NPASS Compound

Structure

NPC475290 OpenBabel07101718222D 49 51 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 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 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 4.9227 2.2321 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 0.0000 4.0000 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 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 0.0000 3.0000 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 2.8019 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 2.5139 -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 5.4227 1.3660 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 -1.8364 -2.4487 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 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 3.4888 1.4010 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 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 6.4227 1.3660 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 -2.3364 -1.5827 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 4.1123 2.1828 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 -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 21 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 23 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 26 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 22 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 20 37 1 0 0 0 0 22 33 1 0 0 0 0 23 39 2 0 0 0 0 23 45 1 0 0 0 0 24 31 1 0 0 0 0 24 37 1 6 0 0 0 25 38 1 1 0 0 0 25 46 1 0 0 0 0 26 40 2 0 0 0 0 26 46 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 48 1 0 0 0 0 29 43 2 0 0 0 0 29 49 1 0 0 0 0 30 21 1 1 0 0 0 30 31 1 0 0 0 0 30 34 1 0 0 0 0 31 38 1 1 0 0 0 32 33 1 0 0 0 0 32 35 1 0 0 0 0 32 44 1 1 0 0 0 33 45 1 1 0 0 0 34 36 1 0 0 0 0 34 47 1 1 0 0 0 35 37 1 6 0 0 0 35 48 1 0 0 0 0 36 38 1 6 0 0 0 36 49 1 0 0 0 0 37 9 1 6 0 0 0 38 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	692.41
Volume:	721.008
LogP:	5.574
LogD:	4.644
LogS:	-5.213
# Rotatable Bonds:	19
TPSA:	151.73
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.129
Synthetic Accessibility Score:	5.445
Fsp3:	0.816
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.727
MDCK Permeability:	7.713921513641253e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.856
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	89.38388061523438%
Volume Distribution (VD):	0.743
Pgp-substrate:	2.7708232402801514%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.149
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.169
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.804
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	9.127
Half-life (T1/2):	0.547

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.855
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.272
Carcinogencity:	0.017
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.488

Download Data

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

Natural Product: NPC475290

Natural Product ID:	NPC475290
*Common Name:**	Gagunin O
IUPAC Name:	[(1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aR,10bS)-8-acetyloxy-2,3,6-tri(butanoyloxy)-7-hydroxy-3a,5a,9-trimethyl-1-propan-2-yl-1,2,3,4,5,6,7,8,10a,10b-decahydrocyclohepta[e]inden-4-yl] butanoate
Synonyms:	Gagunin O
Standard InCHIKey:	MIKVSZXTTYIXJT-RLZBCHFNSA-N
