NPASS Compound

Structure

CID27814 OpenBabel06191715352D 28 31 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2084 1.8750 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.0860 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4265 1.2515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 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 2 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 -1.0376 1.2515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.5860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2557 1.8750 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.5860 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 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 1 1 1 0 0 0 10 12 1 0 0 0 0 11 2 1 1 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 6 0 0 0 13 21 1 1 0 0 0 14 20 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 1 0 0 0 15 28 1 0 0 0 0 16 23 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 1 0 0 0 18 27 1 6 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 21 3 1 6 0 0 0 22 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	399.674
LogP:	2.808
LogD:	3.155
LogS:	-3.733
# Rotatable Bonds:	2
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.727
Synthetic Accessibility Score:	5.281
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.708
MDCK Permeability:	6.237842899281532e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.632
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.858
Plasma Protein Binding (PPB):	50.57682800292969%
Volume Distribution (VD):	0.603
Pgp-substrate:	31.220266342163086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.922
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.624
CYP3A4-substrate:	0.506

ADMET: Excretion

Clearance (CL):	13.77
Half-life (T1/2):	0.426

ADMET: Toxicity

hERG Blockers:	0.151
Human Hepatotoxicity (H-HT):	0.667
Drug-inuced Liver Injury (DILI):	0.245
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.122
Skin Sensitization:	0.683
Carcinogencity:	0.286
Eye Corrosion:	0.201
Eye Irritation:	0.045
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC27814

Natural Product ID:	NPC27814
*Common Name:**	Nigakilactone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DCUOEDHQKMLWHI-PJZZLEGSSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10-13,15,17-19,24H,8-9H2,1-6H3/t10-,11-,12+,13+,15-,17-,18+,19+,21-,22+/m1/s1
SMILES:	C[C@@H]1C=C(C(=O)[C@@]2(C)[C@H]1C[C@@H]1[C@@]3(C)[C@@H](CC(=O)O1)[C@@H](C)[C@@H]([C@H]([C@H]23)O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2228444
PubChem CID:	12313347
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16730421]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO704	Quassia amara	Species	Simaroubaceae	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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	10.0	%	PMID[523399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	3.2	%	PMID[523399]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	6.7	%	PMID[523399]

