NPASS Compound

Structure

NPC473694 OpenBabel07101719122D 41 43 0 0 1 0 0 0 0 0999 V2000 -5.5685 3.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5804 -4.9086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5733 3.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7138 4.1723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3802 2.1828 0.0000 C 0 0 0 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 3.7344 -0.1029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8029 -3.9337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0698 -3.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 1.6691 0.0000 C 0 0 0 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 -0.4048 3.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7568 1.4010 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 3.3691 -1.0338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 1 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 -3.5685 3.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2924 -2.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 2.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1906 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7568 -0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7818 -0.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 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 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9926 -1.8156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0685 4.3147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2479 -1.9838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1906 0.5000 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 2.3802 -1.1828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5685 3.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5593 -1.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 15 32 1 0 0 0 0 16 23 1 0 0 0 0 16 31 1 0 0 0 0 18 28 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 34 2 0 0 0 0 20 39 1 0 0 0 0 21 27 1 0 0 0 0 21 31 1 1 0 0 0 22 26 1 0 0 0 0 22 40 1 6 0 0 0 23 32 1 6 0 0 0 23 38 1 0 0 0 0 24 35 2 0 0 0 0 24 40 1 0 0 0 0 25 36 2 0 0 0 0 25 41 1 0 0 0 0 26 17 1 6 0 0 0 26 27 1 0 0 0 0 27 32 1 6 0 0 0 28 29 1 0 0 0 0 28 37 1 6 0 0 0 29 30 1 0 0 0 0 29 39 1 6 0 0 0 30 31 1 1 0 0 0 30 41 1 0 0 0 0 31 8 1 1 0 0 0 32 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.35
Volume:	602.288
LogP:	4.892
LogD:	4.144
LogS:	-4.367
# Rotatable Bonds:	13
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.23
Synthetic Accessibility Score:	5.223
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
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:	-4.858
MDCK Permeability:	5.368319762055762e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.585
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	85.5051498413086%
Volume Distribution (VD):	1.337
Pgp-substrate:	4.6520819664001465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.345
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.352
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.413

ADMET: Excretion

Clearance (CL):	7.524
Half-life (T1/2):	0.538

ADMET: Toxicity

hERG Blockers:	0.186
Human Hepatotoxicity (H-HT):	0.72
Drug-inuced Liver Injury (DILI):	0.88
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.301
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.605
Carcinogencity:	0.053
Eye Corrosion:	0.007
Eye Irritation:	0.019
Respiratory Toxicity:	0.777

Download Data

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

Natural Product: NPC473694

Natural Product ID:	NPC473694
*Common Name:**	Gagunin L
IUPAC Name:	[(1R,2S,3aR,4S,5aR,6S,7S,8S,10aR,10bS)-4,7-diacetyloxy-6-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] butanoate
Synonyms:	Gagunin L
Standard InCHIKey:	DAINGSDYCXGCHD-AQEUHLRASA-N
Standard InCHI:	InChI=1S/C32H50O9/c1-10-12-24(35)40-22-15-32(9)23(38-19(6)33)16-31(8)21(27(32)26(22)17(3)4)14-18(5)28(37)29(39-20(7)34)30(31)41-25(36)13-11-2/h14,17,21-23,26-30,37H,10-13,15-16H2,1-9H3/t21-,22+,23+,26+,27+,28+,29+,30-,31-,32+/m1/s1
SMILES:	CCCC(=O)O[C@H]1C[C@@]2([C@H]([C@H]1C(C)C)[C@H]1C=C(C)[C@@H]([C@@H]([C@H]([C@@]1(C[C@@H]2OC(=O)C)C)OC(=O)CCC)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449338
PubChem CID:	25135936
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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	=	12.5	ug.mL-1	PMID[570089]
NPT2	Others	Unspecified		LC50	=	55.0	ug.mL-1	PMID[570089]

