NPASS Compound

Structure

NPC292793 OpenBabel07101719512D 34 37 0 0 1 0 0 0 0 0999 V2000 2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9792 -6.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2361 -5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -3.0032 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 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 -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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 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 -4.3301 1.5000 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 2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 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 -1.7321 0.0000 0.0000 C 0 0 1 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 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 -5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 26 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 31 2 0 0 0 0 19 1 1 6 0 0 0 19 20 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 30 1 6 0 0 0 22 27 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 27 1 0 0 0 0 24 33 1 6 0 0 0 25 29 1 1 0 0 0 25 30 1 0 0 0 0 26 34 1 0 0 0 0 28 29 1 6 0 0 0 29 7 1 1 0 0 0 30 18 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	4.436
LogD:	4.141
LogS:	-4.087
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	5.332
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	2.1400848709163256e-05
Pgp-inhibitor:	0.88
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.75

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	78.52289581298828%
Volume Distribution (VD):	0.867
Pgp-substrate:	12.483870506286621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.467
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.921
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	6.825
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.115
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.896
Carcinogencity:	0.255
Eye Corrosion:	0.006
Eye Irritation:	0.026
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC292793

Natural Product ID:	NPC292793
*Common Name:**	3Beta,7Beta,25-Trihydroxycucurbita-5,23(E)-Dien-19-Al
IUPAC Name:	(3S,7S,8S,9R,10R,13R,14S,17R)-3,7-dihydroxy-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-4,4,13,14-tetramethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-9-carbaldehyde
Synonyms:
Standard InCHIKey:	DIAXRIQADLDGOJ-TZFKRHLPSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-19(9-8-13-26(2,3)34)20-12-14-29(7)25-23(32)17-22-21(10-11-24(33)27(22,4)5)30(25,18-31)16-15-28(20,29)6/h8,13,17-21,23-25,32-34H,9-12,14-16H2,1-7H3/b13-8+/t19-,20-,21-,23+,24+,25+,28-,29+,30-/m1/s1
SMILES:	O=C[C@]12CC[C@]3([C@@]([C@@H]2[C@H](C=C2[C@H]1CC[C@@H](C2(C)C)O)O)(C)CC[C@@H]3[C@@H](C/C=C/C(O)(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468859
PubChem CID:	44577792
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17685651]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[18637688]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24836069]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621938]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Vines	n.a.	n.a.	PMID[32357011]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	1
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1086	Cell Line	SK-HEP1	Homo sapiens	IC50	=	98300.0	nM	PMID[558873]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	-15.0	%	PMID[558874]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	-5.0	%	PMID[558874]

☑ 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 NPC292793 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	166
0.1-0.2	1042
0.2-0.3	4223
0.3-0.4	12564
0.4-0.5	10149
0.5-0.6	6651
0.6-0.7	5307
0.7-0.8	2238
0.8-0.85	285
0.85-0.9	67
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC126815
0.9451	High Similarity	NPC291634
0.913	High Similarity	NPC78473
0.9	High Similarity	NPC48010
0.8913	High Similarity	NPC8993
