NPASS Compound

Structure

NPC230546 OpenBabel07101719512D 41 44 0 0 1 0 0 0 0 0999 V2000 6.8437 -0.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5565 0.4204 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9071 -3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1964 -1.2738 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 4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 -2.2248 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 -1.7321 -0.0000 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 -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 5.8655 -0.5306 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 1.7321 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 2.5981 -0.5000 0.0000 C 0 0 1 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 -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 3.5491 -1.8090 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 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 2.5981 -1.5000 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 3.8581 -2.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 -3.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6502 -3.7382 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 31 1 0 0 0 0 16 32 1 0 0 0 0 17 22 2 0 0 0 0 17 26 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 23 1 0 0 0 0 22 24 1 0 0 0 0 23 31 1 6 0 0 0 24 32 1 6 0 0 0 25 30 1 0 0 0 0 25 39 1 6 0 0 0 26 29 1 0 0 0 0 26 40 1 1 0 0 0 27 31 1 6 0 0 0 27 33 1 0 0 0 0 28 33 1 0 0 0 0 28 37 1 1 0 0 0 29 30 1 0 0 0 0 29 32 1 6 0 0 0 30 41 1 6 0 0 0 31 6 1 6 0 0 0 32 7 1 6 0 0 0 33 8 1 1 0 0 0 33 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.37
Volume:	604.874
LogP:	5.1
LogD:	4.006
LogS:	-4.917
# 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:	0.232
Synthetic Accessibility Score:	5.228
Fsp3:	0.848
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:	-4.666
MDCK Permeability:	8.167889609467238e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.465
Human Intestinal Absorption (HIA):	0.431
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	86.64266204833984%
Volume Distribution (VD):	1.819
Pgp-substrate:	4.053158283233643%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.23
CYP2C9-inhibitor:	0.166
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	2.978
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.583
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.803
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.866
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.319
Carcinogencity:	0.023
Eye Corrosion:	0.016
Eye Irritation:	0.028
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC230546

Natural Product ID:	NPC230546
*Common Name:**	Agosterol D2
IUPAC Name:	[(3S,4R,5S,6S,9R,10R,13S,14R,17S)-4,6-diacetyloxy-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:	Agosterol D2
Standard InCHIKey:	VAWRLWFOBLNLGU-WKNBELCHSA-N
Standard InCHI:	InChI=1S/C33H52O8/c1-18(2)9-12-28(37)33(8,38)27-11-10-23-22-17-26(40-20(4)35)29-30(41-21(5)36)25(39-19(3)34)14-16-32(29,7)24(22)13-15-31(23,27)6/h17-18,23-30,37-38H,9-16H2,1-8H3/t23-,24-,25-,26-,27-,28+,29-,30-,31-,32+,33+/m0/s1
SMILES:	CC(C)CC[C@H]([C@@](C)([C@H]1CC[C@H]2C3=C[C@@H]([C@H]4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC(=O)C)OC(=O)C)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503869
PubChem CID:	21632162
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	=	23.0	ug.mL-1	PMID[538611]
NPT2	Others	Unspecified		IC50	=	90.0	ug.mL-1	PMID[538611]

☑ 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 NPC230546 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	192
0.1-0.2	1273
0.2-0.3	4354
0.3-0.4	11046
0.4-0.5	10710
0.5-0.6	5979
0.6-0.7	5771
0.7-0.8	3119
0.8-0.85	221
0.85-0.9	22
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9785	High Similarity	NPC473510
0.9783	High Similarity	NPC210337
0.9674	High Similarity	NPC88009
0.9479	High Similarity	NPC474124