☑ 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 NPC473694 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	189
0.1-0.2	1242
0.2-0.3	4327
0.3-0.4	10238
0.4-0.5	11638
0.5-0.6	6114
0.6-0.7	6757
0.7-0.8	2106
0.8-0.85	67
0.85-0.9	3
0.9-0.95	0
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475623
1.0	High Similarity	NPC475334
0.9896	High Similarity	NPC103298
0.9896	High Similarity	NPC80809
0.9896	High Similarity	NPC181104
0.9896	High Similarity	NPC475331
0.9896	High Similarity	NPC121518
0.9896	High Similarity	NPC475335
0.9896	High Similarity	NPC201144
0.9896	High Similarity	NPC288502
0.9794	High Similarity	NPC60315
0.9691	High Similarity	NPC475585
0.9691	High Similarity	NPC473577
0.9691	High Similarity	NPC474550
0.9592	High Similarity	NPC475290
0.8627	High Similarity	NPC474124
0.8544	High Similarity	NPC473543
0.8529	High Similarity	NPC475344
0.8529	High Similarity	NPC476471
0.85	High Similarity	NPC475032
0.85	High Similarity	NPC475033
0.8485	Intermediate Similarity	NPC86893
0.8485	Intermediate Similarity	NPC292178
0.8476	Intermediate Similarity	NPC472219
0.8476	Intermediate Similarity	NPC472217
0.8476	Intermediate Similarity	NPC88701
0.8476	Intermediate Similarity	NPC472218
0.8462	Intermediate Similarity	NPC470980
0.8447	Intermediate Similarity	NPC473523
0.8431	Intermediate Similarity	NPC475617
0.8431	Intermediate Similarity	NPC155974
0.8384	Intermediate Similarity	NPC473258
0.8384	Intermediate Similarity	NPC474922
0.8365	Intermediate Similarity	NPC152966
0.835	Intermediate Similarity	NPC470972
0.8349	Intermediate Similarity	NPC216665
0.8349	Intermediate Similarity	NPC43213
0.8333	Intermediate Similarity	NPC208358
0.8317	Intermediate Similarity	NPC254121
0.8269	Intermediate Similarity	NPC85742
0.8252	Intermediate Similarity	NPC289670
0.8241	Intermediate Similarity	NPC475668
0.8241	Intermediate Similarity	NPC475480
0.8241	Intermediate Similarity	NPC473921
0.8235	Intermediate Similarity	NPC470067
0.8235	Intermediate Similarity	NPC470066
0.8229	Intermediate Similarity	NPC477668
0.8224	Intermediate Similarity	NPC284828
0.8224	Intermediate Similarity	NPC5475
0.8224	Intermediate Similarity	NPC472216
0.8224	Intermediate Similarity	NPC173905
0.8218	Intermediate Similarity	NPC292718
0.8218	Intermediate Similarity	NPC306797
0.8218	Intermediate Similarity	NPC276103
0.8218	Intermediate Similarity	NPC304899
0.8218	Intermediate Similarity	NPC253115
0.8218	Intermediate Similarity	NPC475304
0.8218	Intermediate Similarity	NPC54248
0.8218	Intermediate Similarity	NPC169270
0.8218	Intermediate Similarity	NPC111834
0.8155	Intermediate Similarity	NPC272223
0.8155	Intermediate Similarity	NPC230546
0.8155	Intermediate Similarity	NPC475877
0.8155	Intermediate Similarity	NPC473510
0.8148	Intermediate Similarity	NPC238850