0.8901	High Similarity	NPC475806
0.8889	High Similarity	NPC32830
0.8889	High Similarity	NPC2983
0.8889	High Similarity	NPC474245
0.8864	High Similarity	NPC471224
0.8817	High Similarity	NPC271195
0.8791	High Similarity	NPC320026
0.8764	High Similarity	NPC94755
0.8763	High Similarity	NPC249187
0.8763	High Similarity	NPC247957
0.875	High Similarity	NPC205845
0.875	High Similarity	NPC59453
0.875	High Similarity	NPC221758
0.8736	High Similarity	NPC49964
0.8723	High Similarity	NPC249954
0.8696	High Similarity	NPC473998
0.8681	High Similarity	NPC473999
0.8681	High Similarity	NPC309603
0.8681	High Similarity	NPC31985
0.8681	High Similarity	NPC1015
0.8667	High Similarity	NPC475740
0.8667	High Similarity	NPC58063
0.8652	High Similarity	NPC474083
0.8646	High Similarity	NPC154072
0.8632	High Similarity	NPC107243
0.8621	High Similarity	NPC264245
0.8617	High Similarity	NPC259286
0.8602	High Similarity	NPC474736
0.8587	High Similarity	NPC469400
0.8586	High Similarity	NPC166607
0.8586	High Similarity	NPC257353
0.8556	High Similarity	NPC51014
0.8556	High Similarity	NPC145879
0.8556	High Similarity	NPC474732
0.8556	High Similarity	NPC31564
0.8556	High Similarity	NPC474778
0.8556	High Similarity	NPC469994
0.8556	High Similarity	NPC474733
0.8556	High Similarity	NPC155011
0.8556	High Similarity	NPC261266
0.8542	High Similarity	NPC103051
0.8526	High Similarity	NPC235053
0.8523	High Similarity	NPC151519
0.8523	High Similarity	NPC101462
0.8511	High Similarity	NPC474690
0.8511	High Similarity	NPC299100
0.8511	High Similarity	NPC469406
0.8506	High Similarity	NPC209944
0.8506	High Similarity	NPC234193
0.8506	High Similarity	NPC164840
0.8506	High Similarity	NPC241290
0.85	High Similarity	NPC185
0.8485	Intermediate Similarity	NPC72255
0.8485	Intermediate Similarity	NPC160843
0.8478	Intermediate Similarity	NPC475921
0.8478	Intermediate Similarity	NPC474704
0.8478	Intermediate Similarity	NPC76879
0.8469	Intermediate Similarity	NPC477915
0.8469	Intermediate Similarity	NPC87351
0.8462	Intermediate Similarity	NPC474684
0.8462	Intermediate Similarity	NPC142361
0.8462	Intermediate Similarity	NPC90652
0.8462	Intermediate Similarity	NPC128644
0.8462	Intermediate Similarity	NPC317590
0.8462	Intermediate Similarity	NPC149224
0.8444	Intermediate Similarity	NPC274448
0.8444	Intermediate Similarity	NPC269638
0.8444	Intermediate Similarity	NPC474218
0.8438	Intermediate Similarity	NPC474938
0.8438	Intermediate Similarity	NPC474785
0.8438	Intermediate Similarity	NPC57416
0.8427	Intermediate Similarity	NPC474634
0.8421	Intermediate Similarity	NPC53565
0.8421	Intermediate Similarity	NPC180950
0.8409	Intermediate Similarity	NPC47761
0.8404	Intermediate Similarity	NPC472930
0.8404	Intermediate Similarity	NPC470376
0.8404	Intermediate Similarity	NPC472942
0.8404	Intermediate Similarity	NPC470375
0.8404	Intermediate Similarity	NPC69454
0.84	Intermediate Similarity	NPC149047
0.8391	Intermediate Similarity	NPC84694
0.8391	Intermediate Similarity	NPC143182
0.8391	Intermediate Similarity	NPC109546
0.8391	Intermediate Similarity	NPC28862
0.8391	Intermediate Similarity	NPC47982
0.8391	Intermediate Similarity	NPC81306
0.8387	Intermediate Similarity	NPC472476
0.8387	Intermediate Similarity	NPC69622
0.8387	Intermediate Similarity	NPC191684
0.8384	Intermediate Similarity	NPC311612
0.8384	Intermediate Similarity	NPC26478
0.837	Intermediate Similarity	NPC193360
0.837	Intermediate Similarity	NPC53911
0.837	Intermediate Similarity	NPC242864
0.837	Intermediate Similarity	NPC470417
0.837	Intermediate Similarity	NPC328313
0.837	Intermediate Similarity	NPC472483
0.837	Intermediate Similarity	NPC471722
0.8367	Intermediate Similarity	NPC476897
0.8352	Intermediate Similarity	NPC475022
0.8352	Intermediate Similarity	NPC470955
0.8352	Intermediate Similarity	NPC6391
0.8352	Intermediate Similarity	NPC222613
0.8352	Intermediate Similarity	NPC118648
0.8352	Intermediate Similarity	NPC82979
0.8351	Intermediate Similarity	NPC48647
0.8351	Intermediate Similarity	NPC186810