Standard InCHI:	InChI=1S/C38H60O11/c1-11-15-26(40)46-25-20-37(9)24(19-22(7)33(45-23(8)39)32(44)35(37)48-28(42)17-13-3)31-30(21(5)6)34(47-27(41)16-12-2)36(38(25,31)10)49-29(43)18-14-4/h19,21,24-25,30-36,44H,11-18,20H2,1-10H3/t24-,25+,30-,31+,32+,33+,34-,35-,36+,37-,38+/m1/s1
SMILES:	CCCC(=O)OC1CC2(C(C=C(C(C(C2OC(=O)CCC)O)OC(=O)C)C)C3C1(C(C(C3C(C)C)OC(=O)CCC)OC(=O)CCC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502954
PubChem CID:	25135805
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	=	11.1	ug.mL-1	PMID[469058]
NPT2	Others	Unspecified		LC50	=	55.0	ug.mL-1	PMID[469058]

☑ 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 NPC475290 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	201
0.1-0.2	1301
0.2-0.3	4384
0.3-0.4	9821
0.4-0.5	11986
0.5-0.6	6211
0.6-0.7	6632
0.7-0.8	2054
0.8-0.85	87
0.85-0.9	4
0.9-0.95	0
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC475585
0.9897	High Similarity	NPC474550
0.9897	High Similarity	NPC473577
0.9694	High Similarity	NPC475331
0.9694	High Similarity	NPC288502
0.9694	High Similarity	NPC181104
0.9694	High Similarity	NPC121518
0.9694	High Similarity	NPC103298
0.9694	High Similarity	NPC201144
0.9694	High Similarity	NPC475335
0.9694	High Similarity	NPC80809
0.9596	High Similarity	NPC60315
0.9592	High Similarity	NPC473694
0.9592	High Similarity	NPC475334
0.9592	High Similarity	NPC475623
0.8835	High Similarity	NPC470980
0.8824	High Similarity	NPC474124
0.8725	High Similarity	NPC475344
0.8725	High Similarity	NPC476471
0.8627	High Similarity	NPC475617
0.8558	High Similarity	NPC473543
0.8544	High Similarity	NPC470972
0.8491	Intermediate Similarity	NPC88701
0.8462	Intermediate Similarity	NPC473523
0.8416	Intermediate Similarity	NPC475304
0.8411	Intermediate Similarity	NPC472216
0.8411	Intermediate Similarity	NPC173905
0.8411	Intermediate Similarity	NPC5475
0.8411	Intermediate Similarity	NPC284828
0.8365	Intermediate Similarity	NPC214714
0.8365	Intermediate Similarity	NPC200672
0.8364	Intermediate Similarity	NPC43213
0.8364	Intermediate Similarity	NPC216665
0.835	Intermediate Similarity	NPC473510
0.835	Intermediate Similarity	NPC230546
0.8333	Intermediate Similarity	NPC475033
0.8333	Intermediate Similarity	NPC475563
0.8333	Intermediate Similarity	NPC475134
0.8333	Intermediate Similarity	NPC254121
0.8333	Intermediate Similarity	NPC475032
0.8269	Intermediate Similarity	NPC155974
0.8269	Intermediate Similarity	NPC26557
0.8257	Intermediate Similarity	NPC470076
0.8257	Intermediate Similarity	NPC473921
0.8257	Intermediate Similarity	NPC475668
0.8257	Intermediate Similarity	NPC475480
0.8241	Intermediate Similarity	NPC40728
0.8235	Intermediate Similarity	NPC88009
0.8198	Intermediate Similarity	NPC178289
0.819	Intermediate Similarity	NPC472552
0.819	Intermediate Similarity	NPC252242
0.819	Intermediate Similarity	NPC475956
0.8173	Intermediate Similarity	NPC272223
0.8173	Intermediate Similarity	NPC208358
0.8165	Intermediate Similarity	NPC238850
0.8155	Intermediate Similarity	NPC274793
0.8155	Intermediate Similarity	NPC210337
0.8148	Intermediate Similarity	NPC472218
0.8148	Intermediate Similarity	NPC48548
0.8148	Intermediate Similarity	NPC128795
0.8148	Intermediate Similarity	NPC217921
0.8148	Intermediate Similarity	NPC472217
0.8148	Intermediate Similarity	NPC472219
0.8148	Intermediate Similarity	NPC135015
0.8137	Intermediate Similarity	NPC86893
0.8137	Intermediate Similarity	NPC292178
