NPASS Compound

Structure

NPC475331 OpenBabel07101718192D 47 49 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 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 -2.8019 -4.2535 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 3.3175 -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 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 -5.1011 -2.0338 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 -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 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 -3.9227 -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 -3.9800 -2.9838 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 1.3612 -1.2330 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 -2.2914 -2.5984 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 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 19 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 18 35 1 0 0 0 0 20 30 1 0 0 0 0 21 37 2 0 0 0 0 21 43 1 0 0 0 0 22 38 2 0 0 0 0 22 44 1 0 0 0 0 23 29 1 0 0 0 0 23 35 1 6 0 0 0 24 36 1 1 0 0 0 24 45 1 0 0 0 0 25 39 2 0 0 0 0 25 45 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 19 1 1 0 0 0 28 29 1 0 0 0 0 28 31 1 0 0 0 0 29 36 1 1 0 0 0 30 32 1 0 0 0 0 30 42 1 1 0 0 0 31 34 1 0 0 0 0 31 46 1 1 0 0 0 32 33 1 0 0 0 0 32 43 1 1 0 0 0 33 35 1 6 0 0 0 33 44 1 0 0 0 0 34 36 1 6 0 0 0 34 47 1 0 0 0 0 35 9 1 6 0 0 0 36 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	664.38
Volume:	686.416
LogP:	4.898
LogD:	4.096
LogS:	-4.824
# Rotatable Bonds:	17
TPSA:	151.73
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	5.392
Fsp3:	0.806
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:	-4.859
MDCK Permeability:	8.59639112604782e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.797
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	85.49890899658203%
Volume Distribution (VD):	0.832
Pgp-substrate:	3.7559385299682617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.019
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.716
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.755
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	7.025
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.16
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.219
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.346

Download Data

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

Natural Product: NPC475331

Natural Product ID:	NPC475331
*Common Name:**	Gagunin P
IUPAC Name:	[(1R,2R,3R,3aR,4S,5aR,6S,7S,8S,10aR,10bS)-6,7-diacetyloxy-2,3-di(butanoyloxy)-8-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 P
Standard InCHIKey:	DZNCDWMYHUXBQE-QHZQYIMRSA-N
Standard InCHI:	InChI=1S/C36H56O11/c1-11-14-25(39)45-24-18-35(9)23(17-20(6)30(42)32(43-21(7)37)33(35)44-22(8)38)29-28(19(4)5)31(46-26(40)15-12-2)34(36(24,29)10)47-27(41)16-13-3/h17,19,23-24,28-34,42H,11-16,18H2,1-10H3/t23-,24+,28-,29+,30+,31-,32+,33-,34+,35-,36+/m1/s1
SMILES:	CCCC(=O)OC1CC2(C(C=C(C(C(C2OC(=O)C)OC(=O)C)O)C)C3C1(C(C(C3C(C)C)OC(=O)CCC)OC(=O)CCC)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503610
PubChem CID:	25135938
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	=	8.5	ug.mL-1	PMID[569045]
NPT2	Others	Unspecified		LC50	=	55.0	ug.mL-1	PMID[569045]

☑ 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 NPC475331 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	191