0.8148	Intermediate Similarity	NPC475563
0.8148	Intermediate Similarity	NPC475134
0.8119	Intermediate Similarity	NPC241047
0.8108	Intermediate Similarity	NPC470075
0.8091	Intermediate Similarity	NPC250109
0.8091	Intermediate Similarity	NPC962
0.8081	Intermediate Similarity	NPC470832
0.8081	Intermediate Similarity	NPC48732
0.8077	Intermediate Similarity	NPC476132
0.8073	Intermediate Similarity	NPC114188
0.8073	Intermediate Similarity	NPC470076
0.8058	Intermediate Similarity	NPC470068
0.8058	Intermediate Similarity	NPC300179
0.8058	Intermediate Similarity	NPC102426
0.8056	Intermediate Similarity	NPC40728
0.8056	Intermediate Similarity	NPC218853
0.8053	Intermediate Similarity	NPC275696
0.8053	Intermediate Similarity	NPC471108
0.8053	Intermediate Similarity	NPC22628
0.8053	Intermediate Similarity	NPC255081
0.8053	Intermediate Similarity	NPC5991
0.8053	Intermediate Similarity	NPC5989
0.8039	Intermediate Similarity	NPC221801
0.8039	Intermediate Similarity	NPC88009
0.8039	Intermediate Similarity	NPC284194
0.8039	Intermediate Similarity	NPC211810
0.8039	Intermediate Similarity	NPC471765
0.8039	Intermediate Similarity	NPC475178
0.8037	Intermediate Similarity	NPC475781
0.802	Intermediate Similarity	NPC39453
0.802	Intermediate Similarity	NPC472416
0.802	Intermediate Similarity	NPC472360
0.8019	Intermediate Similarity	NPC75608
0.8019	Intermediate Similarity	NPC470768
0.8018	Intermediate Similarity	NPC220293
0.8018	Intermediate Similarity	NPC178289
0.8018	Intermediate Similarity	NPC472400
0.8	Intermediate Similarity	NPC470053
0.8	Intermediate Similarity	NPC472552
0.8	Intermediate Similarity	NPC165578
0.8	Intermediate Similarity	NPC200672
0.8	Intermediate Similarity	NPC280782
0.8	Intermediate Similarity	NPC214714
0.7982	Intermediate Similarity	NPC250956
0.7982	Intermediate Similarity	NPC129340
0.7982	Intermediate Similarity	NPC181298
0.7981	Intermediate Similarity	NPC251680
0.7981	Intermediate Similarity	NPC38855
0.7981	Intermediate Similarity	NPC167974
0.7981	Intermediate Similarity	NPC476195
0.798	Intermediate Similarity	NPC246028
0.7965	Intermediate Similarity	NPC472080
0.7965	Intermediate Similarity	NPC472397
0.7965	Intermediate Similarity	NPC171905
0.7965	Intermediate Similarity	NPC472758
0.7965	Intermediate Similarity	NPC471125
0.7963	Intermediate Similarity	NPC128795
0.7963	Intermediate Similarity	NPC217921
0.7963	Intermediate Similarity	NPC135015
0.7963	Intermediate Similarity	NPC48548
0.7963	Intermediate Similarity	NPC295980
0.7963	Intermediate Similarity	NPC258323
0.7961	Intermediate Similarity	NPC473244
0.7961	Intermediate Similarity	NPC274793
0.7961	Intermediate Similarity	NPC210337
0.7946	Intermediate Similarity	NPC146652
0.7946	Intermediate Similarity	NPC266728
