NPASS Compound

Structure

CID124626 OpenBabel06191715482D 46 50 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -1.7321 -3.0000 0.0000 C 0 0 0 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 -1.7321 -2.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 1.7321 1.0000 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 -4.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 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 2.5981 2.5000 0.0000 C 0 0 0 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 0.0000 0.0000 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 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 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -3.4641 1.0000 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 45 1 0 0 0 0 2 46 1 0 0 0 0 3 8 1 0 0 0 0 3 21 2 0 0 0 0 4 9 2 0 0 0 0 4 21 1 0 0 0 0 5 10 1 0 0 0 0 5 22 2 0 0 0 0 6 11 2 0 0 0 0 6 22 1 0 0 0 0 7 12 2 0 0 0 0 7 23 1 0 0 0 0 8 25 2 0 0 0 0 9 25 1 0 0 0 0 10 26 2 0 0 0 0 11 26 1 0 0 0 0 12 29 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 37 1 0 0 0 0 16 38 1 0 0 0 0 17 24 1 0 0 0 0 17 28 2 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 19 24 1 0 0 0 0 19 32 2 0 0 0 0 20 27 1 0 0 0 0 20 30 2 0 0 0 0 24 27 2 0 0 0 0 25 39 1 0 0 0 0 26 40 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 28 35 1 0 0 0 0 29 31 2 0 0 0 0 29 41 1 0 0 0 0 30 32 1 0 0 0 0 30 42 1 0 0 0 0 31 45 1 0 0 0 0 32 46 1 0 0 0 0 33 23 1 6 0 0 0 33 34 1 0 0 0 0 34 36 1 1 0 0 0 35 37 1 0 0 0 0 35 43 2 0 0 0 0 36 38 2 3 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.25
Volume:	641.198
LogP:	3.46
LogD:	3.311
LogS:	-4.878
# Rotatable Bonds:	13
TPSA:	160.74
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.093
Synthetic Accessibility Score:	3.412
Fsp3:	0.194
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.055
MDCK Permeability:	5.740292635891819e-06
Pgp-inhibitor:	0.334
Pgp-substrate:	0.718
Human Intestinal Absorption (HIA):	0.918
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	97.86365509033203%
Volume Distribution (VD):	0.7
Pgp-substrate:	0.9842720627784729%

ADMET: Metabolism

CYP1A2-inhibitor:	0.711
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.419
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.483
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.47
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.394

ADMET: Excretion

Clearance (CL):	7.396
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.787
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.419
AMES Toxicity:	0.791
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.933
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.059

Download Data

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

Natural Product: NPC124626

Natural Product ID:	NPC124626
*Common Name:**	Cannabisin D
IUPAC Name:	(1R,2S)-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-N,3-N-bis[2-(4-hydroxyphenyl)ethyl]-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxamide
Synonyms:	Cannabisin D
Standard InCHIKey:	XYTYRVFKBJENPE-KKLWWLSJSA-N
Standard InCHI:	InChI=1S/C36H36N2O8/c1-45-31-18-23(7-12-29(31)41)33-27-20-30(42)32(46-2)19-24(27)17-28(35(43)37-15-13-21-3-8-25(39)9-4-21)34(33)36(44)38-16-14-22-5-10-26(40)11-6-22/h3-12,17-20,33-34,39-42H,13-16H2,1-2H3,(H,37,43)(H,38,44)/t33-,34-/m1/s1
SMILES:	COc1cc2C=C(C(=O)NCCc3ccc(cc3)O)[C@H]([C@@H](c2cc1O)c1ccc(c(c1)OC)O)C(=NCCc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445592
PubChem CID:	44584134
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans

*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
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11858758]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	81000.0	nM	PMID[456151]