0.8333	Intermediate Similarity	NPC214043
0.8333	Intermediate Similarity	NPC214644
0.8333	Intermediate Similarity	NPC165064
0.8333	Intermediate Similarity	NPC192428
0.8333	Intermediate Similarity	NPC117133
0.8333	Intermediate Similarity	NPC471463
0.8333	Intermediate Similarity	NPC185568
0.8333	Intermediate Similarity	NPC85774
0.8333	Intermediate Similarity	NPC82902
0.8317	Intermediate Similarity	NPC475060
0.8317	Intermediate Similarity	NPC220229
0.8316	Intermediate Similarity	NPC196485
0.8316	Intermediate Similarity	NPC245972
0.8315	Intermediate Similarity	NPC87489
0.8315	Intermediate Similarity	NPC296701
0.8315	Intermediate Similarity	NPC50964
0.8315	Intermediate Similarity	NPC218616
0.83	Intermediate Similarity	NPC209502
0.83	Intermediate Similarity	NPC204833
0.8298	Intermediate Similarity	NPC63748
0.8298	Intermediate Similarity	NPC212301
0.8298	Intermediate Similarity	NPC189520
0.8298	Intermediate Similarity	NPC233116
0.8298	Intermediate Similarity	NPC86266
0.8298	Intermediate Similarity	NPC110657
0.8298	Intermediate Similarity	NPC272746
0.8283	Intermediate Similarity	NPC136289
0.8283	Intermediate Similarity	NPC185530
0.8283	Intermediate Similarity	NPC473424
0.828	Intermediate Similarity	NPC268406
0.828	Intermediate Similarity	NPC128496
0.828	Intermediate Similarity	NPC472970
0.828	Intermediate Similarity	NPC119416
0.828	Intermediate Similarity	NPC469319
0.828	Intermediate Similarity	NPC472971
0.828	Intermediate Similarity	NPC186688
0.828	Intermediate Similarity	NPC472477
0.828	Intermediate Similarity	NPC229871
0.828	Intermediate Similarity	NPC26959
0.828	Intermediate Similarity	NPC472475
0.828	Intermediate Similarity	NPC477943
0.828	Intermediate Similarity	NPC472983
0.828	Intermediate Similarity	NPC146554
0.8276	Intermediate Similarity	NPC474216
0.8261	Intermediate Similarity	NPC472482
0.8261	Intermediate Similarity	NPC472484
0.8261	Intermediate Similarity	NPC159046
0.8261	Intermediate Similarity	NPC233836
0.8261	Intermediate Similarity	NPC187376
0.8261	Intermediate Similarity	NPC472481
0.8247	Intermediate Similarity	NPC320306
0.8247	Intermediate Similarity	NPC475894
0.8247	Intermediate Similarity	NPC108078
0.8242	Intermediate Similarity	NPC470574
0.8242	Intermediate Similarity	NPC157257
0.8242	Intermediate Similarity	NPC266511
0.8242	Intermediate Similarity	NPC469948
0.8242	Intermediate Similarity	NPC318390
0.8235	Intermediate Similarity	NPC472218
0.8235	Intermediate Similarity	NPC472217
0.8235	Intermediate Similarity	NPC472219
0.8235	Intermediate Similarity	NPC177064
0.8235	Intermediate Similarity	NPC217201
0.8229	Intermediate Similarity	NPC290481
0.8229	Intermediate Similarity	NPC318282
0.8229	Intermediate Similarity	NPC472485
0.8229	Intermediate Similarity	NPC174948
0.8229	Intermediate Similarity	NPC469995
0.8229	Intermediate Similarity	NPC472932
0.8229	Intermediate Similarity	NPC469599
0.8229	Intermediate Similarity	NPC173875
0.8222	Intermediate Similarity	NPC278648
0.8222	Intermediate Similarity	NPC475789
0.8222	Intermediate Similarity	NPC476082
0.8218	Intermediate Similarity	NPC48733
0.8218	Intermediate Similarity	NPC150531
0.8218	Intermediate Similarity	NPC202167
0.8218	Intermediate Similarity	NPC319077
0.8218	Intermediate Similarity	NPC296945
0.8218	Intermediate Similarity	NPC49958
0.8218	Intermediate Similarity	NPC302607
0.8218	Intermediate Similarity	NPC97202
0.8218	Intermediate Similarity	NPC50692
0.8218	Intermediate Similarity	NPC214264
0.8218	Intermediate Similarity	NPC476027
0.8218	Intermediate Similarity	NPC152695
0.8218	Intermediate Similarity	NPC85829

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 NPC292793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1307
0.2-0.3	3825
0.3-0.4	2625
0.4-0.5	747
0.5-0.6	180
0.6-0.7	150
0.7-0.8	146
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD4786	Approved
0.8523	High Similarity	NPD3667	Approved
0.8352	Intermediate Similarity	NPD3618	Phase 1
0.8333	Intermediate Similarity	NPD4697	Phase 3
0.8298	Intermediate Similarity	NPD6079	Approved
