NPASS Compound

Structure

NPC474124 OpenBabel07101718182D 41 44 0 0 1 0 0 0 0 0999 V2000 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 2 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 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 1.5000 0.0000 C 0 0 1 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 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 -2.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 32 1 0 0 0 0 15 22 2 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 16 33 1 0 0 0 0 18 3 1 6 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 19 34 2 0 0 0 0 19 39 1 0 0 0 0 20 35 2 0 0 0 0 20 40 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 24 1 0 0 0 0 22 29 1 0 0 0 0 23 33 1 1 0 0 0 24 33 1 1 0 0 0 25 37 1 1 0 0 0 26 31 1 0 0 0 0 26 38 1 1 0 0 0 27 30 1 0 0 0 0 27 39 1 6 0 0 0 28 29 1 0 0 0 0 28 40 1 6 0 0 0 29 32 1 1 0 0 0 30 31 1 0 0 0 0 30 32 1 1 0 0 0 31 41 1 1 0 0 0 32 7 1 1 0 0 0 33 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.37
Volume:	604.874
LogP:	4.561
LogD:	4.324
LogS:	-4.079
# Rotatable Bonds:	11
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.236
Synthetic Accessibility Score:	5.331
Fsp3:	0.848
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:	-4.751
MDCK Permeability:	9.046230115927756e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.463
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	86.86241912841797%
Volume Distribution (VD):	1.861
Pgp-substrate:	3.568098306655884%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.397
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.456
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	2.406
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.957
Drug-inuced Liver Injury (DILI):	0.883
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.125
Carcinogencity:	0.013
Eye Corrosion:	0.012
Eye Irritation:	0.022
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC474124

Natural Product ID:	NPC474124
*Common Name:**	Agosterol G
IUPAC Name:	[(3S,4R,5S,6S,9R,10R,11R,13R,14R,17R)-4,6-diacetyloxy-3-hydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl] acetate
Synonyms:	Agosterol G
Standard InCHIKey:	CPBGNMKWCQJLLJ-GWDBHVHZSA-N
Standard InCHI:	InChI=1S/C33H52O8/c1-17(2)9-12-25(37)18(3)23-10-11-24-22-15-27(39-19(4)34)30-31(41-21(6)36)26(38)13-14-32(30,7)29(22)28(40-20(5)35)16-33(23,24)8/h15,17-18,23-31,37-38H,9-14,16H2,1-8H3/t18-,23+,24-,25+,26-,27-,28+,29+,30-,31-,32+,33+/m0/s1
SMILES:	CC(CC[C@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)C[C@@H](OC(=O)C)[C@H]1C2=C[C@@H]([C@@H]2[C@]1(C)CC[C@@H]([C@@H]2OC(=O)C)O)OC(=O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462502
PubChem CID:	10483263
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510593]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15568767]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257533]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834155]

☑ 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
IC50	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	8.8	ug.mL-1	PMID[558485]
NPT2	Others	Unspecified		IC50	=	100.0	ug.mL-1	PMID[558485]

☑ 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 NPC474124 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	200
0.1-0.2	1305
0.2-0.3	4211
0.3-0.4	8704
0.4-0.5	12275
0.5-0.6	6399
0.6-0.7	5528
0.7-0.8	3622
0.8-0.85	403
0.85-0.9	38
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC475344
0.9895	High Similarity	NPC476471
0.9789	High Similarity	NPC475617
0.9691	High Similarity	NPC473543
0.9588	High Similarity	NPC473523
0.9479	High Similarity	NPC230546
0.9479	High Similarity	NPC473510