0.7946	Intermediate Similarity	NPC49492
0.7944	Intermediate Similarity	NPC220217
0.7944	Intermediate Similarity	NPC278628
0.7944	Intermediate Similarity	NPC119855
0.7944	Intermediate Similarity	NPC470055
0.7944	Intermediate Similarity	NPC473199
0.7944	Intermediate Similarity	NPC472898
0.7944	Intermediate Similarity	NPC472899
0.7944	Intermediate Similarity	NPC472900
0.7944	Intermediate Similarity	NPC470056
0.7944	Intermediate Similarity	NPC231530
0.7941	Intermediate Similarity	NPC476720
0.7931	Intermediate Similarity	NPC129992
0.7928	Intermediate Similarity	NPC144068
0.7928	Intermediate Similarity	NPC472757
0.7928	Intermediate Similarity	NPC251309
0.7925	Intermediate Similarity	NPC474775
0.7925	Intermediate Similarity	NPC471467
0.7925	Intermediate Similarity	NPC218513
0.7925	Intermediate Similarity	NPC222153
0.7925	Intermediate Similarity	NPC472821
0.7925	Intermediate Similarity	NPC473198
0.7925	Intermediate Similarity	NPC55954
0.7921	Intermediate Similarity	NPC26046
0.7921	Intermediate Similarity	NPC473678
0.7921	Intermediate Similarity	NPC99653
0.7917	Intermediate Similarity	NPC477667
0.7913	Intermediate Similarity	NPC52839
0.7913	Intermediate Similarity	NPC202051
0.7909	Intermediate Similarity	NPC285410
0.7909	Intermediate Similarity	NPC250481
0.7909	Intermediate Similarity	NPC263827
0.7905	Intermediate Similarity	NPC472554
0.7905	Intermediate Similarity	NPC235920
0.7905	Intermediate Similarity	NPC470054
0.7905	Intermediate Similarity	NPC26557
0.7905	Intermediate Similarity	NPC144486
0.7905	Intermediate Similarity	NPC96784
0.79	Intermediate Similarity	NPC312471
0.79	Intermediate Similarity	NPC123252
0.79	Intermediate Similarity	NPC219937
0.79	Intermediate Similarity	NPC194485
0.79	Intermediate Similarity	NPC53890
0.79	Intermediate Similarity	NPC471378
0.7895	Intermediate Similarity	NPC44899
0.7895	Intermediate Similarity	NPC304260
0.7895	Intermediate Similarity	NPC472667
0.7895	Intermediate Similarity	NPC5883
0.7895	Intermediate Similarity	NPC475041
0.7895	Intermediate Similarity	NPC29639
0.789	Intermediate Similarity	NPC265655
0.789	Intermediate Similarity	NPC475274
0.789	Intermediate Similarity	NPC316974
0.7885	Intermediate Similarity	NPC119036
0.7885	Intermediate Similarity	NPC247233
0.7885	Intermediate Similarity	NPC469725
0.7885	Intermediate Similarity	NPC476895
0.7879	Intermediate Similarity	NPC160304
0.7879	Intermediate Similarity	NPC470613
0.7879	Intermediate Similarity	NPC92370
0.7879	Intermediate Similarity	NPC470612
0.7876	Intermediate Similarity	NPC203862
0.7876	Intermediate Similarity	NPC156252
0.7876	Intermediate Similarity	NPC10721
0.7876	Intermediate Similarity	NPC93883
0.7876	Intermediate Similarity	NPC470171
0.787	Intermediate Similarity	NPC473586
0.787	Intermediate Similarity	NPC88013

