NPD5697	Approved
0.693	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD6053	Discontinued
0.6917	Remote Similarity	NPD7328	Approved
0.6917	Remote Similarity	NPD7327	Approved
0.6916	Remote Similarity	NPD5778	Approved
0.6916	Remote Similarity	NPD5779	Approved
0.6916	Remote Similarity	NPD4202	Approved
0.6916	Remote Similarity	NPD6399	Phase 3
0.6897	Remote Similarity	NPD6883	Approved
0.6897	Remote Similarity	NPD7102	Approved
0.6897	Remote Similarity	NPD7290	Approved
0.6893	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5785	Approved
0.6885	Remote Similarity	NPD6016	Approved
0.6885	Remote Similarity	NPD6015	Approved
0.687	Remote Similarity	NPD6011	Approved
0.6864	Remote Similarity	NPD8133	Approved
0.6864	Remote Similarity	NPD4632	Approved
0.686	Remote Similarity	NPD7516	Approved
0.6838	Remote Similarity	NPD6869	Approved
0.6838	Remote Similarity	NPD8130	Phase 1
0.6838	Remote Similarity	NPD6847	Approved
0.6838	Remote Similarity	NPD6617	Approved
0.6838	Remote Similarity	NPD6649	Approved
0.6838	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6650	Approved
0.6829	Remote Similarity	NPD5988	Approved
0.6827	Remote Similarity	NPD7334	Approved
0.6827	Remote Similarity	NPD7146	Approved
0.6827	Remote Similarity	NPD6684	Approved
0.6827	Remote Similarity	NPD7521	Approved
0.6827	Remote Similarity	NPD5330	Approved
0.6827	Remote Similarity	NPD6409	Approved
0.6827	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD4755	Approved
0.681	Remote Similarity	NPD6012	Approved
0.681	Remote Similarity	NPD6014	Approved
0.681	Remote Similarity	NPD6013	Approved
0.6803	Remote Similarity	NPD8377	Approved
0.6803	Remote Similarity	NPD8294	Approved
0.6803	Remote Similarity	NPD6319	Approved
0.6796	Remote Similarity	NPD3665	Phase 1
0.6796	Remote Similarity	NPD4786	Approved
0.6796	Remote Similarity	NPD3133	Approved
0.6796	Remote Similarity	NPD3666	Approved
0.6783	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8297	Approved
0.6765	Remote Similarity	NPD3667	Approved
0.6762	Remote Similarity	NPD3573	Approved
0.6752	Remote Similarity	NPD4634	Approved
0.6748	Remote Similarity	NPD8380	Approved
0.6748	Remote Similarity	NPD8335	Approved
0.6748	Remote Similarity	NPD8379	Approved
0.6748	Remote Similarity	NPD8296	Approved
0.6748	Remote Similarity	NPD8033	Approved
0.6748	Remote Similarity	NPD8378	Approved
0.6733	Remote Similarity	NPD4695	Discontinued
0.6731	Remote Similarity	NPD1694	Approved
0.6727	Remote Similarity	NPD5221	Approved
0.6727	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5222	Approved
0.6727	Remote Similarity	NPD4697	Phase 3
0.6726	Remote Similarity	NPD5211	Phase 2
0.6698	Remote Similarity	NPD6903	Approved
0.6698	Remote Similarity	NPD5737	Approved
0.6698	Remote Similarity	NPD6672	Approved
0.6698	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5286	Approved
0.6696	Remote Similarity	NPD5285	Approved
0.6696	Remote Similarity	NPD4700	Approved
0.6696	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD7637	Suspended
0.6637	Remote Similarity	NPD5223	Approved
0.6636	Remote Similarity	NPD4753	Phase 2
0.6636	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD5695	Phase 3
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD6371	Approved
0.6609	Remote Similarity	NPD5141	Approved
0.6607	Remote Similarity	NPD5696	Approved
0.6579	Remote Similarity	NPD5226	Approved
0.6579	Remote Similarity	NPD5225	Approved
0.6579	Remote Similarity	NPD4633	Approved
0.6579	Remote Similarity	NPD5224	Approved
0.6574	Remote Similarity	NPD46	Approved
0.6574	Remote Similarity	NPD6698	Approved
0.6545	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD4788	Approved
0.6535	Remote Similarity	NPD6697	Approved
0.6535	Remote Similarity	NPD6118	Approved
0.6535	Remote Similarity	NPD6115	Approved
0.6535	Remote Similarity	NPD6114	Approved
0.6522	Remote Similarity	NPD5175	Approved
0.6522	Remote Similarity	NPD4754	Approved
0.6522	Remote Similarity	NPD5174	Approved
0.6509	Remote Similarity	NPD4519	Discontinued
0.6509	Remote Similarity	NPD4623	Approved
0.6509	Remote Similarity	NPD5279	Phase 3
0.6508	Remote Similarity	NPD7604	Phase 2
0.6508	Remote Similarity	NPD6067	Discontinued
0.6504	Remote Similarity	NPD6335	Approved
0.6491	Remote Similarity	NPD5344	Discontinued
0.6486	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6904	Approved
0.6481	Remote Similarity	NPD6080	Approved
0.6481	Remote Similarity	NPD6673	Approved
0.648	Remote Similarity	NPD8516	Approved
0.648	Remote Similarity	NPD5983	Phase 2
0.648	Remote Similarity	NPD8515	Approved
0.648	Remote Similarity	NPD8517	Approved
0.6476	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6274	Approved
0.6475	Remote Similarity	NPD6868	Approved
0.646	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7101	Approved
0.6452	Remote Similarity	NPD7100	Approved
0.6442	Remote Similarity	NPD4221	Approved
0.6442	Remote Similarity	NPD4223	Phase 3
0.6423	Remote Similarity	NPD6317	Approved
0.6417	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5363	Approved
0.6415	Remote Similarity	NPD5329	Approved
0.641	Remote Similarity	NPD4767	Approved
0.641	Remote Similarity	NPD4768	Approved
0.6408	Remote Similarity	NPD7525	Registered
0.6406	Remote Similarity	NPD6336	Discontinued
0.6373	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3617	Approved
0.6371	Remote Similarity	NPD6313	Approved
0.6371	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6349	Remote Similarity	NPD6909	Approved
0.6349	Remote Similarity	NPD6921	Approved
0.6349	Remote Similarity	NPD6908	Approved
0.6346	Remote Similarity	NPD5369	Approved
0.6339	Remote Similarity	NPD4629	Approved
0.6339	Remote Similarity	NPD5210	Approved
0.6337	Remote Similarity	NPD6117	Approved
0.633	Remote Similarity	NPD6051	Approved
0.6321	Remote Similarity	NPD4197	Approved
0.6321	Remote Similarity	NPD3668	Phase 3

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