NPASS Compound

Structure

NPC473520 OpenBabel07101718232D 45 48 0 0 1 0 0 0 0 0999 V2000 15.0752 7.4401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0913 7.6187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4447 6.8559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7820 5.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1354 5.1516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4727 4.2103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8261 3.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1635 2.5060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5169 1.7432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6453 2.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5408 1.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5589 3.3784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8542 0.8018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6272 1.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6634 4.3729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2076 0.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5227 0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5769 4.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5449 -0.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3370 4.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9248 3.6919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1916 -2.1777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6370 1.7976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1499 0.9391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3110 -1.7039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0129 0.2447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3860 4.1919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.8983 -1.6652 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9144 -1.4867 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6460 1.9318 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7985 0.0029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3370 2.8828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4896 -0.7199 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2357 -2.6066 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9232 1.2407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8474 -0.3061 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 6.3860 3.1919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4805 -0.5857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 30 1 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 31 1 0 0 0 0 23 26 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 27 29 1 0 0 0 0 27 30 2 0 0 0 0 28 41 1 0 0 0 0 28 42 1 0 0 0 0 29 2 1 6 0 0 0 29 43 1 0 0 0 0 30 38 1 0 0 0 0 31 19 1 6 0 0 0 31 44 1 0 0 0 0 32 39 1 1 0 0 0 33 32 1 1 0 0 0 33 45 1 0 0 0 0 34 24 1 6 0 0 0 34 36 1 0 0 0 0 34 41 1 0 0 0 0 35 25 1 6 0 0 0 35 37 1 0 0 0 0 35 42 1 0 0 0 0 36 22 1 1 0 0 0 36 44 1 0 0 0 0 37 26 1 6 0 0 0 37 45 1 0 0 0 0 38 40 2 0 0 0 0 38 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.48
Volume:	687.837
LogP:	10.372
LogD:	5.478
LogS:	-7.235
# Rotatable Bonds:	22
TPSA:	90.52
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.123
Synthetic Accessibility Score:	4.752
Fsp3:	0.895
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:	-5.043
MDCK Permeability:	1.379233981424477e-05
Pgp-inhibitor:	0.039
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.269

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	98.27686309814453%
Volume Distribution (VD):	0.726
Pgp-substrate:	2.5043044090270996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.066
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.616
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.045

ADMET: Excretion

Clearance (CL):	3.686
Half-life (T1/2):	0.018

ADMET: Toxicity

hERG Blockers:	0.412
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.587
Skin Sensitization:	0.981
Carcinogencity:	0.048
Eye Corrosion:	0.005
Eye Irritation:	0.034
Respiratory Toxicity:	0.137

Download Data

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

Natural Product: NPC473520

Natural Product ID:	NPC473520
*Common Name:**	(2S)-4-[7-[(2R,5S)-5-[(4S,7R)-7-[(2R,5R)-5-[(1R)-1-Hydroxytridecyl]Oxolan-2-Yl]-1,3-Dioxepan-4-Yl]Oxolan-2-Yl]Heptyl]-2-Methyl-2H-Furan-5-One
IUPAC Name:	(2S)-4-[7-[(2R,5S)-5-[(4S,7R)-7-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-1,3-dioxepan-4-yl]oxolan-2-yl]heptyl]-2-methyl-2H-furan-5-one
Synonyms:
Standard InCHIKey:	FJNAHVKQVREHDF-VUODRKSTSA-N
Standard InCHI:	InChI=1S/C38H66O7/c1-3-4-5-6-7-8-9-10-14-17-20-32(39)33-23-26-37(45-33)35-25-24-34(41-28-42-35)36-22-21-31(44-36)19-16-13-11-12-15-18-30-27-29(2)43-38(30)40/h27,29,31-37,39H,3-26,28H2,1-2H3/t29-,31+,32+,33+,34-,35+,36-,37+/m0/s1
SMILES:	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H]1OCO[C@@H](CC1)[C@@H]1CC[C@H](O1)CCCCCCCC1=C[C@@H](OC1=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444465
PubChem CID:	10627838
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[1479382]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791471]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614426]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322367]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917277]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7202	Goniothalamus giganteus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.82	10'-2 ug/ml	PMID[543611]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	4.95	10'-1 ug/ml	PMID[543611]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.83	10'-1 ug/ml	PMID[543611]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	1.62	10'-1 ug/ml	PMID[543611]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	1.32	10'-1 ug/ml	PMID[543611]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	=	2.17	10'-1 ug/ml	PMID[543611]