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 NPC473694 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1629
0.2-0.3	3878
0.3-0.4	2337
0.4-0.5	661
0.5-0.6	226
0.6-0.7	225
0.7-0.8	37
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
0.7981	Intermediate Similarity	NPD7640	Approved
0.7981	Intermediate Similarity	NPD7639	Approved
0.7885	Intermediate Similarity	NPD7638	Approved
0.7759	Intermediate Similarity	NPD8033	Approved
0.7672	Intermediate Similarity	NPD8294	Approved
0.7672	Intermediate Similarity	NPD8377	Approved
0.7652	Intermediate Similarity	NPD7328	Approved
0.7652	Intermediate Similarity	NPD7327	Approved
0.7607	Intermediate Similarity	NPD8380	Approved
0.7607	Intermediate Similarity	NPD8335	Approved
0.7607	Intermediate Similarity	NPD8379	Approved
0.7607	Intermediate Similarity	NPD8378	Approved
0.7607	Intermediate Similarity	NPD8296	Approved
0.7586	Intermediate Similarity	NPD7516	Approved
0.7547	Intermediate Similarity	NPD4225	Approved
0.7522	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD7507	Approved
0.7476	Intermediate Similarity	NPD7637	Suspended
0.7373	Intermediate Similarity	NPD6319	Approved
0.7345	Intermediate Similarity	NPD6371	Approved
0.7339	Intermediate Similarity	NPD7632	Discontinued
0.7317	Intermediate Similarity	NPD7319	Approved
0.7311	Intermediate Similarity	NPD7503	Approved
0.7304	Intermediate Similarity	NPD4632	Approved
0.7297	Intermediate Similarity	NPD7128	Approved
0.7297	Intermediate Similarity	NPD6675	Approved
0.7297	Intermediate Similarity	NPD5739	Approved
0.7297	Intermediate Similarity	NPD6402	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7257	Intermediate Similarity	NPD6372	Approved
0.7257	Intermediate Similarity	NPD6373	Approved
0.7255	Intermediate Similarity	NPD7524	Approved
0.7255	Intermediate Similarity	NPD4250	Approved
0.7255	Intermediate Similarity	NPD4251	Approved
0.7248	Intermediate Similarity	NPD5344	Discontinued
0.7245	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6399	Phase 3
0.7232	Intermediate Similarity	NPD6412	Phase 2
0.7168	Intermediate Similarity	NPD6899	Approved
0.7168	Intermediate Similarity	NPD6686	Approved
0.7168	Intermediate Similarity	NPD6881	Approved
0.7168	Intermediate Similarity	NPD7320	Approved
0.7157	Intermediate Similarity	NPD4249	Approved
0.7155	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD7983	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD8130	Phase 1
0.713	Intermediate Similarity	NPD6650	Approved
0.7129	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5697	Approved
0.708	Intermediate Similarity	NPD5701	Approved
0.708	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4821	Approved
0.7071	Intermediate Similarity	NPD4820	Approved
0.7071	Intermediate Similarity	NPD4819	Approved
0.7071	Intermediate Similarity	NPD4822	Approved
0.7069	Intermediate Similarity	NPD6053	Discontinued
0.7069	Intermediate Similarity	NPD6882	Approved
0.7048	Intermediate Similarity	NPD7838	Discovery
0.7048	Intermediate Similarity	NPD6698	Approved
0.7048	Intermediate Similarity	NPD46	Approved
0.7043	Intermediate Similarity	NPD7290	Approved
0.7043	Intermediate Similarity	NPD7102	Approved
0.7043	Intermediate Similarity	NPD6883	Approved
0.7041	Intermediate Similarity	NPD4268	Approved
0.7041	Intermediate Similarity	NPD4271	Approved
0.703	Intermediate Similarity	NPD5362	Discontinued
0.703	Intermediate Similarity	NPD6695	Phase 3
0.7016	Intermediate Similarity	NPD8293	Discontinued
0.6992	Remote Similarity	NPD7492	Approved
0.6991	Remote Similarity	NPD6008	Approved
0.6983	Remote Similarity	NPD6617	Approved
0.6983	Remote Similarity	NPD6847	Approved
0.6983	Remote Similarity	NPD6869	Approved
0.6981	Remote Similarity	NPD8035	Phase 2
0.6981	Remote Similarity	NPD8034	Phase 2
0.6975	Remote Similarity	NPD6009	Approved
0.6972	Remote Similarity	NPD6084	Phase 2
0.6972	Remote Similarity	NPD6083	Phase 2
0.696	Remote Similarity	NPD7736	Approved
0.6957	Remote Similarity	NPD6013	Approved
0.6957	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6012	Approved
0.6957	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6014	Approved
0.6942	Remote Similarity	NPD6054	Approved
0.6942	Remote Similarity	NPD6059	Approved
0.6935	Remote Similarity	NPD6616	Approved
0.6923	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7750	Discontinued