0.9368	High Similarity	NPC88009
0.9271	High Similarity	NPC210337
0.9072	High Similarity	NPC475033
0.9072	High Similarity	NPC475032
0.899	High Similarity	NPC155974
0.8947	High Similarity	NPC234335
0.8932	High Similarity	NPC472216
0.8932	High Similarity	NPC5475
0.8932	High Similarity	NPC284828
0.8932	High Similarity	NPC173905
0.8922	High Similarity	NPC473586
0.8911	High Similarity	NPC475585
0.8911	High Similarity	NPC474550
0.8911	High Similarity	NPC473577
0.8889	High Similarity	NPC208358
0.8835	High Similarity	NPC475263
0.8835	High Similarity	NPC88701
0.8824	High Similarity	NPC475290
0.88	High Similarity	NPC472554
0.8788	High Similarity	NPC300179
0.8788	High Similarity	NPC102426
0.8776	High Similarity	NPC12103
0.8776	High Similarity	NPC276103
0.8776	High Similarity	NPC98457
0.8776	High Similarity	NPC54248
0.8776	High Similarity	NPC227583
0.8763	High Similarity	NPC474922
0.8725	High Similarity	NPC93352
0.8713	High Similarity	NPC472552
0.8687	High Similarity	NPC274793
0.8673	High Similarity	NPC8774
0.8667	High Similarity	NPC472215
0.8667	High Similarity	NPC472214
0.8654	High Similarity	NPC472219
0.8654	High Similarity	NPC472218
0.8654	High Similarity	NPC472217
0.8641	High Similarity	NPC88349
0.8627	High Similarity	NPC281378
0.8627	High Similarity	NPC473694
0.8627	High Similarity	NPC475334
0.8627	High Similarity	NPC475623
0.8614	High Similarity	NPC289670
0.8614	High Similarity	NPC96784
0.8614	High Similarity	NPC235920
0.8614	High Similarity	NPC11974
0.8614	High Similarity	NPC476132
0.8611	High Similarity	NPC207637
0.86	High Similarity	NPC470066
0.86	High Similarity	NPC247233
0.86	High Similarity	NPC470067
0.86	High Similarity	NPC470068
0.8586	High Similarity	NPC253115
0.8586	High Similarity	NPC288970
0.8586	High Similarity	NPC284194
0.8586	High Similarity	NPC221801
0.8586	High Similarity	NPC471765
0.8586	High Similarity	NPC304899
0.8586	High Similarity	NPC211810
0.8586	High Similarity	NPC129569
0.8586	High Similarity	NPC475178
0.8586	High Similarity	NPC72204
0.8586	High Similarity	NPC471903
0.8585	High Similarity	NPC470076
0.8571	High Similarity	NPC40728
0.8571	High Similarity	NPC105375
0.8571	High Similarity	NPC127718
0.8571	High Similarity	NPC472416
0.8571	High Similarity	NPC472360
0.8571	High Similarity	NPC182826
0.8571	High Similarity	NPC65402
0.8558	High Similarity	NPC475781
0.8558	High Similarity	NPC33053
0.8544	High Similarity	NPC85593
0.8544	High Similarity	NPC121518
0.8544	High Similarity	NPC201144
0.8544	High Similarity	NPC80809
0.8544	High Similarity	NPC152966
0.8544	High Similarity	NPC31430
0.8544	High Similarity	NPC75608
0.8544	High Similarity	NPC103298
0.8544	High Similarity	NPC288502
0.8544	High Similarity	NPC181104
0.8544	High Similarity	NPC475331
0.8544	High Similarity	NPC475335
0.8542	High Similarity	NPC246028
0.8532	High Similarity	NPC203862
0.8529	High Similarity	NPC470972
0.8529	High Similarity	NPC470053
0.8515	High Similarity	NPC476195
0.8515	High Similarity	NPC474190
0.8515	High Similarity	NPC38855
0.8515	High Similarity	NPC188968
0.85	High Similarity	NPC473244
0.8491	Intermediate Similarity	NPC177047
0.8491	Intermediate Similarity	NPC475563
0.8491	Intermediate Similarity	NPC475134
0.8476	Intermediate Similarity	NPC48548
0.8476	Intermediate Similarity	NPC135015
0.8476	Intermediate Similarity	NPC50124
0.8476	Intermediate Similarity	NPC128795
0.8476	Intermediate Similarity	NPC217921
0.8462	Intermediate Similarity	NPC220217
0.8462	Intermediate Similarity	NPC473199
0.8462	Intermediate Similarity	NPC60315
0.8462	Intermediate Similarity	NPC186668
0.8462	Intermediate Similarity	NPC119855
0.8447	Intermediate Similarity	NPC472821