0.9479	High Similarity	NPC473523
0.9381	High Similarity	NPC473543
0.9375	High Similarity	NPC475344
0.9375	High Similarity	NPC476471
0.9271	High Similarity	NPC475617
0.8824	High Similarity	NPC284828
0.8824	High Similarity	NPC173905
0.8824	High Similarity	NPC5475
0.8824	High Similarity	NPC472216
0.866	High Similarity	NPC227583
0.866	High Similarity	NPC12103
0.866	High Similarity	NPC98457
0.8632	High Similarity	NPC177641
0.86	High Similarity	NPC258547
0.86	High Similarity	NPC283343
0.8586	High Similarity	NPC474190
0.8571	High Similarity	NPC475032
0.8571	High Similarity	NPC475033
0.8557	High Similarity	NPC8774
0.8544	High Similarity	NPC88701
0.8542	High Similarity	NPC27918
0.8526	High Similarity	NPC473269
0.85	High Similarity	NPC472554
0.85	High Similarity	NPC155974
0.85	High Similarity	NPC473160
0.85	High Similarity	NPC11974
0.8495	Intermediate Similarity	NPC474970
0.8485	Intermediate Similarity	NPC102426
0.8485	Intermediate Similarity	NPC300179
0.8469	Intermediate Similarity	NPC288970
0.8469	Intermediate Similarity	NPC471903
0.8454	Intermediate Similarity	NPC127718
0.8454	Intermediate Similarity	NPC65402
0.8447	Intermediate Similarity	NPC131665
0.8447	Intermediate Similarity	NPC255387
0.8447	Intermediate Similarity	NPC473586
0.8438	Intermediate Similarity	NPC234335
0.8431	Intermediate Similarity	NPC474550
0.8431	Intermediate Similarity	NPC475585
0.8431	Intermediate Similarity	NPC31430
0.8431	Intermediate Similarity	NPC473577
0.8431	Intermediate Similarity	NPC85593
0.8421	Intermediate Similarity	NPC473647
0.8416	Intermediate Similarity	NPC273668
0.8416	Intermediate Similarity	NPC472552
0.8404	Intermediate Similarity	NPC166857
0.84	Intermediate Similarity	NPC208358
0.84	Intermediate Similarity	NPC38855
0.8384	Intermediate Similarity	NPC231751
0.8384	Intermediate Similarity	NPC274793
0.8381	Intermediate Similarity	NPC472215
0.8381	Intermediate Similarity	NPC472214
0.8365	Intermediate Similarity	NPC472217
0.8365	Intermediate Similarity	NPC472219
0.8365	Intermediate Similarity	NPC475263
0.8365	Intermediate Similarity	NPC472218
0.8351	Intermediate Similarity	NPC38232
0.8351	Intermediate Similarity	NPC53555
0.835	Intermediate Similarity	NPC475290
0.835	Intermediate Similarity	NPC186668
0.835	Intermediate Similarity	NPC88349
0.835	Intermediate Similarity	NPC475414
0.835	Intermediate Similarity	NPC473199
0.835	Intermediate Similarity	NPC173172
0.8333	Intermediate Similarity	NPC472821
0.8333	Intermediate Similarity	NPC281378
0.8317	Intermediate Similarity	NPC235920
0.8317	Intermediate Similarity	NPC49532
0.8317	Intermediate Similarity	NPC96784
0.8317	Intermediate Similarity	NPC289670
0.8302	Intermediate Similarity	NPC470076
0.83	Intermediate Similarity	NPC477876
0.83	Intermediate Similarity	NPC470066
0.83	Intermediate Similarity	NPC477875
0.83	Intermediate Similarity	NPC470067
0.83	Intermediate Similarity	NPC470068
0.8298	Intermediate Similarity	NPC125399
0.8286	Intermediate Similarity	NPC51925
0.8286	Intermediate Similarity	NPC125361
0.8286	Intermediate Similarity	NPC154085
0.8286	Intermediate Similarity	NPC296761
0.8286	Intermediate Similarity	NPC43976
0.8283	Intermediate Similarity	NPC129569
0.8283	Intermediate Similarity	NPC72204
0.8283	Intermediate Similarity	NPC54248
0.8283	Intermediate Similarity	NPC276103
0.828	Intermediate Similarity	NPC470077
0.8269	Intermediate Similarity	NPC471205
0.8269	Intermediate Similarity	NPC33053
0.8269	Intermediate Similarity	NPC475176
0.8269	Intermediate Similarity	NPC475781
0.8265	Intermediate Similarity	NPC215700
0.8265	Intermediate Similarity	NPC474922
0.8261	Intermediate Similarity	NPC30166
0.8261	Intermediate Similarity	NPC470049
0.8257	Intermediate Similarity	NPC203862
0.8257	Intermediate Similarity	NPC93883
0.8257	Intermediate Similarity	NPC152615
0.8252	Intermediate Similarity	NPC93352
0.8247	Intermediate Similarity	NPC219516
0.8247	Intermediate Similarity	NPC189520
0.8247	Intermediate Similarity	NPC210268
0.8235	Intermediate Similarity	NPC470053