0.8131	Intermediate Similarity	NPC119855
0.8131	Intermediate Similarity	NPC220217
0.8131	Intermediate Similarity	NPC186668
0.8125	Intermediate Similarity	NPC470075
0.8113	Intermediate Similarity	NPC232515
0.8113	Intermediate Similarity	NPC474783
0.8113	Intermediate Similarity	NPC472821
0.8113	Intermediate Similarity	NPC260809
0.8113	Intermediate Similarity	NPC474775
0.8103	Intermediate Similarity	NPC129992
0.8095	Intermediate Similarity	NPC289670
0.8095	Intermediate Similarity	NPC472554
0.8077	Intermediate Similarity	NPC470067
0.8077	Intermediate Similarity	NPC470066
0.8077	Intermediate Similarity	NPC474957
0.8077	Intermediate Similarity	NPC79449
0.8073	Intermediate Similarity	NPC316974
0.807	Intermediate Similarity	NPC5883
0.807	Intermediate Similarity	NPC29639
0.807	Intermediate Similarity	NPC44899
0.807	Intermediate Similarity	NPC304260
0.807	Intermediate Similarity	NPC472667
0.8058	Intermediate Similarity	NPC253115
0.8058	Intermediate Similarity	NPC129569
0.8058	Intermediate Similarity	NPC221801
0.8058	Intermediate Similarity	NPC211810
0.8058	Intermediate Similarity	NPC284194
0.8058	Intermediate Similarity	NPC471765
0.8058	Intermediate Similarity	NPC304899
0.8056	Intermediate Similarity	NPC475781
0.8056	Intermediate Similarity	NPC473173
0.8056	Intermediate Similarity	NPC125423
0.8056	Intermediate Similarity	NPC473586
0.8056	Intermediate Similarity	NPC469318
0.8056	Intermediate Similarity	NPC88013
0.8053	Intermediate Similarity	NPC93883
0.8053	Intermediate Similarity	NPC203862
0.8039	Intermediate Similarity	NPC472360
0.8039	Intermediate Similarity	NPC473258
0.8039	Intermediate Similarity	NPC472416
0.8039	Intermediate Similarity	NPC105375
0.8039	Intermediate Similarity	NPC39453
0.8039	Intermediate Similarity	NPC474922
0.8039	Intermediate Similarity	NPC182826
0.8037	Intermediate Similarity	NPC152966
0.802	Intermediate Similarity	NPC234335
0.8019	Intermediate Similarity	NPC475986
0.8019	Intermediate Similarity	NPC474709
0.8019	Intermediate Similarity	NPC165578
0.8018	Intermediate Similarity	NPC470063
0.8017	Intermediate Similarity	NPC162009
0.8017	Intermediate Similarity	NPC257017
0.8	Intermediate Similarity	NPC38855
0.8	Intermediate Similarity	NPC472214
0.8	Intermediate Similarity	NPC246028
0.8	Intermediate Similarity	NPC181298
0.8	Intermediate Similarity	NPC79579
0.8	Intermediate Similarity	NPC472215
0.8	Intermediate Similarity	NPC251680
0.8	Intermediate Similarity	NPC274643
0.7982	Intermediate Similarity	NPC124676
0.7982	Intermediate Similarity	NPC311223
0.7982	Intermediate Similarity	NPC146280
0.7982	Intermediate Similarity	NPC475263
0.7982	Intermediate Similarity	NPC475372
0.7981	Intermediate Similarity	NPC347923
0.7981	Intermediate Similarity	NPC473244
0.7981	Intermediate Similarity	NPC476057
0.7965	Intermediate Similarity	NPC199428
0.7965	Intermediate Similarity	NPC106228
0.7965	Intermediate Similarity	NPC5311
0.7965	Intermediate Similarity	NPC193382
0.7965	Intermediate Similarity	NPC99620
0.7965	Intermediate Similarity	NPC138372
0.7965	Intermediate Similarity	NPC207637
0.7965	Intermediate Similarity	NPC310341
0.7963	Intermediate Similarity	NPC475414
0.7963	Intermediate Similarity	NPC173172
0.7961	Intermediate Similarity	NPC37603
0.7961	Intermediate Similarity	NPC476720
0.7961	Intermediate Similarity	NPC471786
0.7944	Intermediate Similarity	NPC196471
0.7944	Intermediate Similarity	NPC10232
0.7944	Intermediate Similarity	NPC189588