0.844	Intermediate Similarity	NPC146652
0.844	Intermediate Similarity	NPC470075
0.8431	Intermediate Similarity	NPC470054
0.8431	Intermediate Similarity	NPC49532
0.8426	Intermediate Similarity	NPC144068
0.8421	Intermediate Similarity	NPC474970
0.8416	Intermediate Similarity	NPC477875
0.8416	Intermediate Similarity	NPC477876
0.8411	Intermediate Similarity	NPC475480
0.8411	Intermediate Similarity	NPC473921
0.8411	Intermediate Similarity	NPC263827
0.8411	Intermediate Similarity	NPC285410
0.8411	Intermediate Similarity	NPC250481
0.8411	Intermediate Similarity	NPC475668
0.8411	Intermediate Similarity	NPC114188
0.84	Intermediate Similarity	NPC306797
0.84	Intermediate Similarity	NPC169270
0.84	Intermediate Similarity	NPC292718
0.84	Intermediate Similarity	NPC111834
0.8396	Intermediate Similarity	NPC157530
0.8396	Intermediate Similarity	NPC250089
0.8396	Intermediate Similarity	NPC154085
0.8396	Intermediate Similarity	NPC296761
0.8396	Intermediate Similarity	NPC125361
0.8396	Intermediate Similarity	NPC43976
0.8396	Intermediate Similarity	NPC51925
0.8396	Intermediate Similarity	NPC472901
0.8396	Intermediate Similarity	NPC316974
0.8396	Intermediate Similarity	NPC14630
0.8381	Intermediate Similarity	NPC88013
0.8381	Intermediate Similarity	NPC471205
0.8381	Intermediate Similarity	NPC125423
0.8381	Intermediate Similarity	NPC234160
0.8381	Intermediate Similarity	NPC472390
0.8378	Intermediate Similarity	NPC477071
0.8378	Intermediate Similarity	NPC304260
0.8378	Intermediate Similarity	NPC44899
0.8378	Intermediate Similarity	NPC5883
0.8378	Intermediate Similarity	NPC29639
0.8367	Intermediate Similarity	NPC177641
0.8367	Intermediate Similarity	NPC219516
0.8367	Intermediate Similarity	NPC210268
0.8365	Intermediate Similarity	NPC470768
0.8364	Intermediate Similarity	NPC93883
0.8364	Intermediate Similarity	NPC152615
0.8351	Intermediate Similarity	NPC261320
0.8351	Intermediate Similarity	NPC473647
0.835	Intermediate Similarity	NPC177701
0.835	Intermediate Similarity	NPC283343
0.835	Intermediate Similarity	NPC273668
0.835	Intermediate Similarity	NPC154452
0.835	Intermediate Similarity	NPC258547
0.835	Intermediate Similarity	NPC11956
0.8333	Intermediate Similarity	NPC79303
0.8333	Intermediate Similarity	NPC477972
0.8333	Intermediate Similarity	NPC20113
0.8333	Intermediate Similarity	NPC228251
0.8333	Intermediate Similarity	NPC328074
0.8333	Intermediate Similarity	NPC321272
0.8333	Intermediate Similarity	NPC167974
0.8333	Intermediate Similarity	NPC477971
0.8333	Intermediate Similarity	NPC254567
0.8333	Intermediate Similarity	NPC317460
0.8333	Intermediate Similarity	NPC477968
0.8333	Intermediate Similarity	NPC161527
0.8333	Intermediate Similarity	NPC219285
0.8333	Intermediate Similarity	NPC271295
0.8333	Intermediate Similarity	NPC470063
0.8333	Intermediate Similarity	NPC474571
0.8333	Intermediate Similarity	NPC470025
0.8318	Intermediate Similarity	NPC103627
0.8318	Intermediate Similarity	NPC191439
0.8318	Intermediate Similarity	NPC316708
0.8318	Intermediate Similarity	NPC170974
0.8304	Intermediate Similarity	NPC107607
0.8302	Intermediate Similarity	NPC38217
0.8302	Intermediate Similarity	NPC295980
0.8302	Intermediate Similarity	NPC258323
0.8302	Intermediate Similarity	NPC311223
0.8302	Intermediate Similarity	NPC472988
0.83	Intermediate Similarity	NPC241047
0.83	Intermediate Similarity	NPC276110
0.8288	Intermediate Similarity	NPC218093
0.8288	Intermediate Similarity	NPC160888
0.8288	Intermediate Similarity	NPC475403
0.8286	Intermediate Similarity	NPC470056

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 NPC474124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1488
0.2-0.3	3828
0.3-0.4	2393
0.4-0.5	742
