NPASS Compound

Structure

NPC473791 OpenBabel07101718322D 46 49 0 0 1 0 0 0 0 0999 V2000 13.3140 5.3697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3301 5.5483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6835 4.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0208 3.8441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3742 3.0813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7115 2.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0649 1.3770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4022 0.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7556 -0.3272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0930 -1.2686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7976 1.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9022 2.3025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8841 0.9013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4464 -2.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8157 2.7093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7837 -2.9728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5758 2.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1636 1.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4304 -4.2481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8758 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3887 -1.1313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5498 -3.7742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2517 -1.8256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.6247 2.1215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1371 -3.7356 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1532 -3.5571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8848 -0.1386 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0373 -2.0675 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5758 0.8125 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7283 -2.7903 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 0.6636 -3.3147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4744 -4.6770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1620 -0.8297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0862 -2.3765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6247 1.1215 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 8.7193 -2.6561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 28 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 11 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 14 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 18 32 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 21 24 1 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 26 29 1 0 0 0 0 26 31 1 0 0 0 0 27 42 1 0 0 0 0 27 43 1 0 0 0 0 28 39 2 0 0 0 0 29 38 1 0 0 0 0 30 16 1 6 0 0 0 30 44 1 0 0 0 0 31 17 1 6 0 0 0 31 45 1 0 0 0 0 32 40 1 1 0 0 0 33 32 1 1 0 0 0 33 46 1 0 0 0 0 34 22 1 6 0 0 0 34 36 1 0 0 0 0 34 42 1 0 0 0 0 35 23 1 6 0 0 0 35 37 1 0 0 0 0 35 43 1 0 0 0 0 36 20 1 1 0 0 0 36 44 1 0 0 0 0 37 24 1 6 0 0 0 37 46 1 0 0 0 0 38 41 2 0 0 0 0 38 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	650.48
Volume:	696.627
LogP:	8.499
LogD:	4.947
LogS:	-7.181
# Rotatable Bonds:	22
TPSA:	100.52
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.093
Synthetic Accessibility Score:	4.974
Fsp3:	0.947
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:	-4.923
MDCK Permeability:	7.632336746610235e-06
Pgp-inhibitor:	0.264
Pgp-substrate:	0.161
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	97.75516510009766%
Volume Distribution (VD):	0.724
Pgp-substrate:	2.2514548301696777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.451
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.072
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.272
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	3.225
Half-life (T1/2):	0.02

ADMET: Toxicity

hERG Blockers:	0.886
Human Hepatotoxicity (H-HT):	0.879
Drug-inuced Liver Injury (DILI):	0.909
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.83
Skin Sensitization:	0.987
Carcinogencity:	0.07
Eye Corrosion:	0.026
Eye Irritation:	0.245
Respiratory Toxicity:	0.749

Download Data

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

Natural Product: NPC473791

Natural Product ID:	NPC473791
*Common Name:**	(5R)-5-[5-[(2R,5S)-5-[(4S,7R)-7-[(2R,5R)-5-[(1R)-1-Hydroxytridecyl]Oxolan-2-Yl]-1,3-Dioxepan-4-Yl]Oxolan-2-Yl]Pentyl]-3-(2-Oxopropyl)Oxolan-2-One
IUPAC Name:	(5R)-5-[5-[(2R,5S)-5-[(4S,7R)-7-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-1,3-dioxepan-4-yl]oxolan-2-yl]pentyl]-3-(2-oxopropyl)oxolan-2-one
Synonyms:
Standard InCHIKey:	IDBFNVNFHAFMAX-SREJVNAZSA-N
Standard InCHI:	InChI=1S/C38H66O8/c1-3-4-5-6-7-8-9-10-11-15-18-32(40)33-21-24-37(46-33)35-23-22-34(42-27-43-35)36-20-19-30(44-36)16-13-12-14-17-31-26-29(25-28(2)39)38(41)45-31/h29-37,40H,3-27H2,1-2H3/t29?,30-,31-,32-,33-,34+,35-,36+,37-/m1/s1
SMILES:	CCCCCCCCCCCCC(C1CCC(O1)C2CCC(OCO2)C3CCC(O3)CCCCCC4CC(C(=O)O4)CC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451951
PubChem CID:	10580116
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

*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	=	2.52	10'-1 ug/ml	PMID[481552]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[481552]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[481552]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	2.71	10'-1 ug/ml	PMID[481552]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	3.06	10'-3 ug/ml	PMID[481552]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	>	1.0	ug ml-1	PMID[481552]

