NPASS Compound

Structure

NPC60315 OpenBabel07101719252D 50 52 0 0 1 0 0 0 0 0999 V2000 -4.8364 -4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3124 5.9086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6483 2.3920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3054 -2.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0182 -3.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1123 -1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4665 1.1029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2954 0.1738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8364 -4.1808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5349 4.9337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 1.6488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3364 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8019 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0085 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 -3.3147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5139 -0.6235 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 1.3272 -2.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4888 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1011 2.0338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0244 3.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0303 0.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8364 -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 2 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 3.9227 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4888 1.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5139 1.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 5.7246 2.8156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9800 2.9838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3612 1.2330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3364 -1.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9227 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1123 2.1828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2914 2.5984 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 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 22 1 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 23 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 21 38 1 0 0 0 0 23 33 1 0 0 0 0 24 40 2 0 0 0 0 24 46 1 0 0 0 0 25 32 1 0 0 0 0 25 38 1 6 0 0 0 26 39 1 1 0 0 0 26 47 1 0 0 0 0 27 41 2 0 0 0 0 27 47 1 0 0 0 0 28 42 2 0 0 0 0 28 49 1 0 0 0 0 29 43 2 0 0 0 0 29 50 1 0 0 0 0 30 44 2 0 0 0 0 30 48 1 0 0 0 0 31 22 1 1 0 0 0 31 32 1 0 0 0 0 31 34 1 0 0 0 0 32 39 1 1 0 0 0 33 35 1 0 0 0 0 33 45 1 1 0 0 0 34 37 1 0 0 0 0 34 48 1 1 0 0 0 35 36 1 0 0 0 0 35 46 1 1 0 0 0 36 38 1 6 0 0 0 36 49 1 0 0 0 0 37 39 1 6 0 0 0 37 50 1 0 0 0 0 38 9 1 6 0 0 0 39 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.32
Volume:	509.269
LogP:	4.137
LogD:	3.036
LogS:	-4.77
# Rotatable Bonds:	5
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	5.622
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.399
MDCK Permeability:	2.148834209947381e-05
Pgp-inhibitor:	0.23
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.319
Plasma Protein Binding (PPB):	92.8305892944336%
Volume Distribution (VD):	0.719
Pgp-substrate:	4.0499444007873535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.738
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.345
CYP3A4-inhibitor:	0.442
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	5.902
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.58
Drug-inuced Liver Injury (DILI):	0.131