0.1-0.2	1271
0.2-0.3	4396
0.3-0.4	10662
0.4-0.5	11348
0.5-0.6	6241
0.6-0.7	6620
0.7-0.8	1893
0.8-0.85	59
0.85-0.9	0
0.9-0.95	0
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475335
1.0	High Similarity	NPC80809
1.0	High Similarity	NPC181104
1.0	High Similarity	NPC201144
1.0	High Similarity	NPC103298
1.0	High Similarity	NPC288502
1.0	High Similarity	NPC121518
0.9897	High Similarity	NPC60315
0.9896	High Similarity	NPC475623
0.9896	High Similarity	NPC475334
0.9896	High Similarity	NPC473694
0.9694	High Similarity	NPC475290
0.9592	High Similarity	NPC473577
0.9592	High Similarity	NPC475585
0.9592	High Similarity	NPC474550
0.8558	High Similarity	NPC470980
0.8544	High Similarity	NPC474124
0.8462	Intermediate Similarity	NPC473543
0.8447	Intermediate Similarity	NPC476471
0.8447	Intermediate Similarity	NPC475344
0.8416	Intermediate Similarity	NPC475032
0.8416	Intermediate Similarity	NPC475033
0.84	Intermediate Similarity	NPC86893
0.84	Intermediate Similarity	NPC292178
0.8396	Intermediate Similarity	NPC472218
0.8396	Intermediate Similarity	NPC472217
0.8396	Intermediate Similarity	NPC88701
0.8396	Intermediate Similarity	NPC472219
0.8365	Intermediate Similarity	NPC473523
0.835	Intermediate Similarity	NPC155974
0.835	Intermediate Similarity	NPC475617
0.83	Intermediate Similarity	NPC473258
0.83	Intermediate Similarity	NPC474922
0.8286	Intermediate Similarity	NPC152966
0.8273	Intermediate Similarity	NPC43213
0.8273	Intermediate Similarity	NPC216665
0.8269	Intermediate Similarity	NPC470972
0.8252	Intermediate Similarity	NPC208358
0.8235	Intermediate Similarity	NPC254121
0.819	Intermediate Similarity	NPC85742
0.8173	Intermediate Similarity	NPC289670
0.8165	Intermediate Similarity	NPC475480
0.8165	Intermediate Similarity	NPC475668
0.8165	Intermediate Similarity	NPC473921
0.8155	Intermediate Similarity	NPC470066
0.8155	Intermediate Similarity	NPC470067
0.8148	Intermediate Similarity	NPC173905
0.8148	Intermediate Similarity	NPC5475
0.8148	Intermediate Similarity	NPC472216
0.8148	Intermediate Similarity	NPC284828
0.8144	Intermediate Similarity	NPC477668
0.8137	Intermediate Similarity	NPC304899
0.8137	Intermediate Similarity	NPC292718
0.8137	Intermediate Similarity	NPC475304
0.8137	Intermediate Similarity	NPC253115
0.8137	Intermediate Similarity	NPC111834
0.8137	Intermediate Similarity	NPC169270
0.8137	Intermediate Similarity	NPC276103
0.8137	Intermediate Similarity	NPC306797
0.8137	Intermediate Similarity	NPC54248
0.8119	Intermediate Similarity	NPC39453
0.8095	Intermediate Similarity	NPC214714
0.8095	Intermediate Similarity	NPC200672
0.8077	Intermediate Similarity	NPC272223
0.8077	Intermediate Similarity	NPC230546
0.8077	Intermediate Similarity	NPC475877
0.8077	Intermediate Similarity	NPC473510
0.8073	Intermediate Similarity	NPC475563
0.8073	Intermediate Similarity	NPC238850
0.8073	Intermediate Similarity	NPC475134
0.8039	Intermediate Similarity	NPC241047
0.8036	Intermediate Similarity	NPC470075
0.8018	Intermediate Similarity	NPC250109
0.8018	Intermediate Similarity	NPC962
0.8	Intermediate Similarity	NPC476132
0.8	Intermediate Similarity	NPC26557
0.8	Intermediate Similarity	NPC114188
0.8	Intermediate Similarity	NPC48732
0.8	Intermediate Similarity	NPC470076
0.8	Intermediate Similarity	NPC470832
0.7982	Intermediate Similarity	NPC5989
0.7982	Intermediate Similarity	NPC275696