0.828	Intermediate Similarity	NPD5328	Approved
0.8211	Intermediate Similarity	NPD6399	Phase 3
0.81	Intermediate Similarity	NPD5211	Phase 2
0.8021	Intermediate Similarity	NPD4202	Approved
0.7959	Intermediate Similarity	NPD5221	Approved
0.7959	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5222	Approved
0.7941	Intermediate Similarity	NPD5141	Approved
0.7935	Intermediate Similarity	NPD3666	Approved
0.7935	Intermediate Similarity	NPD3133	Approved
0.7935	Intermediate Similarity	NPD3665	Phase 1
0.7935	Intermediate Similarity	NPD3668	Phase 3
0.7931	Intermediate Similarity	NPD6942	Approved
0.7931	Intermediate Similarity	NPD7339	Approved
0.79	Intermediate Similarity	NPD5286	Approved
0.79	Intermediate Similarity	NPD4696	Approved
0.79	Intermediate Similarity	NPD5285	Approved
0.7895	Intermediate Similarity	NPD4753	Phase 2
0.7889	Intermediate Similarity	NPD7525	Registered
0.7879	Intermediate Similarity	NPD5173	Approved
0.7879	Intermediate Similarity	NPD4755	Approved
0.7857	Intermediate Similarity	NPD5210	Approved
0.7857	Intermediate Similarity	NPD4629	Approved
0.7822	Intermediate Similarity	NPD5223	Approved
0.7798	Intermediate Similarity	NPD7115	Discovery
0.7745	Intermediate Similarity	NPD5226	Approved
0.7745	Intermediate Similarity	NPD5225	Approved
0.7745	Intermediate Similarity	NPD4633	Approved
0.7745	Intermediate Similarity	NPD5224	Approved
0.7723	Intermediate Similarity	NPD4700	Approved
0.7717	Intermediate Similarity	NPD4221	Approved
0.7717	Intermediate Similarity	NPD4223	Phase 3
0.7684	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5174	Approved
0.767	Intermediate Similarity	NPD5175	Approved
0.766	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5329	Approved
0.764	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4623	Approved
0.7579	Intermediate Similarity	NPD4519	Discontinued
0.7579	Intermediate Similarity	NPD5279	Phase 3
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4197	Approved
0.7551	Intermediate Similarity	NPD7515	Phase 2
0.7549	Intermediate Similarity	NPD7639	Approved
0.7549	Intermediate Similarity	NPD7640	Approved
0.7547	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD6881	Approved
0.7525	Intermediate Similarity	NPD6084	Phase 2
0.7525	Intermediate Similarity	NPD6083	Phase 2
0.7524	Intermediate Similarity	NPD7128	Approved
0.7524	Intermediate Similarity	NPD6402	Approved
0.7524	Intermediate Similarity	NPD5739	Approved
0.7524	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD6372	Approved
0.7473	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5697	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.7447	Intermediate Similarity	NPD4788	Approved
0.7416	Intermediate Similarity	NPD6926	Approved
0.7416	Intermediate Similarity	NPD4785	Approved
0.7416	Intermediate Similarity	NPD6924	Approved
0.7416	Intermediate Similarity	NPD4784	Approved
0.7407	Intermediate Similarity	NPD7290	Approved
0.7407	Intermediate Similarity	NPD6883	Approved
0.7407	Intermediate Similarity	NPD7102	Approved
0.7396	Intermediate Similarity	NPD4693	Phase 3
0.7396	Intermediate Similarity	NPD4138	Approved
0.7396	Intermediate Similarity	NPD5205	Approved
0.7396	Intermediate Similarity	NPD4688	Approved
0.7396	Intermediate Similarity	NPD5690	Phase 2
0.7396	Intermediate Similarity	NPD4690	Approved
0.7396	Intermediate Similarity	NPD4689	Approved
0.7383	Intermediate Similarity	NPD4729	Approved
0.7383	Intermediate Similarity	NPD6011	Approved
0.7383	Intermediate Similarity	NPD7320	Approved
0.7383	Intermediate Similarity	NPD4730	Approved
0.7374	Intermediate Similarity	NPD5281	Approved
0.7374	Intermediate Similarity	NPD5284	Approved
0.7374	Intermediate Similarity	NPD8035	Phase 2
0.7374	Intermediate Similarity	NPD8034	Phase 2
0.7358	Intermediate Similarity	NPD4768	Approved
0.7358	Intermediate Similarity	NPD4767	Approved
0.7339	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD8130	Phase 1
0.7339	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.7312	Intermediate Similarity	NPD6930	Phase 2