☑ 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 NPC27814 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	250
0.1-0.2	1628
0.2-0.3	4678
0.3-0.4	8220
0.4-0.5	12481
0.5-0.6	7737
0.6-0.7	5139
0.7-0.8	2340
0.8-0.85	167
0.85-0.9	52
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9174	High Similarity	NPC127530
0.9065	High Similarity	NPC198539
0.9038	High Similarity	NPC202524
0.9009	High Similarity	NPC275675
0.8972	High Similarity	NPC90769
0.8952	High Similarity	NPC293850
0.8899	High Similarity	NPC251236
0.8899	High Similarity	NPC328374
0.8899	High Similarity	NPC96312
0.8899	High Similarity	NPC40632
0.8857	High Similarity	NPC3316
0.8857	High Similarity	NPC144854
0.885	High Similarity	NPC227397
0.8829	High Similarity	NPC473920
0.8829	High Similarity	NPC470777
0.8829	High Similarity	NPC279143
0.8807	High Similarity	NPC18547
0.8807	High Similarity	NPC474906
0.8807	High Similarity	NPC473798
0.8774	High Similarity	NPC154608
0.8774	High Similarity	NPC192813
0.8774	High Similarity	NPC277017
0.8727	High Similarity	NPC134869
0.8727	High Similarity	NPC173686
0.8727	High Similarity	NPC16081
0.8727	High Similarity	NPC235539
0.8727	High Similarity	NPC152199
0.8716	High Similarity	NPC49451
0.8704	High Similarity	NPC201992
0.8641	High Similarity	NPC104861
0.8636	High Similarity	NPC45218
0.8636	High Similarity	NPC323821
0.8636	High Similarity	NPC143268
0.8636	High Similarity	NPC268238
0.8624	High Similarity	NPC11252
0.8624	High Similarity	NPC289312
0.8585	High Similarity	NPC102352
0.8585	High Similarity	NPC181357
0.8584	High Similarity	NPC109607
0.8584	High Similarity	NPC107338
0.8571	High Similarity	NPC176005
0.8571	High Similarity	NPC297179
0.8571	High Similarity	NPC275583
0.8571	High Similarity	NPC17772
0.8547	High Similarity	NPC475636
0.8547	High Similarity	NPC295220
0.8545	High Similarity	NPC7921
0.8545	High Similarity	NPC208998
0.8545	High Similarity	NPC51978
0.8532	High Similarity	NPC146945
0.8532	High Similarity	NPC171888
0.8522	High Similarity	NPC91693
0.8522	High Similarity	NPC18945
0.8522	High Similarity	NPC265557
0.8522	High Similarity	NPC105926
0.8519	High Similarity	NPC310546
0.8496	Intermediate Similarity	NPC475775
0.8496	Intermediate Similarity	NPC476529
0.8482	Intermediate Similarity	NPC287343
0.8482	Intermediate Similarity	NPC97908
0.8482	Intermediate Similarity	NPC470854
0.8482	Intermediate Similarity	NPC122033
0.8482	Intermediate Similarity	NPC309433
0.8482	Intermediate Similarity	NPC474654
0.8475	Intermediate Similarity	NPC54614
0.8475	Intermediate Similarity	NPC309096
0.8462	Intermediate Similarity	NPC472972
0.8448	Intermediate Similarity	NPC476729
0.8448	Intermediate Similarity	NPC24651
0.844	Intermediate Similarity	NPC210005
0.8435	Intermediate Similarity	NPC312833
0.8421	Intermediate Similarity	NPC478051
0.8407	Intermediate Similarity	NPC251310
0.8396	Intermediate Similarity	NPC179208
0.8396	Intermediate Similarity	NPC264048
0.8396	Intermediate Similarity	NPC95585
0.8396	Intermediate Similarity	NPC282233
0.8393	Intermediate Similarity	NPC474734
0.8349	Intermediate Similarity	NPC474242
0.8349	Intermediate Similarity	NPC141350
0.8333	Intermediate Similarity	NPC469488
0.8319	Intermediate Similarity	NPC473590
0.8318	Intermediate Similarity	NPC65523
0.8318	Intermediate Similarity	NPC40170
0.8304	Intermediate Similarity	NPC469877
0.8304	Intermediate Similarity	NPC470919
0.8304	Intermediate Similarity	NPC243354
0.8291	Intermediate Similarity	NPC470922
0.8291	Intermediate Similarity	NPC473255
0.8288	Intermediate Similarity	NPC474516
0.8276	Intermediate Similarity	NPC471965
0.8273	Intermediate Similarity	NPC239097
0.8246	Intermediate Similarity	NPC188667
0.8246	Intermediate Similarity	NPC204552
0.823	Intermediate Similarity	NPC474046
0.823	Intermediate Similarity	NPC478216
0.823	Intermediate Similarity	NPC207217
0.823	Intermediate Similarity	NPC259306
0.823	Intermediate Similarity	NPC470628
0.822	Intermediate Similarity	NPC87662
0.822	Intermediate Similarity	NPC477745
0.8214	Intermediate Similarity	NPC194273