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.226
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.849
Carcinogencity:	0.772
Eye Corrosion:	0.005
Eye Irritation:	0.06
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC60315

Natural Product ID:	NPC60315
*Common Name:**	Gagunin K
IUPAC Name:	[(1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aR,10bS)-7-acetyloxy-3,4,6-tri(butanoyloxy)-8-hydroxy-3a,5a,9-trimethyl-1-propan-2-yl-1,2,3,4,5,6,7,8,10a,10b-decahydrocyclohepta[e]inden-2-yl] pentanoate
Synonyms:	Gagunin K
Standard InCHIKey:	INJPRTBCZDYGGA-KONRAZDYSA-N
Standard InCHI:	InChI=1S/C39H62O11/c1-11-15-19-30(44)48-34-31(22(5)6)32-25-20-23(7)33(45)35(46-24(8)40)36(49-28(42)17-13-3)38(25,9)21-26(47-27(41)16-12-2)39(32,10)37(34)50-29(43)18-14-4/h20,22,25-26,31-37,45H,11-19,21H2,1-10H3/t25-,26+,31-,32+,33+,34-,35+,36-,37+,38-,39+/m1/s1
SMILES:	CCCCC(=O)O[C@@H]1[C@H](C(C)C)[C@H]2[C@]([C@H]1OC(=O)CCC)(C)[C@@H](OC(=O)CCC)C[C@@]1([C@@H]2C=C(C)[C@@H]([C@@H]([C@H]1OC(=O)CCC)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499960
PubChem CID:	25135701
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32676	phorbas sp.	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18811205]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	17.5	ug.mL-1	PMID[468718]
NPT2	Others	Unspecified		LC50	=	55.0	ug.mL-1	PMID[468718]

☑ 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 NPC60315 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	196
0.1-0.2	1246
0.2-0.3	4322
0.3-0.4	9973
0.4-0.5	11889
0.5-0.6	6152
0.6-0.7	6778
0.7-0.8	2074
0.8-0.85	51
0.85-0.9	0
0.9-0.95	3
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC80809
0.9897	High Similarity	NPC181104
0.9897	High Similarity	NPC475331
0.9897	High Similarity	NPC121518
0.9897	High Similarity	NPC475335
0.9897	High Similarity	NPC103298
0.9897	High Similarity	NPC201144
0.9897	High Similarity	NPC288502
0.9794	High Similarity	NPC473694
0.9794	High Similarity	NPC475623
0.9794	High Similarity	NPC475334
0.9596	High Similarity	NPC475290
0.9495	High Similarity	NPC475585
0.9495	High Similarity	NPC473577
0.9495	High Similarity	NPC474550
0.8491	Intermediate Similarity	NPC472217
0.8491	Intermediate Similarity	NPC472219
0.8491	Intermediate Similarity	NPC472218
0.8491	Intermediate Similarity	NPC88701
0.8476	Intermediate Similarity	NPC470980
0.8462	Intermediate Similarity	NPC474124
0.8381	Intermediate Similarity	NPC473543
0.8365	Intermediate Similarity	NPC476471
0.8365	Intermediate Similarity	NPC475344
0.8333	Intermediate Similarity	NPC475033
0.8333	Intermediate Similarity	NPC475032
0.8317	Intermediate Similarity	NPC292178
0.8317	Intermediate Similarity	NPC86893
0.8286	Intermediate Similarity	NPC473523
0.8269	Intermediate Similarity	NPC155974
0.8269	Intermediate Similarity	NPC475617
0.8257	Intermediate Similarity	NPC473921
0.8257	Intermediate Similarity	NPC475668
0.8257	Intermediate Similarity	NPC475480
0.8241	Intermediate Similarity	NPC5475
0.8241	Intermediate Similarity	NPC173905
0.8241	Intermediate Similarity	NPC472216
0.8241	Intermediate Similarity	NPC284828
0.8218	Intermediate Similarity	NPC474922
0.8218	Intermediate Similarity	NPC473258
0.8208	Intermediate Similarity	NPC152966
0.8198	Intermediate Similarity	NPC43213
0.8198	Intermediate Similarity	NPC216665
0.819	Intermediate Similarity	NPC470972
0.8173	Intermediate Similarity	NPC208358
0.8165	Intermediate Similarity	NPC475134
0.8165	Intermediate Similarity	NPC475563
0.8155	Intermediate Similarity	NPC254121
0.8113	Intermediate Similarity	NPC85742
0.8108	Intermediate Similarity	NPC250109
0.8108	Intermediate Similarity	NPC962