☑ 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 NPC124626 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	242
0.1-0.2	1276
0.2-0.3	5066
0.3-0.4	12377
0.4-0.5	4854
0.5-0.6	11948
0.6-0.7	6547
0.7-0.8	381
0.8-0.85	2
0.85-0.9	0
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9435	High Similarity	NPC469689
0.9435	High Similarity	NPC471031
0.9266	High Similarity	NPC281629
0.7989	Intermediate Similarity	NPC138083
0.7869	Intermediate Similarity	NPC32064
0.7824	Intermediate Similarity	NPC5462
0.7802	Intermediate Similarity	NPC108434
0.7802	Intermediate Similarity	NPC475215
0.7751	Intermediate Similarity	NPC100478
0.7751	Intermediate Similarity	NPC222039
0.7727	Intermediate Similarity	NPC107602
0.7701	Intermediate Similarity	NPC478189
0.7663	Intermediate Similarity	NPC256935
0.766	Intermediate Similarity	NPC276120
0.765	Intermediate Similarity	NPC164608
0.7632	Intermediate Similarity	NPC64140
0.7632	Intermediate Similarity	NPC174122
0.7602	Intermediate Similarity	NPC472410
0.7579	Intermediate Similarity	NPC234069
0.7557	Intermediate Similarity	NPC52475
0.7557	Intermediate Similarity	NPC127402
0.7544	Intermediate Similarity	NPC78987
0.7544	Intermediate Similarity	NPC82336
0.7539	Intermediate Similarity	NPC29531
0.7527	Intermediate Similarity	NPC121275
0.7527	Intermediate Similarity	NPC284183
0.7527	Intermediate Similarity	NPC4138
0.7514	Intermediate Similarity	NPC18614
0.7487	Intermediate Similarity	NPC279665
0.7486	Intermediate Similarity	NPC42549
0.7486	Intermediate Similarity	NPC256012
0.7486	Intermediate Similarity	NPC268503
0.7486	Intermediate Similarity	NPC250846
0.7486	Intermediate Similarity	NPC90984
0.7486	Intermediate Similarity	NPC240841
0.7486	Intermediate Similarity	NPC317272
0.7486	Intermediate Similarity	NPC153644
0.7476	Intermediate Similarity	NPC82056
0.7471	Intermediate Similarity	NPC231572
0.7459	Intermediate Similarity	NPC158900
0.7459	Intermediate Similarity	NPC135006
0.7458	Intermediate Similarity	NPC76213
0.7458	Intermediate Similarity	NPC277669
0.7457	Intermediate Similarity	NPC169214
0.7457	Intermediate Similarity	NPC192597
0.7457	Intermediate Similarity	NPC229218
0.7457	Intermediate Similarity	NPC141817
0.7457	Intermediate Similarity	NPC176030
0.7416	Intermediate Similarity	NPC475454
0.7416	Intermediate Similarity	NPC118033
0.7416	Intermediate Similarity	NPC473680
0.7416	Intermediate Similarity	NPC475311
0.7416	Intermediate Similarity	NPC275027
0.7416	Intermediate Similarity	NPC473579
0.7405	Intermediate Similarity	NPC66573
0.7405	Intermediate Similarity	NPC473748
0.7391	Intermediate Similarity	NPC476573
0.7391	Intermediate Similarity	NPC149389
0.7391	Intermediate Similarity	NPC35627
0.7391	Intermediate Similarity	NPC81247
0.7377	Intermediate Similarity	NPC475393
0.7374	Intermediate Similarity	NPC473773
0.7374	Intermediate Similarity	NPC477564
0.7374	Intermediate Similarity	NPC2295
0.7374	Intermediate Similarity	NPC475579
0.7368	Intermediate Similarity	NPC298339
0.7366	Intermediate Similarity	NPC109925
0.7365	Intermediate Similarity	NPC114102
0.7345	Intermediate Similarity	NPC60538
0.7345	Intermediate Similarity	NPC207824
0.732	Intermediate Similarity	NPC82457
0.732	Intermediate Similarity	NPC274661
0.732	Intermediate Similarity	NPC11296
0.732	Intermediate Similarity	NPC175890
0.732	Intermediate Similarity	NPC48490
0.73	Intermediate Similarity	NPC244191
0.7296	Intermediate Similarity	NPC471563
0.7295	Intermediate Similarity	NPC38964
0.7287	Intermediate Similarity	NPC477020
0.7287	Intermediate Similarity	NPC66341
0.7287	Intermediate Similarity	NPC192135
0.7286	Intermediate Similarity	NPC242728
0.7283	Intermediate Similarity	NPC106055
0.7283	Intermediate Similarity	NPC110699
0.7282	Intermediate Similarity	NPC191132
0.7282	Intermediate Similarity	NPC41122
0.7282	Intermediate Similarity	NPC60295
0.7282	Intermediate Similarity	NPC318805
0.7273	Intermediate Similarity	NPC26240
0.7273	Intermediate Similarity	NPC91694
0.7273	Intermediate Similarity	NPC50548
0.7273	Intermediate Similarity	NPC69712
0.7273	Intermediate Similarity	NPC300603
0.7273	Intermediate Similarity	NPC477562
0.7268	Intermediate Similarity	NPC226428
0.7243	Intermediate Similarity	NPC3375
0.7243	Intermediate Similarity	NPC255607