0.7312	Intermediate Similarity	NPD7514	Phase 3
0.7312	Intermediate Similarity	NPD6931	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7283	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5696	Approved
0.7273	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7263	Intermediate Similarity	NPD5362	Discontinued
0.7263	Intermediate Similarity	NPD6695	Phase 3
0.7253	Intermediate Similarity	NPD6933	Approved
0.7248	Intermediate Similarity	NPD5247	Approved
0.7248	Intermediate Similarity	NPD5251	Approved
0.7248	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4634	Approved
0.7248	Intermediate Similarity	NPD5135	Approved
0.7248	Intermediate Similarity	NPD5249	Phase 3
0.7248	Intermediate Similarity	NPD5250	Approved
0.7248	Intermediate Similarity	NPD5169	Approved
0.7248	Intermediate Similarity	NPD5248	Approved
0.7245	Intermediate Similarity	NPD6672	Approved
0.7245	Intermediate Similarity	NPD5737	Approved
0.7228	Intermediate Similarity	NPD7748	Approved
0.7222	Intermediate Similarity	NPD5128	Approved
0.7222	Intermediate Similarity	NPD5168	Approved
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7216	Intermediate Similarity	NPD4694	Approved
0.7216	Intermediate Similarity	NPD5280	Approved
0.7204	Intermediate Similarity	NPD6929	Approved
0.7204	Intermediate Similarity	NPD4195	Approved
0.72	Intermediate Similarity	NPD7637	Suspended
0.7191	Intermediate Similarity	NPD7152	Approved
0.7191	Intermediate Similarity	NPD4243	Approved
0.7191	Intermediate Similarity	NPD7150	Approved
0.7191	Intermediate Similarity	NPD7151	Approved
0.7188	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7902	Approved
0.7182	Intermediate Similarity	NPD5217	Approved
0.7182	Intermediate Similarity	NPD5127	Approved
0.7182	Intermediate Similarity	NPD5216	Approved
0.7182	Intermediate Similarity	NPD5215	Approved
0.7182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4269	Approved
0.7158	Intermediate Similarity	NPD4270	Approved
0.7157	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7128	Intermediate Similarity	NPD4695	Discontinued
0.7128	Intermediate Similarity	NPD7332	Phase 2
0.7097	Intermediate Similarity	NPD7145	Approved
0.7097	Intermediate Similarity	NPD3617	Approved
0.7079	Intermediate Similarity	NPD7143	Approved
0.7079	Intermediate Similarity	NPD7144	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7071	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6117	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.7053	Intermediate Similarity	NPD6902	Approved
0.7053	Intermediate Similarity	NPD4692	Approved
0.7053	Intermediate Similarity	NPD4139	Approved
0.7041	Intermediate Similarity	NPD6098	Approved
0.7037	Intermediate Similarity	NPD6008	Approved
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6080	Approved
0.6991	Remote Similarity	NPD5167	Approved
0.6989	Remote Similarity	NPD6116	Phase 1
0.6989	Remote Similarity	NPD6925	Approved
0.6989	Remote Similarity	NPD6932	Approved
0.6989	Remote Similarity	NPD5776	Phase 2
0.697	Remote Similarity	NPD7750	Discontinued
0.697	Remote Similarity	NPD7524	Approved
0.6966	Remote Similarity	NPD6923	Approved
0.6966	Remote Similarity	NPD6922	Approved
0.6957	Remote Similarity	NPD6335	Approved
0.6957	Remote Similarity	NPD8264	Approved
0.6952	Remote Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD4820	Approved
0.6947	Remote Similarity	NPD4819	Approved
0.6947	Remote Similarity	NPD4748	Discontinued
0.6947	Remote Similarity	NPD4821	Approved
0.6947	Remote Similarity	NPD4822	Approved
0.6947	Remote Similarity	NPD4252	Approved
0.6939	Remote Similarity	NPD6893	Approved
0.6939	Remote Similarity	NPD5363	Approved
0.6931	Remote Similarity	NPD5785	Approved
0.693	Remote Similarity	NPD6868	Approved
0.6916	Remote Similarity	NPD7632	Discontinued
0.6916	Remote Similarity	NPD5091	Approved
0.6915	Remote Similarity	NPD6115	Approved
0.6915	Remote Similarity	NPD6114	Approved
0.6915	Remote Similarity	NPD6697	Approved
0.6915	Remote Similarity	NPD6118	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