0.8214	Intermediate Similarity	NPC255017
0.8214	Intermediate Similarity	NPC194100
0.8205	Intermediate Similarity	NPC471961
0.8205	Intermediate Similarity	NPC202666
0.8205	Intermediate Similarity	NPC14617
0.8205	Intermediate Similarity	NPC67251
0.8205	Intermediate Similarity	NPC471964
0.8205	Intermediate Similarity	NPC262199
0.8198	Intermediate Similarity	NPC34315
0.8198	Intermediate Similarity	NPC471243
0.819	Intermediate Similarity	NPC470779
0.819	Intermediate Similarity	NPC477046
0.819	Intermediate Similarity	NPC102822
0.8182	Intermediate Similarity	NPC41405
0.8165	Intermediate Similarity	NPC230541
0.8158	Intermediate Similarity	NPC473968
0.8151	Intermediate Similarity	NPC470882
0.8151	Intermediate Similarity	NPC476008
0.8142	Intermediate Similarity	NPC247069
0.8136	Intermediate Similarity	NPC177820
0.8136	Intermediate Similarity	NPC247315
0.8136	Intermediate Similarity	NPC30188
0.8136	Intermediate Similarity	NPC471962
0.8136	Intermediate Similarity	NPC471963
0.8125	Intermediate Similarity	NPC152117
0.8125	Intermediate Similarity	NPC234042
0.8125	Intermediate Similarity	NPC193948
0.8125	Intermediate Similarity	NPC205534
0.8125	Intermediate Similarity	NPC302146
0.8125	Intermediate Similarity	NPC472002
0.812	Intermediate Similarity	NPC65858
0.8108	Intermediate Similarity	NPC100908
0.8103	Intermediate Similarity	NPC112038
0.8091	Intermediate Similarity	NPC289702
0.8091	Intermediate Similarity	NPC208461
0.8091	Intermediate Similarity	NPC94942
0.8091	Intermediate Similarity	NPC275539
0.8091	Intermediate Similarity	NPC189075
0.8091	Intermediate Similarity	NPC272576
0.8087	Intermediate Similarity	NPC470776
0.8087	Intermediate Similarity	NPC286347
0.8073	Intermediate Similarity	NPC96377
0.807	Intermediate Similarity	NPC270958
0.8067	Intermediate Similarity	NPC285091
0.8065	Intermediate Similarity	NPC190065
0.8065	Intermediate Similarity	NPC141215
0.8065	Intermediate Similarity	NPC471089
0.8056	Intermediate Similarity	NPC209298
0.8056	Intermediate Similarity	NPC277074
0.8056	Intermediate Similarity	NPC478057
0.8053	Intermediate Similarity	NPC320118
0.8053	Intermediate Similarity	NPC202889
0.8053	Intermediate Similarity	NPC250109
0.8053	Intermediate Similarity	NPC962
0.8051	Intermediate Similarity	NPC135038
0.8051	Intermediate Similarity	NPC43252
0.8051	Intermediate Similarity	NPC267822
0.8037	Intermediate Similarity	NPC252614
0.8036	Intermediate Similarity	NPC100329
0.8036	Intermediate Similarity	NPC188738
0.8036	Intermediate Similarity	NPC247031
0.8036	Intermediate Similarity	NPC97939
0.8036	Intermediate Similarity	NPC132790
0.8033	Intermediate Similarity	NPC254614
0.8033	Intermediate Similarity	NPC100390
0.8033	Intermediate Similarity	NPC476193
0.8018	Intermediate Similarity	NPC478210
0.8018	Intermediate Similarity	NPC472534
0.8018	Intermediate Similarity	NPC143706
0.8017	Intermediate Similarity	NPC469945
0.8017	Intermediate Similarity	NPC309780
0.8017	Intermediate Similarity	NPC6377
0.8017	Intermediate Similarity	NPC35405
0.8017	Intermediate Similarity	NPC214484
0.8017	Intermediate Similarity	NPC114441
0.8017	Intermediate Similarity	NPC475171
0.8017	Intermediate Similarity	NPC473203
0.8017	Intermediate Similarity	NPC11551
0.8017	Intermediate Similarity	NPC208381
0.8017	Intermediate Similarity	NPC39211
0.8017	Intermediate Similarity	NPC258592
0.8017	Intermediate Similarity	NPC473401
0.8017	Intermediate Similarity	NPC477196
0.8017	Intermediate Similarity	NPC472949
0.8017	Intermediate Similarity	NPC473884
0.8017	Intermediate Similarity	NPC180550
0.8017	Intermediate Similarity	NPC192791
0.8017	Intermediate Similarity	NPC178548
0.8017	Intermediate Similarity	NPC157868
0.8017	Intermediate Similarity	NPC475041
0.8017	Intermediate Similarity	NPC319570
0.8	Intermediate Similarity	NPC473265
0.8	Intermediate Similarity	NPC110496
0.8	Intermediate Similarity	NPC219353
0.8	Intermediate Similarity	NPC295885
0.8	Intermediate Similarity	NPC471474
0.8	Intermediate Similarity	NPC596
0.8	Intermediate Similarity	NPC470775