0.5-0.6	257
0.6-0.7	202
0.7-0.8	71
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD7638	Approved
0.823	Intermediate Similarity	NPD8033	Approved
0.8214	Intermediate Similarity	NPD7516	Approved
0.8155	Intermediate Similarity	NPD7639	Approved
0.8155	Intermediate Similarity	NPD7640	Approved
0.8142	Intermediate Similarity	NPD8377	Approved
0.8142	Intermediate Similarity	NPD8294	Approved
0.8125	Intermediate Similarity	NPD7328	Approved
0.8125	Intermediate Similarity	NPD7327	Approved
0.807	Intermediate Similarity	NPD8380	Approved
0.807	Intermediate Similarity	NPD8378	Approved
0.807	Intermediate Similarity	NPD8379	Approved
0.807	Intermediate Similarity	NPD8335	Approved
0.807	Intermediate Similarity	NPD8296	Approved
0.7913	Intermediate Similarity	NPD7503	Approved
0.7727	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7115	Discovery
0.7714	Intermediate Similarity	NPD4225	Approved
0.7647	Intermediate Similarity	NPD7507	Approved
0.7636	Intermediate Similarity	NPD6686	Approved
0.76	Intermediate Similarity	NPD7524	Approved
0.7573	Intermediate Similarity	NPD6399	Phase 3
0.757	Intermediate Similarity	NPD5344	Discontinued
0.7522	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7632	Discontinued
0.7459	Intermediate Similarity	NPD7319	Approved
0.7456	Intermediate Similarity	NPD8133	Approved
0.7451	Intermediate Similarity	NPD6051	Approved
0.7423	Intermediate Similarity	NPD7525	Registered
0.7411	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6319	Approved
0.7308	Intermediate Similarity	NPD7637	Suspended
0.7304	Intermediate Similarity	NPD4632	Approved
0.73	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6675	Approved
0.7297	Intermediate Similarity	NPD5739	Approved
0.7297	Intermediate Similarity	NPD6402	Approved
0.7297	Intermediate Similarity	NPD7128	Approved
0.7263	Intermediate Similarity	NPD7339	Approved
0.7263	Intermediate Similarity	NPD6942	Approved
0.7257	Intermediate Similarity	NPD6372	Approved
0.7257	Intermediate Similarity	NPD6373	Approved
0.7232	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6412	Phase 2
0.7212	Intermediate Similarity	NPD7838	Discovery
0.72	Intermediate Similarity	NPD6695	Phase 3
0.7168	Intermediate Similarity	NPD6899	Approved
0.7168	Intermediate Similarity	NPD6881	Approved
0.7168	Intermediate Similarity	NPD7320	Approved
0.7168	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6648	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.713	Intermediate Similarity	NPD8130	Phase 1
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.7129	Intermediate Similarity	NPD4786	Approved
0.7091	Intermediate Similarity	NPD4159	Approved
0.7087	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7750	Discontinued
0.708	Intermediate Similarity	NPD5697	Approved
0.708	Intermediate Similarity	NPD5701	Approved
0.7069	Intermediate Similarity	NPD6053	Discontinued
0.7069	Intermediate Similarity	NPD6882	Approved
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
0.7016	Intermediate Similarity	NPD8293	Discontinued
0.701	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7748	Approved
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
0.6975	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6009	Approved
0.6972	Remote Similarity	NPD6083	Phase 2
0.6972	Remote Similarity	NPD6084	Phase 2
0.6972	Remote Similarity	NPD7902	Approved
0.697	Remote Similarity	NPD6929	Approved
0.697	Remote Similarity	NPD7645	Phase 2
0.696	Remote Similarity	NPD7736	Approved
0.6957	Remote Similarity	NPD6013	Approved
0.6957	Remote Similarity	NPD6012	Approved
0.6957	Remote Similarity	NPD6014	Approved
0.6952	Remote Similarity	NPD5328	Approved
0.6942	Remote Similarity	NPD6054	Approved