0.8095	Intermediate Similarity	NPC289670
0.8077	Intermediate Similarity	NPC470067
0.8077	Intermediate Similarity	NPC470066
0.8073	Intermediate Similarity	NPC218853
0.807	Intermediate Similarity	NPC255081
0.807	Intermediate Similarity	NPC275696
0.807	Intermediate Similarity	NPC5991
0.807	Intermediate Similarity	NPC22628
0.807	Intermediate Similarity	NPC471108
0.807	Intermediate Similarity	NPC5989
0.8061	Intermediate Similarity	NPC477668
0.8058	Intermediate Similarity	NPC306797
0.8058	Intermediate Similarity	NPC111834
0.8058	Intermediate Similarity	NPC253115
0.8058	Intermediate Similarity	NPC169270
0.8058	Intermediate Similarity	NPC54248
0.8058	Intermediate Similarity	NPC276103
0.8058	Intermediate Similarity	NPC475304
0.8058	Intermediate Similarity	NPC304899
0.8058	Intermediate Similarity	NPC292718
0.8039	Intermediate Similarity	NPC39453
0.8036	Intermediate Similarity	NPC220293
0.8036	Intermediate Similarity	NPC472400
0.8036	Intermediate Similarity	NPC178289
0.8019	Intermediate Similarity	NPC200672
0.8019	Intermediate Similarity	NPC252242
0.8019	Intermediate Similarity	NPC475956
0.8019	Intermediate Similarity	NPC214714
0.8018	Intermediate Similarity	NPC280782
0.8	Intermediate Similarity	NPC6206
0.8	Intermediate Similarity	NPC475877
0.8	Intermediate Similarity	NPC129340
0.8	Intermediate Similarity	NPC230546
0.8	Intermediate Similarity	NPC167974
0.8	Intermediate Similarity	NPC238850
0.8	Intermediate Similarity	NPC272223
0.8	Intermediate Similarity	NPC251680
0.8	Intermediate Similarity	NPC250956
0.8	Intermediate Similarity	NPC473510
0.7982	Intermediate Similarity	NPC472758
0.7982	Intermediate Similarity	NPC471125
0.7982	Intermediate Similarity	NPC258323
0.7982	Intermediate Similarity	NPC472397
0.7982	Intermediate Similarity	NPC171905
0.7965	Intermediate Similarity	NPC266728
0.7965	Intermediate Similarity	NPC470075
0.7965	Intermediate Similarity	NPC49492
0.7963	Intermediate Similarity	NPC278628
0.7963	Intermediate Similarity	NPC231530
0.7961	Intermediate Similarity	NPC241047
0.7949	Intermediate Similarity	NPC129992
0.7946	Intermediate Similarity	NPC472757
0.7946	Intermediate Similarity	NPC251309
0.7944	Intermediate Similarity	NPC474775
0.7944	Intermediate Similarity	NPC260809
0.7944	Intermediate Similarity	NPC55954
0.7944	Intermediate Similarity	NPC218513
0.7944	Intermediate Similarity	NPC222153
0.7944	Intermediate Similarity	NPC474783
0.7931	Intermediate Similarity	NPC52839
0.7931	Intermediate Similarity	NPC202051
0.7928	Intermediate Similarity	NPC114188
0.7928	Intermediate Similarity	NPC285410
0.7928	Intermediate Similarity	NPC250481
0.7928	Intermediate Similarity	NPC470076
0.7928	Intermediate Similarity	NPC263827
0.7925	Intermediate Similarity	NPC476132
0.7925	Intermediate Similarity	NPC26557
0.7921	Intermediate Similarity	NPC470832
0.7921	Intermediate Similarity	NPC48732
0.7913	Intermediate Similarity	NPC475041
0.7913	Intermediate Similarity	NPC472667
0.7909	Intermediate Similarity	NPC265655
0.7909	Intermediate Similarity	NPC10064
0.7909	Intermediate Similarity	NPC40728
0.7909	Intermediate Similarity	NPC170221
0.7905	Intermediate Similarity	NPC119036
0.7905	Intermediate Similarity	NPC470068
0.7905	Intermediate Similarity	NPC102426
0.7905	Intermediate Similarity	NPC300179
0.7895	Intermediate Similarity	NPC10721
0.7895	Intermediate Similarity	NPC470171
0.7895	Intermediate Similarity	NPC156252
0.789	Intermediate Similarity	NPC67321
0.789	Intermediate Similarity	NPC187435
0.789	Intermediate Similarity	NPC475176
0.789	Intermediate Similarity	NPC475781
0.789	Intermediate Similarity	NPC469318
0.789	Intermediate Similarity	NPC473173