0.7982	Intermediate Similarity	NPC40728
0.7982	Intermediate Similarity	NPC5991
0.7982	Intermediate Similarity	NPC218853
0.7982	Intermediate Similarity	NPC22628
0.7982	Intermediate Similarity	NPC255081
0.7982	Intermediate Similarity	NPC471108
0.7981	Intermediate Similarity	NPC102426
0.7981	Intermediate Similarity	NPC470068
0.7981	Intermediate Similarity	NPC300179
0.7963	Intermediate Similarity	NPC475781
0.7961	Intermediate Similarity	NPC475178
0.7961	Intermediate Similarity	NPC211810
0.7961	Intermediate Similarity	NPC221801
0.7961	Intermediate Similarity	NPC284194
0.7961	Intermediate Similarity	NPC471765
0.7961	Intermediate Similarity	NPC88009
0.7946	Intermediate Similarity	NPC472400
0.7946	Intermediate Similarity	NPC178289
0.7946	Intermediate Similarity	NPC220293
0.7944	Intermediate Similarity	NPC470768
0.7944	Intermediate Similarity	NPC75608
0.7941	Intermediate Similarity	NPC472360
0.7941	Intermediate Similarity	NPC472416
0.7928	Intermediate Similarity	NPC280782
0.7928	Intermediate Similarity	NPC477050
0.7925	Intermediate Similarity	NPC252242
0.7925	Intermediate Similarity	NPC470053
0.7925	Intermediate Similarity	NPC472552
0.7925	Intermediate Similarity	NPC165578
0.7925	Intermediate Similarity	NPC475956
0.7909	Intermediate Similarity	NPC181298
0.7909	Intermediate Similarity	NPC250956
0.7909	Intermediate Similarity	NPC129340
0.7909	Intermediate Similarity	NPC6206
0.7905	Intermediate Similarity	NPC167974
0.7905	Intermediate Similarity	NPC251680
0.7905	Intermediate Similarity	NPC476195
0.7905	Intermediate Similarity	NPC38855
0.79	Intermediate Similarity	NPC246028
0.7895	Intermediate Similarity	NPC472758
0.7895	Intermediate Similarity	NPC471125
0.7895	Intermediate Similarity	NPC171905
0.7895	Intermediate Similarity	NPC472397
0.7895	Intermediate Similarity	NPC472080
0.789	Intermediate Similarity	NPC128795
0.789	Intermediate Similarity	NPC217921
0.789	Intermediate Similarity	NPC135015
0.789	Intermediate Similarity	NPC48548
0.789	Intermediate Similarity	NPC295980
0.789	Intermediate Similarity	NPC258323
0.7885	Intermediate Similarity	NPC473244
0.7885	Intermediate Similarity	NPC210337
0.7885	Intermediate Similarity	NPC274793
0.7876	Intermediate Similarity	NPC266728
0.7876	Intermediate Similarity	NPC49492
0.7876	Intermediate Similarity	NPC146652
0.787	Intermediate Similarity	NPC231530
0.787	Intermediate Similarity	NPC119855
0.787	Intermediate Similarity	NPC220217
0.787	Intermediate Similarity	NPC472898
0.787	Intermediate Similarity	NPC472899
0.787	Intermediate Similarity	NPC278628
0.787	Intermediate Similarity	NPC470056
0.787	Intermediate Similarity	NPC473199
0.787	Intermediate Similarity	NPC186668
0.787	Intermediate Similarity	NPC470055
0.787	Intermediate Similarity	NPC472900
0.7864	Intermediate Similarity	NPC476720
0.7863	Intermediate Similarity	NPC129992
0.7857	Intermediate Similarity	NPC472757
0.7857	Intermediate Similarity	NPC251309
0.7857	Intermediate Similarity	NPC144068
0.785	Intermediate Similarity	NPC472821
0.785	Intermediate Similarity	NPC218513
0.785	Intermediate Similarity	NPC471467
0.785	Intermediate Similarity	NPC55954
0.785	Intermediate Similarity	NPC232515
0.785	Intermediate Similarity	NPC474775
0.785	Intermediate Similarity	NPC474783
0.785	Intermediate Similarity	NPC473198
0.785	Intermediate Similarity	NPC222153
0.785	Intermediate Similarity	NPC260809