☑ 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 NPC473520 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	222
0.1-0.2	1777
0.2-0.3	6746
0.3-0.4	15697
0.4-0.5	9952
0.5-0.6	6276
0.6-0.7	1700
0.7-0.8	160
0.8-0.85	96
0.85-0.9	60
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC475173
0.9545	High Similarity	NPC473561
0.9545	High Similarity	NPC473723
0.9545	High Similarity	NPC473663
0.9302	High Similarity	NPC241360
0.9302	High Similarity	NPC132940
0.9302	High Similarity	NPC293136
0.9195	High Similarity	NPC476583
0.9195	High Similarity	NPC20533
0.9195	High Similarity	NPC258068
0.9186	High Similarity	NPC77871
0.9186	High Similarity	NPC39167
0.9186	High Similarity	NPC202055
0.9186	High Similarity	NPC39279
0.9186	High Similarity	NPC9678
0.9186	High Similarity	NPC473671
0.9186	High Similarity	NPC292809
0.9186	High Similarity	NPC319036
0.9186	High Similarity	NPC470400
0.9186	High Similarity	NPC475268
0.9186	High Similarity	NPC235809
0.9186	High Similarity	NPC25764
0.9186	High Similarity	NPC473156
0.9091	High Similarity	NPC169511
0.9091	High Similarity	NPC133730
0.9091	High Similarity	NPC320458
0.9091	High Similarity	NPC473905
0.9091	High Similarity	NPC261952
0.9091	High Similarity	NPC81045
0.9091	High Similarity	NPC287164
0.9091	High Similarity	NPC151403
0.9091	High Similarity	NPC171135
0.9091	High Similarity	NPC242364
0.9091	High Similarity	NPC61257
0.9091	High Similarity	NPC320569
0.9091	High Similarity	NPC172821
0.9091	High Similarity	NPC191929
0.9091	High Similarity	NPC274446
0.9091	High Similarity	NPC39754
0.9091	High Similarity	NPC234077
0.9091	High Similarity	NPC100454
0.908	High Similarity	NPC473840
0.908	High Similarity	NPC282815
0.908	High Similarity	NPC25703
0.908	High Similarity	NPC219652
0.907	High Similarity	NPC156804
0.9	High Similarity	NPC473707
0.8989	High Similarity	NPC473504
0.8989	High Similarity	NPC91067
0.8989	High Similarity	NPC42598
0.8989	High Similarity	NPC93794
0.8989	High Similarity	NPC318963
0.8989	High Similarity	NPC40066
0.8989	High Similarity	NPC81778
0.8989	High Similarity	NPC20621
0.8977	High Similarity	NPC154097
0.8977	High Similarity	NPC473649
0.8977	High Similarity	NPC159750
0.8977	High Similarity	NPC470401
0.8977	High Similarity	NPC473995
0.8966	High Similarity	NPC329615
0.8966	High Similarity	NPC471567
0.8966	High Similarity	NPC120398
0.8966	High Similarity	NPC329838
0.8966	High Similarity	NPC322529
0.8889	High Similarity	NPC473904
0.8889	High Similarity	NPC239517
0.8864	High Similarity	NPC114694
0.8864	High Similarity	NPC171174
0.8864	High Similarity	NPC475581
0.8864	High Similarity	NPC107717
0.8864	High Similarity	NPC231096
0.8864	High Similarity	NPC240695
0.8864	High Similarity	NPC62118
0.8864	High Similarity	NPC142117
0.8864	High Similarity	NPC232555
0.8851	High Similarity	NPC163093
0.8837	High Similarity	NPC473712
0.8837	High Similarity	NPC11332
0.8837	High Similarity	NPC65930
0.8837	High Similarity	NPC94875
0.8837	High Similarity	NPC73310
0.8837	High Similarity	NPC473529
0.8837	High Similarity	NPC180363
0.8837	High Similarity	NPC475159
0.8837	High Similarity	NPC131002
0.8837	High Similarity	NPC329829
0.8837	High Similarity	NPC473780
0.8837	High Similarity	NPC145914
0.8778	High Similarity	NPC139418
0.875	High Similarity	NPC473478
0.875	High Similarity	NPC82795
0.875	High Similarity	NPC231009
0.875	High Similarity	NPC223871
0.875	High Similarity	NPC283085
0.875	High Similarity	NPC473669
0.875	High Similarity	NPC1083
0.875	High Similarity	NPC477014
0.875	High Similarity	NPC132496
0.875	High Similarity	NPC110710
0.875	High Similarity	NPC473651
0.875	High Similarity	NPC66346
0.875	High Similarity	NPC103284
0.875	High Similarity	NPC107986