0.7944	Intermediate Similarity	NPC7644
0.7944	Intermediate Similarity	NPC475889
0.7944	Intermediate Similarity	NPC7613
0.7944	Intermediate Similarity	NPC127933
0.7944	Intermediate Similarity	NPC187302
0.7944	Intermediate Similarity	NPC85742
0.7944	Intermediate Similarity	NPC160583
0.7944	Intermediate Similarity	NPC97487
0.7941	Intermediate Similarity	NPC99653
0.7931	Intermediate Similarity	NPC52839
0.7931	Intermediate Similarity	NPC231518
0.7931	Intermediate Similarity	NPC475219
0.7928	Intermediate Similarity	NPC114188
0.7925	Intermediate Similarity	NPC268829
0.7925	Intermediate Similarity	NPC476132
0.7925	Intermediate Similarity	NPC25177
0.7925	Intermediate Similarity	NPC49532
0.7925	Intermediate Similarity	NPC247701
0.7925	Intermediate Similarity	NPC295110
0.7925	Intermediate Similarity	NPC222875
0.7925	Intermediate Similarity	NPC11974
0.7921	Intermediate Similarity	NPC470832
0.7913	Intermediate Similarity	NPC32177
0.7913	Intermediate Similarity	NPC19028
0.7913	Intermediate Similarity	NPC236973
0.7913	Intermediate Similarity	NPC469756
0.7913	Intermediate Similarity	NPC292467
0.7913	Intermediate Similarity	NPC278681
0.7913	Intermediate Similarity	NPC5292
0.7913	Intermediate Similarity	NPC475041
0.7913	Intermediate Similarity	NPC312536
0.7913	Intermediate Similarity	NPC470897
0.7913	Intermediate Similarity	NPC477071
0.7913	Intermediate Similarity	NPC30483
0.7913	Intermediate Similarity	NPC9674
0.7913	Intermediate Similarity	NPC469380
0.7913	Intermediate Similarity	NPC55532
0.7909	Intermediate Similarity	NPC42662
0.7909	Intermediate Similarity	NPC475274
0.7909	Intermediate Similarity	NPC218853
0.7905	Intermediate Similarity	NPC470068
0.7905	Intermediate Similarity	NPC102426
0.7905	Intermediate Similarity	NPC274458
0.7905	Intermediate Similarity	NPC300179
0.7895	Intermediate Similarity	NPC158344
0.7895	Intermediate Similarity	NPC10721
0.7895	Intermediate Similarity	NPC77319
0.7895	Intermediate Similarity	NPC87250
0.7895	Intermediate Similarity	NPC309034
0.7895	Intermediate Similarity	NPC27507

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 NPC475290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1652
0.2-0.3	3834
0.3-0.4	2316
0.4-0.5	695
0.5-0.6	241
0.6-0.7	213
0.7-0.8	29
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
0.8077	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.7931	Intermediate Similarity	NPD8033	Approved
0.7845	Intermediate Similarity	NPD8294	Approved
0.7845	Intermediate Similarity	NPD8377	Approved
0.7826	Intermediate Similarity	NPD7327	Approved
0.7826	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD8296	Approved
0.7778	Intermediate Similarity	NPD8380	Approved
0.7778	Intermediate Similarity	NPD8335	Approved
0.7778	Intermediate Similarity	NPD8379	Approved
0.7778	Intermediate Similarity	NPD8378	Approved
0.7759	Intermediate Similarity	NPD7516	Approved
0.7667	Intermediate Similarity	NPD7507	Approved
0.757	Intermediate Similarity	NPD4225	Approved
0.748	Intermediate Similarity	NPD7319	Approved
0.7479	Intermediate Similarity	NPD7503	Approved
0.7395	Intermediate Similarity	NPD6319	Approved
0.7391	Intermediate Similarity	NPD8297	Approved
0.7368	Intermediate Similarity	NPD6371	Approved
0.7364	Intermediate Similarity	NPD7632	Discontinued
0.7345	Intermediate Similarity	NPD6686	Approved
0.7328	Intermediate Similarity	NPD8133	Approved
0.7288	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD5344	Discontinued