0.7845	Intermediate Similarity	NPC202051
0.7845	Intermediate Similarity	NPC52839
0.7843	Intermediate Similarity	NPC473678
0.7843	Intermediate Similarity	NPC99653
0.7843	Intermediate Similarity	NPC26046
0.7838	Intermediate Similarity	NPC285410
0.7838	Intermediate Similarity	NPC250481
0.7838	Intermediate Similarity	NPC470748
0.7838	Intermediate Similarity	NPC263827
0.7835	Intermediate Similarity	NPC477667
0.783	Intermediate Similarity	NPC470054
0.783	Intermediate Similarity	NPC96784
0.783	Intermediate Similarity	NPC235920
0.783	Intermediate Similarity	NPC472554
0.783	Intermediate Similarity	NPC144486
0.7826	Intermediate Similarity	NPC29639
0.7826	Intermediate Similarity	NPC44899
0.7826	Intermediate Similarity	NPC304260
0.7826	Intermediate Similarity	NPC5883
0.7826	Intermediate Similarity	NPC472667
0.7826	Intermediate Similarity	NPC475041
0.7822	Intermediate Similarity	NPC194485
0.7822	Intermediate Similarity	NPC471378
0.7822	Intermediate Similarity	NPC53890
0.7822	Intermediate Similarity	NPC312471
0.7822	Intermediate Similarity	NPC219937
0.7822	Intermediate Similarity	NPC123252
0.7818	Intermediate Similarity	NPC475274
0.7818	Intermediate Similarity	NPC170221
0.7818	Intermediate Similarity	NPC265655
0.7818	Intermediate Similarity	NPC316974
0.7818	Intermediate Similarity	NPC10064
0.781	Intermediate Similarity	NPC274458
0.781	Intermediate Similarity	NPC119036
0.781	Intermediate Similarity	NPC476895
0.781	Intermediate Similarity	NPC469725

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 NPC475331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1654
0.2-0.3	3906
0.3-0.4	2310
0.4-0.5	641
0.5-0.6	228
0.6-0.7	221
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
0.7905	Intermediate Similarity	NPD7640	Approved
0.7905	Intermediate Similarity	NPD7639	Approved
0.781	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD8033	Approved
0.7607	Intermediate Similarity	NPD8294	Approved
0.7607	Intermediate Similarity	NPD8377	Approved
0.7586	Intermediate Similarity	NPD7328	Approved
0.7586	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD8296	Approved
0.7542	Intermediate Similarity	NPD8335	Approved
0.7542	Intermediate Similarity	NPD8380	Approved
0.7542	Intermediate Similarity	NPD8379	Approved
0.7542	Intermediate Similarity	NPD8378	Approved
0.7521	Intermediate Similarity	NPD7516	Approved
0.7477	Intermediate Similarity	NPD4225	Approved
0.7458	Intermediate Similarity	NPD6319	Approved
0.7456	Intermediate Similarity	NPD8297	Approved
0.7438	Intermediate Similarity	NPD7507	Approved
0.7404	Intermediate Similarity	NPD7637	Suspended
0.7281	Intermediate Similarity	NPD6371	Approved
0.7273	Intermediate Similarity	NPD7632	Discontinued
0.7258	Intermediate Similarity	NPD7319	Approved
0.725	Intermediate Similarity	NPD7503	Approved
0.7241	Intermediate Similarity	NPD4632	Approved
0.7232	Intermediate Similarity	NPD5739	Approved
0.7232	Intermediate Similarity	NPD7128	Approved
0.7232	Intermediate Similarity	NPD6402	Approved
0.7232	Intermediate Similarity	NPD6675	Approved
0.7203	Intermediate Similarity	NPD7115	Discovery
0.7193	Intermediate Similarity	NPD6372	Approved
0.7193	Intermediate Similarity	NPD6373	Approved
0.7184	Intermediate Similarity	NPD4251	Approved
0.7184	Intermediate Similarity	NPD4250	Approved
0.7184	Intermediate Similarity	NPD7524	Approved
0.7182	Intermediate Similarity	NPD5344	Discontinued