0.7241	Intermediate Similarity	NPC138438
0.7241	Intermediate Similarity	NPC908
0.7241	Intermediate Similarity	NPC29599
0.7238	Intermediate Similarity	NPC287757
0.7238	Intermediate Similarity	NPC319320
0.7238	Intermediate Similarity	NPC105942
0.7238	Intermediate Similarity	NPC205392
0.7235	Intermediate Similarity	NPC218530
0.7228	Intermediate Similarity	NPC179250
0.7228	Intermediate Similarity	NPC50380
0.7228	Intermediate Similarity	NPC60186
0.7222	Intermediate Similarity	NPC58661
0.7222	Intermediate Similarity	NPC234318
0.7222	Intermediate Similarity	NPC144314
0.7222	Intermediate Similarity	NPC58310
0.7222	Intermediate Similarity	NPC295977
0.7222	Intermediate Similarity	NPC24228
0.7219	Intermediate Similarity	NPC214869
0.7202	Intermediate Similarity	NPC195749
0.7202	Intermediate Similarity	NPC52029
0.7202	Intermediate Similarity	NPC35961
0.7191	Intermediate Similarity	NPC24233
0.7191	Intermediate Similarity	NPC428
0.7191	Intermediate Similarity	NPC39361
0.7191	Intermediate Similarity	NPC147390
0.7191	Intermediate Similarity	NPC135538
0.7191	Intermediate Similarity	NPC246587
0.7191	Intermediate Similarity	NPC476571
0.7189	Intermediate Similarity	NPC141574
0.7189	Intermediate Similarity	NPC328649
0.7182	Intermediate Similarity	NPC306011
0.7182	Intermediate Similarity	NPC472838
0.7181	Intermediate Similarity	NPC476751
0.7179	Intermediate Similarity	NPC283207
0.7178	Intermediate Similarity	NPC473460
0.7176	Intermediate Similarity	NPC313737
0.7176	Intermediate Similarity	NPC6854
0.7176	Intermediate Similarity	NPC285078
0.7175	Intermediate Similarity	NPC53520
0.7175	Intermediate Similarity	NPC307205
0.7173	Intermediate Similarity	NPC73555
0.7172	Intermediate Similarity	NPC149962
0.7167	Intermediate Similarity	NPC237441
0.7167	Intermediate Similarity	NPC261322
0.7158	Intermediate Similarity	NPC329969
0.7157	Intermediate Similarity	NPC476565
0.715	Intermediate Similarity	NPC267414
0.715	Intermediate Similarity	NPC30779
0.7143	Intermediate Similarity	NPC473544
0.7143	Intermediate Similarity	NPC80129
0.7143	Intermediate Similarity	NPC187022
0.7143	Intermediate Similarity	NPC475162
0.7143	Intermediate Similarity	NPC475595
0.7143	Intermediate Similarity	NPC475145
0.7143	Intermediate Similarity	NPC266084
0.7143	Intermediate Similarity	NPC155838
0.7143	Intermediate Similarity	NPC475216
0.7143	Intermediate Similarity	NPC83663
0.7135	Intermediate Similarity	NPC474507
0.7135	Intermediate Similarity	NPC191376
0.7135	Intermediate Similarity	NPC179825
0.7135	Intermediate Similarity	NPC321505
0.7135	Intermediate Similarity	NPC473630
0.7135	Intermediate Similarity	NPC327410
0.7127	Intermediate Similarity	NPC26601
0.7121	Intermediate Similarity	NPC85381
0.7121	Intermediate Similarity	NPC256124
0.712	Intermediate Similarity	NPC222524
0.712	Intermediate Similarity	NPC279605
0.7119	Intermediate Similarity	NPC224884
0.7119	Intermediate Similarity	NPC209085
0.7118	Intermediate Similarity	NPC93882
0.7118	Intermediate Similarity	NPC130595
0.7114	Intermediate Similarity	NPC475654
0.7111	Intermediate Similarity	NPC88249
0.7111	Intermediate Similarity	NPC97221
0.7111	Intermediate Similarity	NPC151895
0.7111	Intermediate Similarity	NPC220858
0.7111	Intermediate Similarity	NPC192768
0.711	Intermediate Similarity	NPC471316
0.7107	Intermediate Similarity	NPC259350
0.7107	Intermediate Similarity	NPC223236
0.7104	Intermediate Similarity	NPC305710
0.7104	Intermediate Similarity	NPC25084
0.7104	Intermediate Similarity	NPC186063
0.7104	Intermediate Similarity	NPC247639
0.7101	Intermediate Similarity	NPC304622
0.71	Intermediate Similarity	NPC293624
0.7098	Intermediate Similarity	NPC286119
0.7095	Intermediate Similarity	NPC470019
0.7088	Intermediate Similarity	NPC56635
0.7088	Intermediate Similarity	NPC144283
0.7086	Intermediate Similarity	NPC323204
0.7083	Intermediate Similarity	NPC151167
0.7083	Intermediate Similarity	NPC123722
0.7083	Intermediate Similarity	NPC186898
0.7083	Intermediate Similarity	NPC251571
0.7083	Intermediate Similarity	NPC123228
0.7083	Intermediate Similarity	NPC276466
0.7083	Intermediate Similarity	NPC5018
0.7083	Intermediate Similarity	NPC121400
0.7081	Intermediate Similarity	NPC166014
0.7081	Intermediate Similarity	NPC27410