0.7257	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6053	Discontinued
0.7238	Intermediate Similarity	NPD7838	Discovery
0.7238	Intermediate Similarity	NPD6698	Approved
0.7238	Intermediate Similarity	NPD46	Approved
0.7179	Intermediate Similarity	NPD4632	Approved
0.717	Intermediate Similarity	NPD7637	Suspended
0.7168	Intermediate Similarity	NPD5739	Approved
0.7168	Intermediate Similarity	NPD6675	Approved
0.7168	Intermediate Similarity	NPD6402	Approved
0.7168	Intermediate Similarity	NPD7128	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6372	Approved
0.7105	Intermediate Similarity	NPD6412	Phase 2
0.7103	Intermediate Similarity	NPD6399	Phase 3
0.7087	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7320	Approved
0.7043	Intermediate Similarity	NPD6881	Approved
0.7043	Intermediate Similarity	NPD6899	Approved
0.704	Intermediate Similarity	NPD8293	Discontinued
0.7016	Intermediate Similarity	NPD7492	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.6984	Remote Similarity	NPD7736	Approved
0.6981	Remote Similarity	NPD6051	Approved
0.6967	Remote Similarity	NPD6059	Approved
0.6967	Remote Similarity	NPD6054	Approved
0.696	Remote Similarity	NPD6616	Approved
0.6957	Remote Similarity	NPD5701	Approved
0.6957	Remote Similarity	NPD5697	Approved
0.6952	Remote Similarity	NPD7524	Approved
0.6952	Remote Similarity	NPD4250	Approved
0.6952	Remote Similarity	NPD4251	Approved
0.6949	Remote Similarity	NPD6882	Approved
0.6931	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD7290	Approved
0.6923	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7078	Approved
0.6875	Remote Similarity	NPD6648	Approved
0.687	Remote Similarity	NPD6008	Approved
0.6864	Remote Similarity	NPD6847	Approved
0.6864	Remote Similarity	NPD6617	Approved
0.6864	Remote Similarity	NPD6869	Approved
0.686	Remote Similarity	NPD6009	Approved
0.6857	Remote Similarity	NPD4249	Approved
0.6855	Remote Similarity	NPD6370	Approved
0.6852	Remote Similarity	NPD8035	Phase 2
0.6852	Remote Similarity	NPD8034	Phase 2
0.6852	Remote Similarity	NPD7983	Approved
0.6847	Remote Similarity	NPD6083	Phase 2
0.6847	Remote Similarity	NPD6084	Phase 2
0.6838	Remote Similarity	NPD6014	Approved
0.6838	Remote Similarity	NPD6012	Approved
0.6838	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7604	Phase 2
0.678	Remote Similarity	NPD4634	Approved
0.6774	Remote Similarity	NPD5983	Phase 2
0.6774	Remote Similarity	NPD6016	Approved
0.6774	Remote Similarity	NPD6015	Approved
0.6765	Remote Similarity	NPD4820	Approved
0.6765	Remote Similarity	NPD7525	Registered
0.6765	Remote Similarity	NPD4821	Approved
0.6765	Remote Similarity	NPD4822	Approved
0.6765	Remote Similarity	NPD4819	Approved
0.6752	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6011	Approved
0.6733	Remote Similarity	NPD4271	Approved
0.6733	Remote Similarity	NPD4268	Approved
0.6731	Remote Similarity	NPD5362	Discontinued
0.6731	Remote Similarity	NPD6695	Phase 3
0.6723	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5988	Approved
0.6696	Remote Similarity	NPD4755	Approved
0.6693	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4786	Approved
0.664	Remote Similarity	NPD8513	Phase 3
0.664	Remote Similarity	NPD8516	Approved
0.664	Remote Similarity	NPD8515	Approved
0.664	Remote Similarity	NPD8517	Approved
0.6637	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4202	Approved