0.7172	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6399	Phase 3
0.7168	Intermediate Similarity	NPD6412	Phase 2
0.7105	Intermediate Similarity	NPD6881	Approved
0.7105	Intermediate Similarity	NPD7320	Approved
0.7105	Intermediate Similarity	NPD6686	Approved
0.7105	Intermediate Similarity	NPD6899	Approved
0.7097	Intermediate Similarity	NPD8293	Discontinued
0.7094	Intermediate Similarity	NPD8133	Approved
0.7087	Intermediate Similarity	NPD4249	Approved
0.7075	Intermediate Similarity	NPD7983	Approved
0.7073	Intermediate Similarity	NPD7492	Approved
0.7069	Intermediate Similarity	NPD6649	Approved
0.7069	Intermediate Similarity	NPD8130	Phase 1
0.7069	Intermediate Similarity	NPD6650	Approved
0.7059	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7736	Approved
0.7025	Intermediate Similarity	NPD6054	Approved
0.7025	Intermediate Similarity	NPD6059	Approved
0.7018	Intermediate Similarity	NPD5701	Approved
0.7018	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5697	Approved
0.7016	Intermediate Similarity	NPD6616	Approved
0.7009	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD4821	Approved
0.7	Intermediate Similarity	NPD4819	Approved
0.7	Intermediate Similarity	NPD4822	Approved
0.7	Intermediate Similarity	NPD4820	Approved
0.6983	Remote Similarity	NPD7290	Approved
0.6983	Remote Similarity	NPD6883	Approved
0.6983	Remote Similarity	NPD7102	Approved
0.6981	Remote Similarity	NPD7838	Discovery
0.6981	Remote Similarity	NPD46	Approved
0.6981	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD4271	Approved
0.697	Remote Similarity	NPD4268	Approved
0.6961	Remote Similarity	NPD5362	Discontinued
0.6961	Remote Similarity	NPD6695	Phase 3
0.696	Remote Similarity	NPD7078	Approved
0.693	Remote Similarity	NPD6008	Approved
0.6923	Remote Similarity	NPD6869	Approved
0.6923	Remote Similarity	NPD6847	Approved
0.6923	Remote Similarity	NPD6617	Approved
0.6917	Remote Similarity	NPD6009	Approved
0.6916	Remote Similarity	NPD8034	Phase 2
0.6916	Remote Similarity	NPD8035	Phase 2
0.6911	Remote Similarity	NPD6370	Approved
0.6909	Remote Similarity	NPD6083	Phase 2
0.6909	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD6013	Approved
0.6897	Remote Similarity	NPD6014	Approved
0.6897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6012	Approved
0.6897	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7750	Discontinued
0.6857	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7604	Phase 2
0.6838	Remote Similarity	NPD4634	Approved
0.6832	Remote Similarity	NPD7525	Registered
0.6829	Remote Similarity	NPD6016	Approved
0.6829	Remote Similarity	NPD6015	Approved
0.6829	Remote Similarity	NPD5983	Phase 2
0.6827	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5211	Phase 2
0.681	Remote Similarity	NPD6011	Approved
0.6796	Remote Similarity	NPD5332	Approved
0.6796	Remote Similarity	NPD5331	Approved
0.6786	Remote Similarity	NPD6648	Approved
0.678	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5988	Approved
0.6765	Remote Similarity	NPD4790	Discontinued
0.6757	Remote Similarity	NPD4755	Approved
0.6746	Remote Similarity	NPD6336	Discontinued
0.6733	Remote Similarity	NPD6929	Approved
0.6731	Remote Similarity	NPD4786	Approved
0.6729	Remote Similarity	NPD6051	Approved
0.6727	Remote Similarity	NPD5695	Phase 3
0.6697	Remote Similarity	NPD4202	Approved
0.6697	Remote Similarity	NPD5779	Approved