0.7885	Intermediate Similarity	NPC88009
0.7885	Intermediate Similarity	NPC284194
0.7885	Intermediate Similarity	NPC471765
0.7885	Intermediate Similarity	NPC211810
0.7885	Intermediate Similarity	NPC221801
0.7885	Intermediate Similarity	NPC475178
0.7876	Intermediate Similarity	NPC472274
0.787	Intermediate Similarity	NPC477812
0.787	Intermediate Similarity	NPC470768
0.787	Intermediate Similarity	NPC470838
0.787	Intermediate Similarity	NPC75608
0.7864	Intermediate Similarity	NPC472360
0.7864	Intermediate Similarity	NPC472416
0.7863	Intermediate Similarity	NPC19464
0.7863	Intermediate Similarity	NPC222688
0.7863	Intermediate Similarity	NPC269642
0.7863	Intermediate Similarity	NPC162009
0.7863	Intermediate Similarity	NPC257017
0.7857	Intermediate Similarity	NPC470063
0.7857	Intermediate Similarity	NPC233003
0.7857	Intermediate Similarity	NPC126691
0.7857	Intermediate Similarity	NPC477050
0.785	Intermediate Similarity	NPC165578
0.785	Intermediate Similarity	NPC471119
0.785	Intermediate Similarity	NPC22388
0.785	Intermediate Similarity	NPC470053
0.785	Intermediate Similarity	NPC473928
0.785	Intermediate Similarity	NPC472552
0.785	Intermediate Similarity	NPC474709
0.785	Intermediate Similarity	NPC296879
0.7845	Intermediate Similarity	NPC79579
0.7845	Intermediate Similarity	NPC471128
0.7845	Intermediate Similarity	NPC145182
0.7845	Intermediate Similarity	NPC157252
0.7845	Intermediate Similarity	NPC471126
0.7845	Intermediate Similarity	NPC471406
0.7838	Intermediate Similarity	NPC101450
0.7838	Intermediate Similarity	NPC472215
0.7838	Intermediate Similarity	NPC181298
0.7838	Intermediate Similarity	NPC472214
0.783	Intermediate Similarity	NPC476195
0.783	Intermediate Similarity	NPC38855
0.783	Intermediate Similarity	NPC477521
0.7826	Intermediate Similarity	NPC146280
0.7826	Intermediate Similarity	NPC472080
0.7826	Intermediate Similarity	NPC475372
0.7826	Intermediate Similarity	NPC124676
0.7822	Intermediate Similarity	NPC246028
0.7818	Intermediate Similarity	NPC94529
0.7818	Intermediate Similarity	NPC48548
0.7818	Intermediate Similarity	NPC128795
0.7818	Intermediate Similarity	NPC217921
0.7818	Intermediate Similarity	NPC195708
0.7818	Intermediate Similarity	NPC135015
0.7818	Intermediate Similarity	NPC295980
0.7818	Intermediate Similarity	NPC295389
0.781	Intermediate Similarity	NPC274793
0.781	Intermediate Similarity	NPC210337
0.781	Intermediate Similarity	NPC473244
0.7807	Intermediate Similarity	NPC146652

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 NPC60315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1631
0.2-0.3	3879
0.3-0.4	2303
0.4-0.5	675
0.5-0.6	229
0.6-0.7	227
0.7-0.8	38
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
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.7905	Intermediate Similarity	NPD7638	Approved
0.7627	Intermediate Similarity	NPD8033	Approved
0.7544	Intermediate Similarity	NPD8297	Approved
0.7542	Intermediate Similarity	NPD6319	Approved
0.7542	Intermediate Similarity	NPD8377	Approved
0.7542	Intermediate Similarity	NPD8294	Approved
0.7521	Intermediate Similarity	NPD7507	Approved
0.7521	Intermediate Similarity	NPD7328	Approved
0.7521	Intermediate Similarity	NPD7327	Approved
0.7479	Intermediate Similarity	NPD8380	Approved
0.7479	Intermediate Similarity	NPD8335	Approved
0.7479	Intermediate Similarity	NPD8379	Approved
0.7479	Intermediate Similarity	NPD8378	Approved
0.7479	Intermediate Similarity	NPD8296	Approved
0.7458	Intermediate Similarity	NPD7516	Approved
0.7407	Intermediate Similarity	NPD4225	Approved
0.7368	Intermediate Similarity	NPD6371	Approved
0.7364	Intermediate Similarity	NPD7632	Discontinued