☑ 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 NPC473791 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	634
0.1-0.2	4802
0.2-0.3	13516
0.3-0.4	12310
0.4-0.5	8010
0.5-0.6	2989
0.6-0.7	384
0.7-0.8	30
0.8-0.85	15
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC475616
0.859	High Similarity	NPC475260
0.859	High Similarity	NPC475232
0.859	High Similarity	NPC51249
0.859	High Similarity	NPC473775
0.859	High Similarity	NPC473699
0.859	High Similarity	NPC474100
0.8276	Intermediate Similarity	NPC314364
0.8148	Intermediate Similarity	NPC228411
0.7865	Intermediate Similarity	NPC51662
0.7789	Intermediate Similarity	NPC274695
0.7683	Intermediate Similarity	NPC308096
0.7683	Intermediate Similarity	NPC291228
0.7582	Intermediate Similarity	NPC470009
0.7561	Intermediate Similarity	NPC185419
0.7561	Intermediate Similarity	NPC184550
0.75	Intermediate Similarity	NPC469441
0.75	Intermediate Similarity	NPC228311
0.75	Intermediate Similarity	NPC41674
0.75	Intermediate Similarity	NPC286842
0.7444	Intermediate Similarity	NPC475206
0.7426	Intermediate Similarity	NPC176756
0.7426	Intermediate Similarity	NPC469788
0.7426	Intermediate Similarity	NPC290247
0.7426	Intermediate Similarity	NPC469787
0.7407	Intermediate Similarity	NPC82315
0.7353	Intermediate Similarity	NPC329876
0.7353	Intermediate Similarity	NPC167044
0.7327	Intermediate Similarity	NPC168890
0.732	Intermediate Similarity	NPC328180
0.732	Intermediate Similarity	NPC278028
0.7317	Intermediate Similarity	NPC28526
0.7282	Intermediate Similarity	NPC217041
0.7216	Intermediate Similarity	NPC475785
0.7216	Intermediate Similarity	NPC475765
0.7212	Intermediate Similarity	NPC182185
0.72	Intermediate Similarity	NPC292803
0.7184	Intermediate Similarity	NPC220773
0.7184	Intermediate Similarity	NPC278693
0.7176	Intermediate Similarity	NPC125164
0.7176	Intermediate Similarity	NPC215030
0.7176	Intermediate Similarity	NPC138273
0.7174	Intermediate Similarity	NPC476717
0.7174	Intermediate Similarity	NPC470657
0.7128	Intermediate Similarity	NPC92974
0.7126	Intermediate Similarity	NPC474003
0.71	Intermediate Similarity	NPC478181
0.7097	Intermediate Similarity	NPC31349
0.7075	Intermediate Similarity	NPC98870
0.7073	Intermediate Similarity	NPC206601
0.7073	Intermediate Similarity	NPC469925
0.7065	Intermediate Similarity	NPC478111
0.7065	Intermediate Similarity	NPC476715
0.7059	Intermediate Similarity	NPC114365
0.7059	Intermediate Similarity	NPC18433
0.7059	Intermediate Similarity	NPC132304
0.7059	Intermediate Similarity	NPC123070
0.7059	Intermediate Similarity	NPC88890
0.7059	Intermediate Similarity	NPC154962
0.7059	Intermediate Similarity	NPC169089
0.7059	Intermediate Similarity	NPC177518
0.7059	Intermediate Similarity	NPC18044
0.7045	Intermediate Similarity	NPC470014
0.7021	Intermediate Similarity	NPC58219
0.7021	Intermediate Similarity	NPC177629
0.699	Remote Similarity	NPC306776
0.699	Remote Similarity	NPC166079
0.6989	Remote Similarity	NPC476015
0.6989	Remote Similarity	NPC475019
0.6989	Remote Similarity	NPC474949
0.6989	Remote Similarity	NPC474762
0.6979	Remote Similarity	NPC469627
0.6979	Remote Similarity	NPC475878
0.697	Remote Similarity	NPC263674
0.697	Remote Similarity	NPC58267
0.697	Remote Similarity	NPC261372
0.6966	Remote Similarity	NPC294748
0.6966	Remote Similarity	NPC22742
0.6966	Remote Similarity	NPC158302
0.6966	Remote Similarity	NPC146992
0.6966	Remote Similarity	NPC477346
0.6966	Remote Similarity	NPC477344
0.6966	Remote Similarity	NPC85759
0.6957	Remote Similarity	NPC3464
0.6957	Remote Similarity	NPC475963
0.6957	Remote Similarity	NPC151176
0.6932	Remote Similarity	NPC70996
0.6931	Remote Similarity	NPC162024
0.6931	Remote Similarity	NPC67296
0.6915	Remote Similarity	NPC186148
0.6905	Remote Similarity	NPC211428
0.6905	Remote Similarity	NPC241265