0.6911	Remote Similarity	NPD7604	Phase 2
0.69	Remote Similarity	NPD7525	Registered
0.6893	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5983	Phase 2
0.688	Remote Similarity	NPD7078	Approved
0.6875	Remote Similarity	NPD5211	Phase 2
0.687	Remote Similarity	NPD6011	Approved
0.6863	Remote Similarity	NPD5332	Approved
0.6863	Remote Similarity	NPD5331	Approved
0.6847	Remote Similarity	NPD6648	Approved
0.6838	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4790	Discontinued
0.6829	Remote Similarity	NPD6370	Approved
0.6818	Remote Similarity	NPD4755	Approved
0.68	Remote Similarity	NPD6929	Approved
0.68	Remote Similarity	NPD6336	Discontinued
0.6796	Remote Similarity	NPD4786	Approved
0.6792	Remote Similarity	NPD6051	Approved
0.6789	Remote Similarity	NPD5695	Phase 3
0.6759	Remote Similarity	NPD5779	Approved
0.6759	Remote Similarity	NPD4202	Approved
0.6759	Remote Similarity	NPD5778	Approved
0.6754	Remote Similarity	NPD5141	Approved
0.6752	Remote Similarity	NPD4634	Approved
0.6752	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6016	Approved
0.6748	Remote Similarity	NPD6015	Approved
0.6733	Remote Similarity	NPD6930	Phase 2
0.6733	Remote Similarity	NPD6931	Approved
0.6731	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7154	Phase 3
0.6697	Remote Similarity	NPD7748	Approved
0.6696	Remote Similarity	NPD5286	Approved
0.6696	Remote Similarity	NPD5285	Approved
0.6696	Remote Similarity	NPD4700	Approved
0.6696	Remote Similarity	NPD4696	Approved
0.6694	Remote Similarity	NPD5988	Approved
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.664	Remote Similarity	NPD8328	Phase 3
0.6636	Remote Similarity	NPD5328	Approved
0.6613	Remote Similarity	NPD8517	Approved
0.6613	Remote Similarity	NPD8515	Approved
0.6613	Remote Similarity	NPD8516	Approved
0.6613	Remote Similarity	NPD8513	Phase 3
0.6612	Remote Similarity	NPD6274	Approved
0.6607	Remote Similarity	NPD5696	Approved
0.6607	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6435	Approved
0.6602	Remote Similarity	NPD4270	Approved
0.6602	Remote Similarity	NPD3667	Approved
0.6602	Remote Similarity	NPD4269	Approved
0.66	Remote Similarity	NPD6925	Approved
0.66	Remote Similarity	NPD5776	Phase 2
0.6585	Remote Similarity	NPD7100	Approved
0.6585	Remote Similarity	NPD7101	Approved
0.6581	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5226	Approved
0.6579	Remote Similarity	NPD5225	Approved
0.6579	Remote Similarity	NPD4633	Approved
0.6579	Remote Similarity	NPD5224	Approved
0.6577	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5785	Approved
0.6569	Remote Similarity	NPD7514	Phase 3
0.6566	Remote Similarity	NPD7339	Approved
0.6566	Remote Similarity	NPD6942	Approved
0.6555	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4767	Approved
0.6552	Remote Similarity	NPD4768	Approved
0.6542	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6903	Approved
0.6535	Remote Similarity	NPD7145	Approved
0.6522	Remote Similarity	NPD5174	Approved
0.6522	Remote Similarity	NPD5175	Approved
0.6514	Remote Similarity	NPD7087	Discontinued
0.6514	Remote Similarity	NPD6079	Approved
0.6514	Remote Similarity	NPD7515	Phase 2
0.6509	Remote Similarity	NPD3618	Phase 1
0.6509	Remote Similarity	NPD5786	Approved
0.6508	Remote Similarity	NPD6067	Discontinued
0.6505	Remote Similarity	NPD6902	Approved
0.6504	Remote Similarity	NPD6335	Approved
0.65	Remote Similarity	NPD6933	Approved
0.6496	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5223	Approved
0.6486	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4753	Phase 2
0.648	Remote Similarity	NPD6909	Approved
0.648	Remote Similarity	NPD6908	Approved
0.6476	Remote Similarity	NPD3133	Approved
0.6476	Remote Similarity	NPD3666	Approved
0.6476	Remote Similarity	NPD3665	Phase 1
0.6441	Remote Similarity	NPD4730	Approved
0.6441	Remote Similarity	NPD4729	Approved
0.6434	Remote Similarity	NPD6033	Approved
0.6423	Remote Similarity	NPD6317	Approved
0.6415	Remote Similarity	NPD6893	Approved
0.6415	Remote Similarity	NPD5363	Approved
0.6408	Remote Similarity	NPD7332	Phase 2
0.6408	Remote Similarity	NPD5368	Approved
0.6408	Remote Similarity	NPD4252	Approved
0.6396	Remote Similarity	NPD7901	Clinical (unspecified phase)

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