0.7339	Intermediate Similarity	NPD7319	Approved
0.7333	Intermediate Similarity	NPD7637	Suspended
0.7328	Intermediate Similarity	NPD4632	Approved
0.7321	Intermediate Similarity	NPD6402	Approved
0.7321	Intermediate Similarity	NPD7128	Approved
0.7321	Intermediate Similarity	NPD5739	Approved
0.7321	Intermediate Similarity	NPD6675	Approved
0.7288	Intermediate Similarity	NPD7115	Discovery
0.7282	Intermediate Similarity	NPD4250	Approved
0.7282	Intermediate Similarity	NPD4251	Approved
0.7281	Intermediate Similarity	NPD6372	Approved
0.7281	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6399	Phase 3
0.7257	Intermediate Similarity	NPD6412	Phase 2
0.7193	Intermediate Similarity	NPD6899	Approved
0.7193	Intermediate Similarity	NPD6881	Approved
0.7193	Intermediate Similarity	NPD7320	Approved
0.7193	Intermediate Similarity	NPD6686	Approved
0.719	Intermediate Similarity	NPD7503	Approved
0.7184	Intermediate Similarity	NPD4249	Approved
0.7179	Intermediate Similarity	NPD8133	Approved
0.7177	Intermediate Similarity	NPD8293	Discontinued
0.717	Intermediate Similarity	NPD7983	Approved
0.7155	Intermediate Similarity	NPD8130	Phase 1
0.7155	Intermediate Similarity	NPD6650	Approved
0.7155	Intermediate Similarity	NPD6649	Approved
0.7154	Intermediate Similarity	NPD7492	Approved
0.712	Intermediate Similarity	NPD7736	Approved
0.7117	Intermediate Similarity	NPD5344	Discontinued
0.7115	Intermediate Similarity	NPD7524	Approved
0.7107	Intermediate Similarity	NPD6054	Approved
0.7107	Intermediate Similarity	NPD6059	Approved
0.7105	Intermediate Similarity	NPD5697	Approved
0.7105	Intermediate Similarity	NPD5701	Approved
0.7105	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4820	Approved
0.71	Intermediate Similarity	NPD4822	Approved
0.71	Intermediate Similarity	NPD4819	Approved
0.71	Intermediate Similarity	NPD4821	Approved
0.7097	Intermediate Similarity	NPD6616	Approved
0.7094	Intermediate Similarity	NPD6882	Approved
0.7094	Intermediate Similarity	NPD6053	Discontinued
0.7075	Intermediate Similarity	NPD46	Approved
0.7075	Intermediate Similarity	NPD6698	Approved
0.7071	Intermediate Similarity	NPD4271	Approved
0.7071	Intermediate Similarity	NPD4268	Approved
0.7069	Intermediate Similarity	NPD7102	Approved
0.7069	Intermediate Similarity	NPD7290	Approved
0.7069	Intermediate Similarity	NPD6883	Approved
0.7059	Intermediate Similarity	NPD5362	Discontinued
0.704	Intermediate Similarity	NPD7078	Approved
0.7018	Intermediate Similarity	NPD6008	Approved
0.7009	Intermediate Similarity	NPD8035	Phase 2
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD8034	Phase 2
0.7009	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.6992	Remote Similarity	NPD6370	Approved
0.699	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6013	Approved
0.6983	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6012	Approved
0.6983	Remote Similarity	NPD6014	Approved
0.6983	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD4634	Approved
0.6916	Remote Similarity	NPD7838	Discovery
0.6911	Remote Similarity	NPD5983	Phase 2
0.6911	Remote Similarity	NPD6015	Approved
0.6911	Remote Similarity	NPD6016	Approved
0.6903	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD6011	Approved
0.6893	Remote Similarity	NPD5331	Approved
0.6893	Remote Similarity	NPD5332	Approved
0.6893	Remote Similarity	NPD6695	Phase 3
0.6864	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4790	Discontinued
0.6855	Remote Similarity	NPD5988	Approved
0.6847	Remote Similarity	NPD4755	Approved
0.6827	Remote Similarity	NPD4786	Approved
0.6825	Remote Similarity	NPD6336	Discontinued
0.6818	Remote Similarity	NPD5695	Phase 3