0.6905	Remote Similarity	NPC285003
0.69	Remote Similarity	NPC211087
0.6897	Remote Similarity	NPC217725
0.6893	Remote Similarity	NPC100078
0.6882	Remote Similarity	NPC329749
0.6875	Remote Similarity	NPC65359
0.6869	Remote Similarity	NPC474297
0.6863	Remote Similarity	NPC244969
0.6863	Remote Similarity	NPC213528
0.686	Remote Similarity	NPC206823
0.6835	Remote Similarity	NPC470363
0.6813	Remote Similarity	NPC89843
0.6813	Remote Similarity	NPC477318
0.6813	Remote Similarity	NPC477317
0.6813	Remote Similarity	NPC44782
0.6813	Remote Similarity	NPC186992
0.6813	Remote Similarity	NPC477347
0.6813	Remote Similarity	NPC475667
0.6813	Remote Similarity	NPC27289
0.6813	Remote Similarity	NPC472202
0.6813	Remote Similarity	NPC269318
0.6813	Remote Similarity	NPC259294
0.6813	Remote Similarity	NPC115013
0.6813	Remote Similarity	NPC290012
0.6813	Remote Similarity	NPC123204
0.6813	Remote Similarity	NPC297768
0.6813	Remote Similarity	NPC184915
0.6813	Remote Similarity	NPC238056
0.6813	Remote Similarity	NPC476087
0.6813	Remote Similarity	NPC472203
0.6813	Remote Similarity	NPC119583
0.6813	Remote Similarity	NPC477331
0.6813	Remote Similarity	NPC173328
0.6813	Remote Similarity	NPC307400
0.6813	Remote Similarity	NPC224953
0.6813	Remote Similarity	NPC143421
0.6813	Remote Similarity	NPC472201
0.6813	Remote Similarity	NPC183888
0.6813	Remote Similarity	NPC475270
0.6813	Remote Similarity	NPC472205
0.6813	Remote Similarity	NPC472200
0.6813	Remote Similarity	NPC477319
0.6813	Remote Similarity	NPC475327
0.6813	Remote Similarity	NPC169345
0.6813	Remote Similarity	NPC126685
0.6813	Remote Similarity	NPC472204
0.68	Remote Similarity	NPC304445
0.68	Remote Similarity	NPC476612
0.68	Remote Similarity	NPC476613
0.68	Remote Similarity	NPC236580
0.6796	Remote Similarity	NPC469350
0.6789	Remote Similarity	NPC475537
0.6789	Remote Similarity	NPC308858
0.6786	Remote Similarity	NPC50228
0.6786	Remote Similarity	NPC97736
0.6771	Remote Similarity	NPC474951
0.6771	Remote Similarity	NPC173926
0.6742	Remote Similarity	NPC216883
0.6742	Remote Similarity	NPC476783
0.6742	Remote Similarity	NPC476782
0.6742	Remote Similarity	NPC476781
0.6739	Remote Similarity	NPC212340
0.6737	Remote Similarity	NPC475773
0.6737	Remote Similarity	NPC239938
0.6735	Remote Similarity	NPC473520
0.6729	Remote Similarity	NPC475463
0.6707	Remote Similarity	NPC314103
0.6705	Remote Similarity	NPC179922
0.6703	Remote Similarity	NPC267592
0.6701	Remote Similarity	NPC478004
0.6701	Remote Similarity	NPC474323
0.6701	Remote Similarity	NPC158388
0.6701	Remote Similarity	NPC470114
0.6701	Remote Similarity	NPC478003
0.6701	Remote Similarity	NPC206614
0.6699	Remote Similarity	NPC227622
0.6699	Remote Similarity	NPC80144
0.6667	Remote Similarity	NPC477332
0.6667	Remote Similarity	NPC472352
0.6667	Remote Similarity	NPC474266
0.6667	Remote Similarity	NPC225748
0.6667	Remote Similarity	NPC477759
0.6667	Remote Similarity	NPC215408
0.6667	Remote Similarity	NPC169085
0.6667	Remote Similarity	NPC477754
0.6667	Remote Similarity	NPC9763
0.6667	Remote Similarity	NPC477761
0.6667	Remote Similarity	NPC477760
0.6667	Remote Similarity	NPC470424
0.6667	Remote Similarity	NPC60849
0.6667	Remote Similarity	NPC477758
0.6667	Remote Similarity	NPC163812
0.6667	Remote Similarity	NPC473146
0.6667	Remote Similarity	NPC39266
0.6667	Remote Similarity	NPC476435
0.6635	Remote Similarity	NPC473148
0.6634	Remote Similarity	NPC74466
0.6634	Remote Similarity	NPC470632
0.6634	Remote Similarity	NPC472273
0.6634	Remote Similarity	NPC472145
0.6633	Remote Similarity	NPC12172
0.6633	Remote Similarity	NPC208886
0.6633	Remote Similarity	NPC329952
0.6633	Remote Similarity	NPC472197
0.6629	Remote Similarity	NPC477350
0.6606	Remote Similarity	NPC312498
0.6606	Remote Similarity	NPC473849
0.6602	Remote Similarity	NPC476611