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 NPC124626 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	598
0.2-0.3	966
0.3-0.4	1770
0.4-0.5	2730
0.5-0.6	2058
0.6-0.7	815
0.7-0.8	55
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
0.7635	Intermediate Similarity	NPD8149	Discontinued
0.7606	Intermediate Similarity	NPD6618	Phase 2
0.7541	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7827	Phase 1
0.7487	Intermediate Similarity	NPD6297	Approved
0.7448	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6851	Approved
0.7421	Intermediate Similarity	NPD6853	Approved
0.7409	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7291	Discontinued
0.7396	Intermediate Similarity	NPD7693	Approved
0.7374	Intermediate Similarity	NPD7110	Phase 1
0.7374	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD824	Approved
0.7345	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6875	Approved
0.7318	Intermediate Similarity	NPD6876	Approved
0.7277	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7833	Phase 2
0.7268	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7831	Phase 2
0.7259	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7177	Discontinued
0.7225	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6873	Phase 2
0.7173	Intermediate Similarity	NPD7038	Approved
0.7173	Intermediate Similarity	NPD7039	Approved
0.7158	Intermediate Similarity	NPD5977	Approved
0.7158	Intermediate Similarity	NPD5978	Approved
0.715	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7298	Approved
0.7128	Intermediate Similarity	NPD6894	Phase 1
0.7121	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2674	Phase 3
0.7116	Intermediate Similarity	NPD8059	Phase 3
0.7116	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7608	Discontinued
0.7102	Intermediate Similarity	NPD8166	Discontinued
0.7062	Intermediate Similarity	NPD8054	Approved
0.7062	Intermediate Similarity	NPD8053	Approved
0.7059	Intermediate Similarity	NPD3145	Approved
0.7059	Intermediate Similarity	NPD3144	Approved
0.7049	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5722	Discontinued
0.7045	Intermediate Similarity	NPD3060	Approved
0.7037	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7801	Approved
0.6995	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7153	Discontinued
0.6983	Remote Similarity	NPD4357	Discontinued
0.698	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7248	Discontinued
0.6952	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2898	Approved
0.6947	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4166	Phase 2
0.693	Remote Similarity	NPD6997	Phase 2
0.6927	Remote Similarity	NPD3845	Phase 1
0.6923	Remote Similarity	NPD7281	Phase 3
0.6923	Remote Similarity	NPD7280	Phase 3
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6834	Approved
0.691	Remote Similarity	NPD6331	Phase 2
0.6902	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6385	Approved
0.6902	Remote Similarity	NPD6386	Approved
0.6902	Remote Similarity	NPD6677	Suspended
0.6898	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4083	Discontinued
0.6893	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7047	Phase 3
0.6885	Remote Similarity	NPD3455	Phase 2
0.6884	Remote Similarity	NPD2488	Approved
0.6884	Remote Similarity	NPD2490	Approved
0.6878	Remote Similarity	NPD6823	Phase 2
0.6875	Remote Similarity	NPD7450	Phase 2
0.6872	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3641	Approved
0.6868	Remote Similarity	NPD7131	Phase 3
0.6868	Remote Similarity	NPD6031	Approved
0.6868	Remote Similarity	NPD6030	Approved
0.6868	Remote Similarity	NPD3640	Phase 3
0.6868	Remote Similarity	NPD3639	Approved
0.6866	Remote Similarity	NPD7669	Phase 3
0.686	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4162	Approved
0.6845	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD42	Phase 2
0.6839	Remote Similarity	NPD6042	Phase 2