0.8235	Intermediate Similarity	NPC470972
0.8235	Intermediate Similarity	NPC473928
0.8229	Intermediate Similarity	NPC82876
0.8229	Intermediate Similarity	NPC20946
0.8218	Intermediate Similarity	NPC188968
0.8218	Intermediate Similarity	NPC167974
0.8218	Intermediate Similarity	NPC476195
0.8211	Intermediate Similarity	NPC470620
0.8211	Intermediate Similarity	NPC149224
0.8208	Intermediate Similarity	NPC177047
0.8208	Intermediate Similarity	NPC170974
0.8208	Intermediate Similarity	NPC191439
0.8208	Intermediate Similarity	NPC475563
0.8208	Intermediate Similarity	NPC103627
0.8208	Intermediate Similarity	NPC475134
0.82	Intermediate Similarity	NPC473244
0.8191	Intermediate Similarity	NPC157257
0.8191	Intermediate Similarity	NPC35933
0.8191	Intermediate Similarity	NPC266511
0.819	Intermediate Similarity	NPC50124
0.819	Intermediate Similarity	NPC38217
0.819	Intermediate Similarity	NPC258323
0.819	Intermediate Similarity	NPC472988
0.8182	Intermediate Similarity	NPC276110
0.8182	Intermediate Similarity	NPC257457
0.8182	Intermediate Similarity	NPC311554
0.8173	Intermediate Similarity	NPC119855
0.8173	Intermediate Similarity	NPC220217
0.8173	Intermediate Similarity	NPC471206
0.8173	Intermediate Similarity	NPC51719
0.8172	Intermediate Similarity	NPC207013
0.8165	Intermediate Similarity	NPC146652
0.8165	Intermediate Similarity	NPC207637
0.8165	Intermediate Similarity	NPC310341
0.8165	Intermediate Similarity	NPC199428
0.8165	Intermediate Similarity	NPC193382
0.8165	Intermediate Similarity	NPC470075
0.8165	Intermediate Similarity	NPC99620
0.8165	Intermediate Similarity	NPC5311
0.8163	Intermediate Similarity	NPC307776
0.8155	Intermediate Similarity	NPC97487
0.8155	Intermediate Similarity	NPC112009
0.8155	Intermediate Similarity	NPC475334
0.8155	Intermediate Similarity	NPC187302
0.8155	Intermediate Similarity	NPC475623
0.8155	Intermediate Similarity	NPC180204
0.8155	Intermediate Similarity	NPC196471
0.8155	Intermediate Similarity	NPC473694
0.8155	Intermediate Similarity	NPC189588
0.8155	Intermediate Similarity	NPC297617
0.8155	Intermediate Similarity	NPC160583
0.8155	Intermediate Similarity	NPC10232
0.8148	Intermediate Similarity	NPC250109
0.8144	Intermediate Similarity	NPC78973
0.8144	Intermediate Similarity	NPC471896
0.8137	Intermediate Similarity	NPC268829
0.8137	Intermediate Similarity	NPC222875
0.8137	Intermediate Similarity	NPC247701
0.8137	Intermediate Similarity	NPC470054
0.8137	Intermediate Similarity	NPC476132
0.8137	Intermediate Similarity	NPC25177
0.8137	Intermediate Similarity	NPC295110
0.8131	Intermediate Similarity	NPC285410
0.8131	Intermediate Similarity	NPC65167
0.8131	Intermediate Similarity	NPC263827
0.8131	Intermediate Similarity	NPC475668
0.8131	Intermediate Similarity	NPC475480
0.8131	Intermediate Similarity	NPC473921
0.8131	Intermediate Similarity	NPC250481
0.8125	Intermediate Similarity	NPC133588
0.8125	Intermediate Similarity	NPC474668
0.8119	Intermediate Similarity	NPC476895
0.8119	Intermediate Similarity	NPC247233
0.8113	Intermediate Similarity	NPC14630
0.8113	Intermediate Similarity	NPC473318
0.8113	Intermediate Similarity	NPC475065
0.8113	Intermediate Similarity	NPC250089
0.8113	Intermediate Similarity	NPC28844
0.8113	Intermediate Similarity	NPC157530
0.8113	Intermediate Similarity	NPC40728
0.8113	Intermediate Similarity	NPC472901
0.8113	Intermediate Similarity	NPC473328
0.8108	Intermediate Similarity	NPC470897
0.8108	Intermediate Similarity	NPC32177
0.8108	Intermediate Similarity	NPC5883
0.8108	Intermediate Similarity	NPC30483
0.8108	Intermediate Similarity	NPC44899
0.8108	Intermediate Similarity	NPC304260
0.8108	Intermediate Similarity	NPC292467
0.8108	Intermediate Similarity	NPC477071
0.8108	Intermediate Similarity	NPC469756
0.8108	Intermediate Similarity	NPC29639
0.8108	Intermediate Similarity	NPC329905

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 NPC230546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1443
0.2-0.3	3958
0.3-0.4	2383
0.4-0.5	700