0.6636	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7750	Discontinued
0.6609	Remote Similarity	NPD5211	Phase 2
0.6607	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5785	Approved
0.6604	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4700	Approved
0.6579	Remote Similarity	NPD5286	Approved
0.6579	Remote Similarity	NPD5285	Approved
0.6579	Remote Similarity	NPD4696	Approved
0.6577	Remote Similarity	NPD7748	Approved
0.6571	Remote Similarity	NPD5331	Approved
0.6571	Remote Similarity	NPD5332	Approved
0.6549	Remote Similarity	NPD7902	Approved
0.6542	Remote Similarity	NPD7334	Approved
0.6542	Remote Similarity	NPD6409	Approved
0.6542	Remote Similarity	NPD7521	Approved
0.6542	Remote Similarity	NPD6684	Approved
0.6542	Remote Similarity	NPD5330	Approved
0.6542	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD4790	Discontinued
0.6535	Remote Similarity	NPD6067	Discontinued
0.6535	Remote Similarity	NPD8328	Phase 3
0.6535	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4159	Approved
0.6514	Remote Similarity	NPD5328	Approved
0.6505	Remote Similarity	NPD6929	Approved
0.6504	Remote Similarity	NPD6274	Approved
0.6496	Remote Similarity	NPD5141	Approved
0.6491	Remote Similarity	NPD5696	Approved
0.6486	Remote Similarity	NPD5778	Approved
0.6486	Remote Similarity	NPD5779	Approved
0.648	Remote Similarity	NPD7100	Approved
0.648	Remote Similarity	NPD7101	Approved
0.6476	Remote Similarity	NPD3667	Approved
0.6476	Remote Similarity	NPD6435	Approved
0.6466	Remote Similarity	NPD5225	Approved
0.6466	Remote Similarity	NPD5224	Approved
0.6466	Remote Similarity	NPD4633	Approved
0.6466	Remote Similarity	NPD5226	Approved
0.6462	Remote Similarity	NPD6033	Approved
0.6442	Remote Similarity	NPD6931	Approved
0.6442	Remote Similarity	NPD6930	Phase 2
0.6441	Remote Similarity	NPD4768	Approved
0.6441	Remote Similarity	NPD4767	Approved
0.6436	Remote Similarity	NPD6942	Approved
0.6436	Remote Similarity	NPD7339	Approved
0.6422	Remote Similarity	NPD6903	Approved
0.6422	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7154	Phase 3
0.641	Remote Similarity	NPD5175	Approved
0.641	Remote Similarity	NPD5174	Approved
0.6408	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6335	Approved
0.6396	Remote Similarity	NPD6079	Approved
0.6396	Remote Similarity	NPD7515	Phase 2
0.6396	Remote Similarity	NPD5693	Phase 1
0.6389	Remote Similarity	NPD3618	Phase 1
0.6385	Remote Similarity	NPD8074	Phase 3
0.6379	Remote Similarity	NPD5223	Approved
0.6378	Remote Similarity	NPD6908	Approved
0.6378	Remote Similarity	NPD6909	Approved
0.6373	Remote Similarity	NPD6933	Approved
0.6372	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD1695	Approved
0.6355	Remote Similarity	NPD3133	Approved
0.6355	Remote Similarity	NPD3665	Phase 1
0.6355	Remote Similarity	NPD3666	Approved
0.6333	Remote Similarity	NPD4730	Approved
0.6333	Remote Similarity	NPD4729	Approved
0.6321	Remote Similarity	NPD4270	Approved
0.6321	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4269	Approved
0.632	Remote Similarity	NPD6317	Approved
0.6316	Remote Similarity	NPD7260	Phase 2
0.6311	Remote Similarity	NPD5776	Phase 2
0.6311	Remote Similarity	NPD6925	Approved
0.6286	Remote Similarity	NPD5368	Approved
0.6286	Remote Similarity	NPD7514	Phase 3
0.6283	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7900	Approved
0.6273	Remote Similarity	NPD6672	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