0.875	High Similarity	NPC477018
0.875	High Similarity	NPC477013
0.875	High Similarity	NPC100921
0.875	High Similarity	NPC286338
0.8736	High Similarity	NPC144415
0.8736	High Similarity	NPC253801
0.8667	High Similarity	NPC280621
0.8667	High Similarity	NPC21208
0.8667	High Similarity	NPC20339
0.8667	High Similarity	NPC40376
0.8667	High Similarity	NPC89001
0.8667	High Similarity	NPC48338
0.8667	High Similarity	NPC233551
0.8652	High Similarity	NPC134885
0.8652	High Similarity	NPC134865
0.8652	High Similarity	NPC477010
0.8652	High Similarity	NPC309211
0.8652	High Similarity	NPC69082
0.8652	High Similarity	NPC473687
0.8652	High Similarity	NPC279267
0.8652	High Similarity	NPC134807
0.8652	High Similarity	NPC477015
0.8652	High Similarity	NPC308412
0.8652	High Similarity	NPC210218
0.8652	High Similarity	NPC219498
0.8652	High Similarity	NPC103523
0.8652	High Similarity	NPC204686
0.8571	High Similarity	NPC477016
0.8571	High Similarity	NPC477011
0.8571	High Similarity	NPC477017
0.8556	High Similarity	NPC178215
0.8495	Intermediate Similarity	NPC11456
0.8444	Intermediate Similarity	NPC112685
0.8444	Intermediate Similarity	NPC47937
0.837	Intermediate Similarity	NPC130359
0.837	Intermediate Similarity	NPC280612
0.837	Intermediate Similarity	NPC14901
0.8352	Intermediate Similarity	NPC477012
0.8333	Intermediate Similarity	NPC182383
0.8022	Intermediate Similarity	NPC288471
0.7879	Intermediate Similarity	NPC187268
0.7826	Intermediate Similarity	NPC41856
0.7732	Intermediate Similarity	NPC81419
0.7732	Intermediate Similarity	NPC179746
0.7732	Intermediate Similarity	NPC320089
0.7717	Intermediate Similarity	NPC229799
0.7717	Intermediate Similarity	NPC284472
0.7717	Intermediate Similarity	NPC286770
0.7708	Intermediate Similarity	NPC475995
0.7708	Intermediate Similarity	NPC474098
0.7708	Intermediate Similarity	NPC118078
0.7677	Intermediate Similarity	NPC306041
0.7647	Intermediate Similarity	NPC86077
0.7629	Intermediate Similarity	NPC208886
0.7629	Intermediate Similarity	NPC12172
0.7629	Intermediate Similarity	NPC30515
0.7609	Intermediate Similarity	NPC474959
0.7609	Intermediate Similarity	NPC310450
0.7609	Intermediate Similarity	NPC475046
0.7609	Intermediate Similarity	NPC11383
0.7579	Intermediate Similarity	NPC248602
0.7551	Intermediate Similarity	NPC238090
0.7551	Intermediate Similarity	NPC472196
0.7551	Intermediate Similarity	NPC472195
0.7526	Intermediate Similarity	NPC473448
0.7526	Intermediate Similarity	NPC474761
0.7526	Intermediate Similarity	NPC473619
0.7526	Intermediate Similarity	NPC80875
0.7526	Intermediate Similarity	NPC476004
0.7526	Intermediate Similarity	NPC51004
0.7525	Intermediate Similarity	NPC472015
0.75	Intermediate Similarity	NPC54731
0.75	Intermediate Similarity	NPC21693
0.75	Intermediate Similarity	NPC474471
0.75	Intermediate Similarity	NPC236649
0.75	Intermediate Similarity	NPC469469
0.75	Intermediate Similarity	NPC474917
0.75	Intermediate Similarity	NPC227379
0.75	Intermediate Similarity	NPC475739
0.75	Intermediate Similarity	NPC153805
0.7475	Intermediate Similarity	NPC159698
0.7475	Intermediate Similarity	NPC474338
0.7474	Intermediate Similarity	NPC475019
0.7474	Intermediate Similarity	NPC474949
0.7471	Intermediate Similarity	NPC84038
0.7453	Intermediate Similarity	NPC219900
0.7453	Intermediate Similarity	NPC177524
0.7453	Intermediate Similarity	NPC475960
0.7453	Intermediate Similarity	NPC392
0.7449	Intermediate Similarity	NPC473321
0.7449	Intermediate Similarity	NPC477349
0.7449	Intermediate Similarity	NPC184463
0.7444	Intermediate Similarity	NPC475711
0.7426	Intermediate Similarity	NPC476612
0.7426	Intermediate Similarity	NPC476613
0.7423	Intermediate Similarity	NPC295312