0.6792	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7750	Discontinued
0.6789	Remote Similarity	NPD5779	Approved
0.6789	Remote Similarity	NPD4202	Approved
0.6789	Remote Similarity	NPD5778	Approved
0.6783	Remote Similarity	NPD5141	Approved
0.678	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7525	Registered
0.6762	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7154	Phase 3
0.6727	Remote Similarity	NPD7748	Approved
0.6726	Remote Similarity	NPD4700	Approved
0.6726	Remote Similarity	NPD5286	Approved
0.6726	Remote Similarity	NPD4696	Approved
0.6726	Remote Similarity	NPD6648	Approved
0.6726	Remote Similarity	NPD5285	Approved
0.6721	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7334	Approved
0.6698	Remote Similarity	NPD7521	Approved
0.6698	Remote Similarity	NPD6684	Approved
0.6698	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD7146	Approved
0.6698	Remote Similarity	NPD5330	Approved
0.6696	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6929	Approved
0.664	Remote Similarity	NPD8516	Approved
0.664	Remote Similarity	NPD8513	Phase 3
0.664	Remote Similarity	NPD8515	Approved
0.664	Remote Similarity	NPD8517	Approved
0.6639	Remote Similarity	NPD6274	Approved
0.6637	Remote Similarity	NPD5696	Approved
0.6635	Remote Similarity	NPD3667	Approved
0.6635	Remote Similarity	NPD4270	Approved
0.6635	Remote Similarity	NPD6435	Approved
0.6635	Remote Similarity	NPD4269	Approved
0.6613	Remote Similarity	NPD7100	Approved
0.6613	Remote Similarity	NPD7101	Approved
0.661	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5225	Approved
0.6609	Remote Similarity	NPD5224	Approved
0.6609	Remote Similarity	NPD5226	Approved
0.6609	Remote Similarity	NPD4633	Approved
0.6606	Remote Similarity	NPD5785	Approved
0.6602	Remote Similarity	NPD6931	Approved
0.6602	Remote Similarity	NPD6930	Phase 2
0.6589	Remote Similarity	NPD6033	Approved
0.6583	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4767	Approved
0.6581	Remote Similarity	NPD4768	Approved
0.6574	Remote Similarity	NPD6903	Approved
0.6574	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5174	Approved
0.6552	Remote Similarity	NPD5175	Approved
0.6545	Remote Similarity	NPD6079	Approved
0.6545	Remote Similarity	NPD7515	Phase 2
0.6542	Remote Similarity	NPD3618	Phase 1
0.6542	Remote Similarity	NPD5786	Approved
0.6535	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6335	Approved
0.6525	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5223	Approved
0.6518	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4753	Phase 2
0.6509	Remote Similarity	NPD3665	Phase 1
0.6509	Remote Similarity	NPD3133	Approved
0.6509	Remote Similarity	NPD3666	Approved
0.6508	Remote Similarity	NPD6908	Approved
0.6508	Remote Similarity	NPD6909	Approved
0.6491	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5776	Phase 2
0.6471	Remote Similarity	NPD4729	Approved
0.6471	Remote Similarity	NPD4730	Approved
0.6471	Remote Similarity	NPD6925	Approved
0.646	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6317	Approved
0.6449	Remote Similarity	NPD5363	Approved
0.6442	Remote Similarity	NPD5368	Approved
0.6442	Remote Similarity	NPD7514	Phase 3
0.6442	Remote Similarity	NPD4252	Approved
0.6436	Remote Similarity	NPD6942	Approved
0.6436	Remote Similarity	NPD7339	Approved
0.6429	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7900	Approved
0.6422	Remote Similarity	NPD5737	Approved
0.6422	Remote Similarity	NPD6672	Approved
0.641	Remote Similarity	NPD4754	Approved
0.6408	Remote Similarity	NPD6118	Approved
0.6408	Remote Similarity	NPD6697	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