0.5-0.6	228
0.6-0.7	194
0.7-0.8	90
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD7516	Approved
0.8036	Intermediate Similarity	NPD8377	Approved
0.8036	Intermediate Similarity	NPD8294	Approved
0.8018	Intermediate Similarity	NPD7328	Approved
0.8018	Intermediate Similarity	NPD7327	Approved
0.7965	Intermediate Similarity	NPD8380	Approved
0.7965	Intermediate Similarity	NPD8379	Approved
0.7965	Intermediate Similarity	NPD8296	Approved
0.7965	Intermediate Similarity	NPD8378	Approved
0.7965	Intermediate Similarity	NPD8335	Approved
0.7965	Intermediate Similarity	NPD8033	Approved
0.7941	Intermediate Similarity	NPD7638	Approved
0.7928	Intermediate Similarity	NPD7115	Discovery
0.789	Intermediate Similarity	NPD8297	Approved
0.7864	Intermediate Similarity	NPD7639	Approved
0.7864	Intermediate Similarity	NPD7640	Approved
0.7857	Intermediate Similarity	NPD6051	Approved
0.7849	Intermediate Similarity	NPD7525	Registered
0.7807	Intermediate Similarity	NPD7503	Approved
0.7767	Intermediate Similarity	NPD4225	Approved
0.7664	Intermediate Similarity	NPD6402	Approved
0.7664	Intermediate Similarity	NPD7128	Approved
0.7664	Intermediate Similarity	NPD6675	Approved
0.7664	Intermediate Similarity	NPD5739	Approved
0.7624	Intermediate Similarity	NPD6399	Phase 3
0.7615	Intermediate Similarity	NPD6372	Approved
0.7615	Intermediate Similarity	NPD6373	Approved
0.7615	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7507	Approved
0.7523	Intermediate Similarity	NPD6899	Approved
0.7523	Intermediate Similarity	NPD6881	Approved
0.7523	Intermediate Similarity	NPD7320	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7477	Intermediate Similarity	NPD8130	Phase 1
0.7475	Intermediate Similarity	NPD7524	Approved
0.7431	Intermediate Similarity	NPD5701	Approved
0.7431	Intermediate Similarity	NPD5697	Approved
0.7411	Intermediate Similarity	NPD6882	Approved
0.7387	Intermediate Similarity	NPD7290	Approved
0.7387	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6883	Approved
0.7387	Intermediate Similarity	NPD7102	Approved
0.7364	Intermediate Similarity	NPD6686	Approved
0.7355	Intermediate Similarity	NPD7319	Approved
0.7353	Intermediate Similarity	NPD8035	Phase 2
0.7353	Intermediate Similarity	NPD8034	Phase 2
0.7345	Intermediate Similarity	NPD8133	Approved
0.7333	Intermediate Similarity	NPD6083	Phase 2
0.7333	Intermediate Similarity	NPD6084	Phase 2
0.7321	Intermediate Similarity	NPD6617	Approved
0.7321	Intermediate Similarity	NPD6869	Approved
0.7321	Intermediate Similarity	NPD6847	Approved
0.7312	Intermediate Similarity	NPD6942	Approved
0.7312	Intermediate Similarity	NPD7339	Approved
0.7297	Intermediate Similarity	NPD6013	Approved
0.7297	Intermediate Similarity	NPD6014	Approved
0.7297	Intermediate Similarity	NPD6012	Approved
0.729	Intermediate Similarity	NPD5344	Discontinued
0.729	Intermediate Similarity	NPD4159	Approved
0.7265	Intermediate Similarity	NPD6319	Approved
0.7222	Intermediate Similarity	NPD7632	Discontinued
0.7212	Intermediate Similarity	NPD7748	Approved
0.7207	Intermediate Similarity	NPD6011	Approved
0.7193	Intermediate Similarity	NPD4632	Approved
0.7188	Intermediate Similarity	NPD7645	Phase 2
0.7172	Intermediate Similarity	NPD4786	Approved
0.7172	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4755	Approved
0.717	Intermediate Similarity	NPD7902	Approved
0.7168	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4202	Approved
0.71	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6695	Phase 3
0.7064	Intermediate Similarity	NPD5211	Phase 2
0.7054	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6933	Approved
0.7037	Intermediate Similarity	NPD5286	Approved
0.7037	Intermediate Similarity	NPD4696	Approved
0.7037	Intermediate Similarity	NPD5285	Approved
0.7037	Intermediate Similarity	NPD4700	Approved
0.703	Intermediate Similarity	NPD3618	Phase 1
0.7019	Intermediate Similarity	NPD6079	Approved
0.7019	Intermediate Similarity	NPD7637	Suspended
0.7019	Intermediate Similarity	NPD7515	Phase 2