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 NPC473520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	2529
0.2-0.3	4063
0.3-0.4	1690
0.4-0.5	486
0.5-0.6	152
0.6-0.7	18
0.7-0.8	1
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
0.7453	Intermediate Similarity	NPD6686	Approved
0.7347	Intermediate Similarity	NPD6698	Approved
0.7347	Intermediate Similarity	NPD46	Approved
0.7196	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7838	Discovery
0.6786	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD6371	Approved
0.6475	Remote Similarity	NPD7507	Approved
0.6417	Remote Similarity	NPD8517	Approved
0.6417	Remote Similarity	NPD8513	Phase 3
0.6417	Remote Similarity	NPD8515	Approved
0.6417	Remote Similarity	NPD8516	Approved
0.6415	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4250	Approved
0.6373	Remote Similarity	NPD4251	Approved
0.6337	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7319	Approved
0.6311	Remote Similarity	NPD7829	Approved
0.6311	Remote Similarity	NPD7830	Approved
0.6293	Remote Similarity	NPD6053	Discontinued
0.6292	Remote Similarity	NPD3197	Phase 1
0.6283	Remote Similarity	NPD6412	Phase 2
0.6275	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD1695	Approved
0.6238	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD8294	Approved
0.6198	Remote Similarity	NPD8377	Approved
0.619	Remote Similarity	NPD5785	Approved
0.6176	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7328	Approved
0.6167	Remote Similarity	NPD7327	Approved
0.6148	Remote Similarity	NPD8296	Approved
0.6148	Remote Similarity	NPD8335	Approved
0.6148	Remote Similarity	NPD8379	Approved
0.6148	Remote Similarity	NPD8033	Approved
0.6148	Remote Similarity	NPD8378	Approved
0.6148	Remote Similarity	NPD8380	Approved
0.6139	Remote Similarity	NPD7154	Phase 3
0.6139	Remote Similarity	NPD5362	Discontinued
0.6126	Remote Similarity	NPD5344	Discontinued
0.6116	Remote Similarity	NPD7516	Approved
0.6091	Remote Similarity	NPD7638	Approved
0.6091	Remote Similarity	NPD4225	Approved
0.6055	Remote Similarity	NPD7839	Suspended
0.6048	Remote Similarity	NPD7642	Approved
0.604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7640	Approved
0.6036	Remote Similarity	NPD7639	Approved
0.6034	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7641	Discontinued
0.6032	Remote Similarity	NPD8074	Phase 3
0.602	Remote Similarity	NPD4756	Discovery
0.6019	Remote Similarity	NPD5363	Approved
0.6016	Remote Similarity	NPD8444	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7736	Approved
0.5966	Remote Similarity	NPD8133	Approved
0.5914	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD8293	Discontinued
0.5906	Remote Similarity	NPD7078	Approved