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 NPC27814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	1995
0.2-0.3	3730
0.3-0.4	1999
0.4-0.5	743
0.5-0.6	233
0.6-0.7	133
0.7-0.8	89
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD8328	Phase 3
0.8091	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD4632	Approved
0.7965	Intermediate Similarity	NPD8297	Approved
0.7949	Intermediate Similarity	NPD6319	Approved
0.7928	Intermediate Similarity	NPD6899	Approved
0.7928	Intermediate Similarity	NPD6881	Approved
0.7909	Intermediate Similarity	NPD6675	Approved
0.7909	Intermediate Similarity	NPD5739	Approved
0.7909	Intermediate Similarity	NPD6402	Approved
0.7909	Intermediate Similarity	NPD7128	Approved
0.7876	Intermediate Similarity	NPD6649	Approved
0.7876	Intermediate Similarity	NPD6650	Approved
0.7857	Intermediate Similarity	NPD6372	Approved
0.7857	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6373	Approved
0.7845	Intermediate Similarity	NPD6009	Approved
0.7845	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD5697	Approved
0.7788	Intermediate Similarity	NPD7290	Approved
0.7788	Intermediate Similarity	NPD7102	Approved
0.7788	Intermediate Similarity	NPD6883	Approved
0.7768	Intermediate Similarity	NPD6011	Approved
0.7768	Intermediate Similarity	NPD7320	Approved
0.7757	Intermediate Similarity	NPD7902	Approved
0.775	Intermediate Similarity	NPD7604	Phase 2
0.7731	Intermediate Similarity	NPD5983	Phase 2
0.7719	Intermediate Similarity	NPD8130	Phase 1
0.7719	Intermediate Similarity	NPD6847	Approved
0.7719	Intermediate Similarity	NPD6869	Approved
0.7719	Intermediate Similarity	NPD6617	Approved
0.7699	Intermediate Similarity	NPD6013	Approved
0.7699	Intermediate Similarity	NPD6014	Approved
0.7699	Intermediate Similarity	NPD6012	Approved
0.7686	Intermediate Similarity	NPD7492	Approved
0.7679	Intermediate Similarity	NPD5701	Approved
0.7652	Intermediate Similarity	NPD6882	Approved
0.7647	Intermediate Similarity	NPD6054	Approved
0.7642	Intermediate Similarity	NPD7736	Approved
0.7642	Intermediate Similarity	NPD7748	Approved
0.7623	Intermediate Similarity	NPD6616	Approved
0.7623	Intermediate Similarity	NPD6336	Discontinued
0.7619	Intermediate Similarity	NPD7515	Phase 2
0.7565	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7078	Approved
0.7522	Intermediate Similarity	NPD6412	Phase 2
0.7521	Intermediate Similarity	NPD6370	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.7477	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7900	Approved
0.7438	Intermediate Similarity	NPD6016	Approved
0.7438	Intermediate Similarity	NPD6015	Approved
0.7419	Intermediate Similarity	NPD8293	Discontinued
0.7404	Intermediate Similarity	NPD3573	Approved
0.7391	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5988	Approved
0.7339	Intermediate Similarity	NPD5221	Approved
0.7339	Intermediate Similarity	NPD4697	Phase 3
0.7339	Intermediate Similarity	NPD5222	Approved
0.7339	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6335	Approved
0.7328	Intermediate Similarity	NPD4634	Approved
0.7311	Intermediate Similarity	NPD6274	Approved
0.7311	Intermediate Similarity	NPD6868	Approved
0.7304	Intermediate Similarity	NPD6686	Approved
0.7297	Intermediate Similarity	NPD5285	Approved
0.7297	Intermediate Similarity	NPD5286	Approved
0.7297	Intermediate Similarity	NPD4696	Approved
0.7295	Intermediate Similarity	NPD6921	Approved
0.729	Intermediate Similarity	NPD6079	Approved
0.7281	Intermediate Similarity	NPD6008	Approved
0.7273	Intermediate Similarity	NPD7101	Approved
0.7273	Intermediate Similarity	NPD4755	Approved
0.7273	Intermediate Similarity	NPD6083	Phase 2
0.7273	Intermediate Similarity	NPD5173	Approved
0.7273	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD7100	Approved
0.7264	Intermediate Similarity	NPD5328	Approved
0.725	Intermediate Similarity	NPD7115	Discovery
0.725	Intermediate Similarity	NPD6317	Approved
0.7232	Intermediate Similarity	NPD5223	Approved
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7207	Intermediate Similarity	NPD7638	Approved
0.72	Intermediate Similarity	NPD7507	Approved
0.719	Intermediate Similarity	NPD6313	Approved
0.719	Intermediate Similarity	NPD6314	Approved
0.7179	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5737	Approved
0.717	Intermediate Similarity	NPD6672	Approved
0.7168	Intermediate Similarity	NPD4633	Approved