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 NPC473791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	829
0.1-0.2	4379
0.2-0.3	2666
0.3-0.4	832
0.4-0.5	346
0.5-0.6	92
0.6-0.7	6
0.7-0.8	0
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
0.7059	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7909	Approved
0.6699	Remote Similarity	NPD8082	Approved
0.6699	Remote Similarity	NPD8138	Approved
0.6699	Remote Similarity	NPD8139	Approved
0.6699	Remote Similarity	NPD8084	Approved
0.6699	Remote Similarity	NPD8083	Approved
0.6699	Remote Similarity	NPD8086	Approved
0.6699	Remote Similarity	NPD8085	Approved
0.6667	Remote Similarity	NPD8393	Approved
0.6635	Remote Similarity	NPD8275	Approved
0.6635	Remote Similarity	NPD8276	Approved
0.6571	Remote Similarity	NPD8081	Approved
0.6571	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3669	Approved
0.6489	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD4238	Approved
0.6304	Remote Similarity	NPD4802	Phase 2
0.63	Remote Similarity	NPD7983	Approved
0.6293	Remote Similarity	NPD8266	Approved
0.6293	Remote Similarity	NPD8268	Approved
0.6293	Remote Similarity	NPD8269	Approved
0.6293	Remote Similarity	NPD8267	Approved
0.6279	Remote Similarity	NPD898	Approved
0.6279	Remote Similarity	NPD897	Approved
0.6279	Remote Similarity	NPD896	Approved
0.6277	Remote Similarity	NPD1780	Approved
0.6277	Remote Similarity	NPD1779	Approved
0.625	Remote Similarity	NPD2267	Suspended
0.625	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD3728	Approved
0.6203	Remote Similarity	NPD3730	Approved
0.6182	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD8307	Discontinued
0.6147	Remote Similarity	NPD8140	Approved
0.6064	Remote Similarity	NPD7329	Approved
0.6047	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD8305	Approved
0.6036	Remote Similarity	NPD8306	Approved
0.6024	Remote Similarity	NPD3198	Approved
0.6023	Remote Similarity	NPD229	Approved
0.6	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8087	Discontinued
0.5934	Remote Similarity	NPD3181	Approved
0.5929	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8515	Approved
0.5882	Remote Similarity	NPD8513	Phase 3
0.5882	Remote Similarity	NPD6698	Approved
0.5882	Remote Similarity	NPD46	Approved
0.5882	Remote Similarity	NPD8516	Approved
0.5882	Remote Similarity	NPD8517	Approved
0.5876	Remote Similarity	NPD6435	Approved
0.5856	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1700	Approved
0.5812	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6686	Approved
0.5794	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.578	Remote Similarity	NPD8300	Approved
0.578	Remote Similarity	NPD8301	Approved
0.5763	Remote Similarity	NPD7641	Discontinued
0.575	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7345	Approved
0.5702	Remote Similarity	NPD8080	Discontinued
0.569	Remote Similarity	NPD8133	Approved
0.567	Remote Similarity	NPD5368	Approved
0.5663	Remote Similarity	NPD73	Approved
0.5656	Remote Similarity	NPD8328	Phase 3
0.5644	Remote Similarity	NPD5786	Approved
0.5632	Remote Similarity	NPD8961	Approved
0.562	Remote Similarity	NPD8444	Approved
0.5619	Remote Similarity	NPD8171	Discontinued
0.561	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7839	Suspended

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