0.6981	Remote Similarity	NPD5695	Phase 3
0.697	Remote Similarity	NPD3667	Approved
0.6964	Remote Similarity	NPD6412	Phase 2
0.6961	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7750	Discontinued
0.6944	Remote Similarity	NPD5696	Approved
0.6937	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD6274	Approved
0.6911	Remote Similarity	NPD8293	Discontinued
0.6909	Remote Similarity	NPD5225	Approved
0.6909	Remote Similarity	NPD4633	Approved
0.6909	Remote Similarity	NPD5224	Approved
0.6909	Remote Similarity	NPD5226	Approved
0.6893	Remote Similarity	NPD6672	Approved
0.6893	Remote Similarity	NPD5737	Approved
0.6891	Remote Similarity	NPD7100	Approved
0.6891	Remote Similarity	NPD7101	Approved
0.6887	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7900	Approved
0.6885	Remote Similarity	NPD7492	Approved
0.6881	Remote Similarity	NPD6648	Approved
0.6875	Remote Similarity	NPD4768	Approved
0.6875	Remote Similarity	NPD4767	Approved
0.6864	Remote Similarity	NPD6009	Approved
0.6863	Remote Similarity	NPD7146	Approved
0.6863	Remote Similarity	NPD7334	Approved
0.6863	Remote Similarity	NPD6409	Approved
0.6863	Remote Similarity	NPD5330	Approved
0.6863	Remote Similarity	NPD7521	Approved
0.6863	Remote Similarity	NPD6684	Approved
0.6857	Remote Similarity	NPD5693	Phase 1
0.6855	Remote Similarity	NPD7736	Approved
0.6847	Remote Similarity	NPD5174	Approved
0.6847	Remote Similarity	NPD5175	Approved
0.6842	Remote Similarity	NPD6926	Approved
0.6842	Remote Similarity	NPD6924	Approved
0.6833	Remote Similarity	NPD6059	Approved
0.6833	Remote Similarity	NPD6054	Approved
0.6829	Remote Similarity	NPD6616	Approved
0.6827	Remote Similarity	NPD4753	Phase 2
0.6822	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5223	Approved
0.681	Remote Similarity	NPD6053	Discontinued
0.6809	Remote Similarity	NPD4243	Approved
0.6807	Remote Similarity	NPD6335	Approved
0.6803	Remote Similarity	NPD7604	Phase 2
0.6783	Remote Similarity	NPD4634	Approved
0.6777	Remote Similarity	NPD6908	Approved
0.6777	Remote Similarity	NPD5983	Phase 2
0.6777	Remote Similarity	NPD6909	Approved
0.6774	Remote Similarity	NPD7078	Approved
0.6774	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6931	Approved
0.6768	Remote Similarity	NPD6930	Phase 2
0.6765	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7838	Discovery
0.6759	Remote Similarity	NPD5221	Approved
0.6759	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5222	Approved
0.6759	Remote Similarity	NPD4697	Phase 3
0.6754	Remote Similarity	NPD4730	Approved
0.6754	Remote Similarity	NPD4729	Approved
0.6731	Remote Similarity	NPD6903	Approved
0.6731	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6008	Approved
0.6723	Remote Similarity	NPD6317	Approved
0.6721	Remote Similarity	NPD6370	Approved
0.6699	Remote Similarity	NPD6098	Approved
0.6697	Remote Similarity	NPD5173	Approved
0.6696	Remote Similarity	NPD4754	Approved
0.6694	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD8513	Phase 3
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD8517	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6639	Remote Similarity	NPD8516	Approved
0.6639	Remote Similarity	NPD8515	Approved
0.6638	Remote Similarity	NPD5250	Approved
0.6638	Remote Similarity	NPD5248	Approved
0.6638	Remote Similarity	NPD5249	Phase 3
0.6638	Remote Similarity	NPD5247	Approved
0.6638	Remote Similarity	NPD5251	Approved
0.6634	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6116	Phase 1
0.6609	Remote Similarity	NPD5128	Approved
0.6604	Remote Similarity	NPD6698	Approved
0.6604	Remote Similarity	NPD46	Approved
0.66	Remote Similarity	NPD7509	Discontinued
0.66	Remote Similarity	NPD4748	Discontinued
0.66	Remote Similarity	NPD7514	Phase 3
0.6585	Remote Similarity	NPD5988	Approved
0.6583	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5284	Approved
0.6542	Remote Similarity	NPD7087	Discontinued
0.6542	Remote Similarity	NPD5281	Approved
0.6542	Remote Similarity	NPD6411	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