0.6942	Remote Similarity	NPD6059	Approved
0.6935	Remote Similarity	NPD6616	Approved
0.6931	Remote Similarity	NPD3667	Approved
0.6911	Remote Similarity	NPD8328	Phase 3
0.6911	Remote Similarity	NPD7604	Phase 2
0.69	Remote Similarity	NPD6931	Approved
0.69	Remote Similarity	NPD6930	Phase 2
0.6893	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8516	Approved
0.6885	Remote Similarity	NPD5983	Phase 2
0.6885	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD8515	Approved
0.6885	Remote Similarity	NPD8517	Approved
0.688	Remote Similarity	NPD7078	Approved
0.687	Remote Similarity	NPD6011	Approved
0.6838	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6933	Approved
0.6829	Remote Similarity	NPD6370	Approved
0.6827	Remote Similarity	NPD3618	Phase 1
0.6822	Remote Similarity	NPD6079	Approved
0.6822	Remote Similarity	NPD7515	Phase 2
0.6818	Remote Similarity	NPD4755	Approved
0.68	Remote Similarity	NPD6336	Discontinued
0.6768	Remote Similarity	NPD6925	Approved
0.6768	Remote Similarity	NPD5776	Phase 2
0.6759	Remote Similarity	NPD4202	Approved
0.6752	Remote Similarity	NPD4634	Approved
0.6748	Remote Similarity	NPD6016	Approved
0.6748	Remote Similarity	NPD6015	Approved
0.6733	Remote Similarity	NPD7514	Phase 3
0.6726	Remote Similarity	NPD5211	Phase 2
0.67	Remote Similarity	NPD7145	Approved
0.6698	Remote Similarity	NPD5737	Approved
0.6698	Remote Similarity	NPD6672	Approved
0.6697	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7900	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
0.6695	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6902	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6638	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5695	Phase 3
0.6635	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6924	Approved
0.6633	Remote Similarity	NPD6926	Approved
0.6614	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD6921	Approved
0.6612	Remote Similarity	NPD6274	Approved
0.661	Remote Similarity	NPD6371	Approved
0.6609	Remote Similarity	NPD5141	Approved
0.6607	Remote Similarity	NPD5696	Approved
0.6607	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.66	Remote Similarity	NPD6932	Approved
0.6594	Remote Similarity	NPD7625	Phase 1
0.6585	Remote Similarity	NPD7100	Approved
0.6585	Remote Similarity	NPD7101	Approved
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	NPD5220	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5222	Approved
0.6577	Remote Similarity	NPD4697	Phase 3
0.6577	Remote Similarity	NPD5221	Approved
0.6571	Remote Similarity	NPD6893	Approved
0.6571	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7332	Phase 2
0.6552	Remote Similarity	NPD4767	Approved
0.6552	Remote Similarity	NPD4768	Approved
0.6552	Remote Similarity	NPD6640	Phase 3
0.6542	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6903	Approved
0.6538	Remote Similarity	NPD7260	Phase 2
0.6535	Remote Similarity	NPD6118	Approved
0.6535	Remote Similarity	NPD6115	Approved
0.6535	Remote Similarity	NPD6114	Approved
0.6535	Remote Similarity	NPD6697	Approved
0.6522	Remote Similarity	NPD5174	Approved
0.6522	Remote Similarity	NPD5175	Approved
0.6518	Remote Similarity	NPD5173	Approved
0.6514	Remote Similarity	NPD6411	Approved
0.6514	Remote Similarity	NPD5693	Phase 1
0.6508	Remote Similarity	NPD6067	Discontinued
0.6504	Remote Similarity	NPD6335	Approved
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	NPD3668	Phase 3
0.6476	Remote Similarity	NPD3666	Approved
0.6476	Remote Similarity	NPD3665	Phase 1
0.6475	Remote Similarity	NPD6868	Approved
0.6471	Remote Similarity	NPD6683	Phase 2
0.6465	Remote Similarity	NPD4784	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