0.5887	Remote Similarity	NPD8266	Approved
0.5887	Remote Similarity	NPD8268	Approved
0.5887	Remote Similarity	NPD8267	Approved
0.5887	Remote Similarity	NPD8269	Approved
0.5887	Remote Similarity	NPD7503	Approved
0.5882	Remote Similarity	NPD6435	Approved
0.5873	Remote Similarity	NPD7492	Approved
0.584	Remote Similarity	NPD6370	Approved
0.5827	Remote Similarity	NPD8451	Approved
0.5827	Remote Similarity	NPD6616	Approved
0.5825	Remote Similarity	NPD6110	Phase 1
0.5816	Remote Similarity	NPD8039	Approved
0.5806	Remote Similarity	NPD6054	Approved
0.58	Remote Similarity	NPD4271	Approved
0.58	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4268	Approved
0.5794	Remote Similarity	NPD8328	Phase 3
0.5784	Remote Similarity	NPD4790	Discontinued
0.5781	Remote Similarity	NPD8448	Approved
0.578	Remote Similarity	NPD5779	Approved
0.578	Remote Similarity	NPD5778	Approved
0.5778	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6648	Approved
0.5741	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4269	Approved
0.5728	Remote Similarity	NPD4270	Approved
0.5728	Remote Similarity	NPD5209	Approved
0.5727	Remote Similarity	NPD5282	Discontinued
0.5714	Remote Similarity	NPD1694	Approved
0.5714	Remote Similarity	NPD8080	Discontinued
0.5714	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7500	Approved
0.5691	Remote Similarity	NPD6009	Approved
0.5691	Remote Similarity	NPD7115	Discovery
0.5686	Remote Similarity	NPD4820	Approved
0.5686	Remote Similarity	NPD4821	Approved
0.5686	Remote Similarity	NPD4819	Approved
0.5686	Remote Similarity	NPD4822	Approved
0.5686	Remote Similarity	NPD5368	Approved
0.5686	Remote Similarity	NPD4252	Approved
0.5682	Remote Similarity	NPD2267	Suspended
0.568	Remote Similarity	NPD6059	Approved
0.5673	Remote Similarity	NPD5331	Approved
0.5673	Remote Similarity	NPD5332	Approved
0.5669	Remote Similarity	NPD6067	Discontinued
0.5667	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5786	Approved
0.5649	Remote Similarity	NPD8392	Approved
0.5649	Remote Similarity	NPD8391	Approved
0.5649	Remote Similarity	NPD8390	Approved
0.5635	Remote Similarity	NPD6015	Approved
0.5635	Remote Similarity	NPD6016	Approved
0.5632	Remote Similarity	NPD3730	Approved
0.5632	Remote Similarity	NPD3196	Approved
0.5632	Remote Similarity	NPD3194	Approved
0.5632	Remote Similarity	NPD3728	Approved
0.5632	Remote Similarity	NPD3195	Phase 2
0.5632	Remote Similarity	NPD4266	Approved
0.5631	Remote Similarity	NPD5369	Approved
0.5625	Remote Similarity	NPD8341	Approved
0.5625	Remote Similarity	NPD8299	Approved
0.5625	Remote Similarity	NPD8340	Approved
0.5625	Remote Similarity	NPD8342	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