0.6697	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6695	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD6931	Approved
0.6639	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4696	Approved
0.6637	Remote Similarity	NPD5285	Approved
0.6637	Remote Similarity	NPD5286	Approved
0.6637	Remote Similarity	NPD4700	Approved
0.6636	Remote Similarity	NPD7748	Approved
0.6635	Remote Similarity	NPD7154	Phase 3
0.6634	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7902	Approved
0.6604	Remote Similarity	NPD7334	Approved
0.6604	Remote Similarity	NPD6409	Approved
0.6604	Remote Similarity	NPD5330	Approved
0.6604	Remote Similarity	NPD7521	Approved
0.6604	Remote Similarity	NPD7146	Approved
0.6604	Remote Similarity	NPD6684	Approved
0.66	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6067	Discontinued
0.6587	Remote Similarity	NPD8328	Phase 3
0.6574	Remote Similarity	NPD5328	Approved
0.656	Remote Similarity	NPD8513	Phase 3
0.656	Remote Similarity	NPD8515	Approved
0.656	Remote Similarity	NPD8517	Approved
0.656	Remote Similarity	NPD8516	Approved
0.6557	Remote Similarity	NPD6274	Approved
0.6549	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5696	Approved
0.6538	Remote Similarity	NPD4269	Approved
0.6538	Remote Similarity	NPD4270	Approved
0.6538	Remote Similarity	NPD3667	Approved
0.6538	Remote Similarity	NPD6435	Approved
0.6535	Remote Similarity	NPD5776	Phase 2
0.6535	Remote Similarity	NPD6925	Approved
0.6532	Remote Similarity	NPD7100	Approved
0.6532	Remote Similarity	NPD7101	Approved
0.6525	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5225	Approved
0.6522	Remote Similarity	NPD4633	Approved
0.6522	Remote Similarity	NPD5224	Approved
0.6522	Remote Similarity	NPD5226	Approved
0.6518	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5785	Approved
0.6512	Remote Similarity	NPD6033	Approved
0.6505	Remote Similarity	NPD7514	Phase 3
0.65	Remote Similarity	NPD6942	Approved
0.65	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7339	Approved
0.6496	Remote Similarity	NPD4768	Approved
0.6496	Remote Similarity	NPD4767	Approved
0.6481	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6903	Approved
0.6471	Remote Similarity	NPD7145	Approved
0.6466	Remote Similarity	NPD5175	Approved
0.6466	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD7515	Phase 2
0.6455	Remote Similarity	NPD7087	Discontinued
0.6455	Remote Similarity	NPD6079	Approved
0.6452	Remote Similarity	NPD6335	Approved
0.6449	Remote Similarity	NPD5786	Approved
0.6449	Remote Similarity	NPD3618	Phase 1
0.6442	Remote Similarity	NPD6902	Approved
0.6441	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6933	Approved
0.6435	Remote Similarity	NPD5223	Approved
0.6429	Remote Similarity	NPD6908	Approved
0.6429	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6909	Approved
0.6422	Remote Similarity	NPD4753	Phase 2
0.6415	Remote Similarity	NPD3666	Approved
0.6415	Remote Similarity	NPD3665	Phase 1
0.6415	Remote Similarity	NPD3133	Approved
0.6387	Remote Similarity	NPD4729	Approved
0.6387	Remote Similarity	NPD4730	Approved
0.6371	Remote Similarity	NPD6317	Approved
0.6355	Remote Similarity	NPD5363	Approved
0.6355	Remote Similarity	NPD6893	Approved
0.6346	Remote Similarity	NPD7332	Phase 2
0.6346	Remote Similarity	NPD5368	Approved
0.6346	Remote Similarity	NPD4252	Approved
0.6339	Remote Similarity	NPD7900	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