0.7168	Intermediate Similarity	NPD5225	Approved
0.7168	Intermediate Similarity	NPD5211	Phase 2
0.7168	Intermediate Similarity	NPD5224	Approved
0.7168	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD4700	Approved
0.7105	Intermediate Similarity	NPD5174	Approved
0.7105	Intermediate Similarity	NPD5175	Approved
0.7103	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6033	Approved
0.7054	Intermediate Similarity	NPD5696	Approved
0.7043	Intermediate Similarity	NPD5141	Approved
0.7031	Intermediate Similarity	NPD7319	Approved
0.7016	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6908	Approved
0.7016	Intermediate Similarity	NPD6909	Approved
0.6957	Remote Similarity	NPD4754	Approved
0.6937	Remote Similarity	NPD5695	Phase 3
0.6923	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7260	Phase 2
0.6903	Remote Similarity	NPD4225	Approved
0.6893	Remote Similarity	NPD4695	Discontinued
0.688	Remote Similarity	NPD7503	Approved
0.6864	Remote Similarity	NPD4729	Approved
0.6864	Remote Similarity	NPD4730	Approved
0.6864	Remote Similarity	NPD5128	Approved
0.6857	Remote Similarity	NPD6110	Phase 1
0.6852	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4768	Approved
0.6838	Remote Similarity	NPD4767	Approved
0.6822	Remote Similarity	NPD7521	Approved
0.6822	Remote Similarity	NPD6409	Approved
0.6822	Remote Similarity	NPD6684	Approved
0.6822	Remote Similarity	NPD7146	Approved
0.6822	Remote Similarity	NPD5330	Approved
0.6822	Remote Similarity	NPD7334	Approved
0.6818	Remote Similarity	NPD8034	Phase 2
0.6818	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD8035	Phase 2
0.6789	Remote Similarity	NPD6080	Approved
0.6789	Remote Similarity	NPD6673	Approved
0.6789	Remote Similarity	NPD6904	Approved
0.6757	Remote Similarity	NPD4202	Approved
0.675	Remote Similarity	NPD5249	Phase 3
0.675	Remote Similarity	NPD5135	Approved
0.675	Remote Similarity	NPD5247	Approved
0.675	Remote Similarity	NPD5248	Approved
0.675	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5250	Approved
0.675	Remote Similarity	NPD5169	Approved
0.675	Remote Similarity	NPD5251	Approved
0.6742	Remote Similarity	NPD6845	Suspended
0.6724	Remote Similarity	NPD7632	Discontinued
0.6723	Remote Similarity	NPD5168	Approved
0.672	Remote Similarity	NPD7516	Approved
0.6697	Remote Similarity	NPD6903	Approved
0.6696	Remote Similarity	NPD5282	Discontinued
0.6694	Remote Similarity	NPD5215	Approved
0.6694	Remote Similarity	NPD5216	Approved
0.6694	Remote Similarity	NPD5217	Approved
0.6694	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6067	Discontinued
0.664	Remote Similarity	NPD7328	Approved
0.664	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD6053	Discontinued
0.6637	Remote Similarity	NPD4629	Approved
0.6637	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD3665	Phase 1
0.6636	Remote Similarity	NPD4786	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3666	Approved
0.6636	Remote Similarity	NPD3133	Approved
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD4753	Phase 2
0.6618	Remote Similarity	NPD6334	Approved
0.6618	Remote Similarity	NPD6333	Approved
0.6604	Remote Similarity	NPD3667	Approved
0.6585	Remote Similarity	NPD8133	Approved
0.6579	Remote Similarity	NPD7614	Phase 1
0.6577	Remote Similarity	NPD46	Approved
0.6577	Remote Similarity	NPD6698	Approved
0.6574	Remote Similarity	NPD1694	Approved
0.6574	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3617	Approved
0.6535	Remote Similarity	NPD8377	Approved
0.6535	Remote Similarity	NPD8294	Approved
0.6532	Remote Similarity	NPD5167	Approved
0.6518	Remote Similarity	NPD6050	Approved
0.6518	Remote Similarity	NPD5693	Phase 1
0.6514	Remote Similarity	NPD6098	Approved
0.6514	Remote Similarity	NPD5279	Phase 3
0.6496	Remote Similarity	NPD5344	Discontinued
0.6484	Remote Similarity	NPD8379	Approved
0.6484	Remote Similarity	NPD8513	Phase 3
0.6484	Remote Similarity	NPD8515	Approved
0.6484	Remote Similarity	NPD8378	Approved
0.6484	Remote Similarity	NPD8380	Approved
0.6484	Remote Similarity	NPD8033	Approved
0.6484	Remote Similarity	NPD8296	Approved
0.6484	Remote Similarity	NPD8516	Approved
0.6484	Remote Similarity	NPD8517	Approved
0.6484	Remote Similarity	NPD8335	Approved
0.646	Remote Similarity	NPD5778	Approved
0.646	Remote Similarity	NPD5779	Approved
0.6435	Remote Similarity	NPD7732	Phase 3
0.6429	Remote Similarity	NPD5692	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