0.6839	Remote Similarity	NPD5313	Approved
0.6839	Remote Similarity	NPD5312	Approved
0.6834	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4666	Phase 3
0.6821	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6181	Discontinued
0.6814	Remote Similarity	NPD7565	Approved
0.6813	Remote Similarity	NPD7526	Approved
0.6813	Remote Similarity	NPD52	Approved
0.6813	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7438	Suspended
0.6806	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD5310	Approved
0.6805	Remote Similarity	NPD5311	Approved
0.6804	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7479	Phase 2
0.68	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7037	Approved
0.6793	Remote Similarity	NPD2651	Approved
0.6793	Remote Similarity	NPD2649	Approved
0.6789	Remote Similarity	NPD6107	Approved
0.6788	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6620	Discovery
0.678	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5241	Discontinued
0.6776	Remote Similarity	NPD7427	Discontinued
0.6774	Remote Similarity	NPD8019	Approved
0.6774	Remote Similarity	NPD7577	Discontinued
0.6772	Remote Similarity	NPD6315	Phase 2
0.6772	Remote Similarity	NPD5709	Phase 3
0.6771	Remote Similarity	NPD2489	Approved
0.6771	Remote Similarity	NPD27	Approved
0.6761	Remote Similarity	NPD6895	Approved
0.6761	Remote Similarity	NPD6896	Approved
0.6758	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7773	Phase 2
0.6754	Remote Similarity	NPD6747	Phase 1
0.6746	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1669	Approved
0.6745	Remote Similarity	NPD7225	Discontinued
0.674	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2978	Approved
0.6738	Remote Similarity	NPD2977	Approved
0.6731	Remote Similarity	NPD4040	Phase 1
0.6726	Remote Similarity	NPD7922	Phase 1
0.6726	Remote Similarity	NPD6723	Discontinued
0.6721	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7668	Phase 2
0.6705	Remote Similarity	NPD2653	Approved
0.6703	Remote Similarity	NPD6087	Phase 1
0.6702	Remote Similarity	NPD8127	Discontinued
0.6702	Remote Similarity	NPD7484	Phase 3
0.6702	Remote Similarity	NPD7485	Phase 3
0.6702	Remote Similarity	NPD5967	Approved
0.6701	Remote Similarity	NPD5026	Approved
0.6701	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5028	Approved
0.6701	Remote Similarity	NPD4955	Approved
0.6701	Remote Similarity	NPD4954	Approved
0.6701	Remote Similarity	NPD8251	Approved
0.6701	Remote Similarity	NPD5034	Approved
0.6701	Remote Similarity	NPD8099	Discontinued
0.6701	Remote Similarity	NPD36	Approved
0.6701	Remote Similarity	NPD8252	Approved
0.67	Remote Similarity	NPD7906	Approved
0.6699	Remote Similarity	NPD6612	Phase 2
0.6685	Remote Similarity	NPD8131	Suspended
0.6685	Remote Similarity	NPD4727	Phase 1
0.6685	Remote Similarity	NPD2161	Phase 2
0.6683	Remote Similarity	NPD5071	Phase 2
0.6681	Remote Similarity	NPD8091	Phase 3
0.6667	Remote Similarity	NPD6502	Phase 2
0.6667	Remote Similarity	NPD3053	Approved
0.6667	Remote Similarity	NPD5035	Approved
0.6667	Remote Similarity	NPD7311	Approved
0.6667	Remote Similarity	NPD3055	Approved
0.6667	Remote Similarity	NPD8156	Discontinued
0.6667	Remote Similarity	NPD4584	Approved
0.6667	Remote Similarity	NPD3452	Approved
0.6667	Remote Similarity	NPD7546	Discontinued
0.6667	Remote Similarity	NPD7313	Approved
0.6667	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3450	Approved
0.6667	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5718	Phase 2
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD7312	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7310	Approved
0.6651	Remote Similarity	NPD4583	Approved
0.6651	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4582	Approved
0.665	Remote Similarity	NPD5030	Phase 2
0.665	Remote Similarity	NPD7810	Phase 3
0.665	Remote Similarity	NPD4466	Phase 1

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