NPASS Compound

Structure

CID182815 OpenBabel06191715562D 29 32 0 0 1 0 0 0 0 0999 V2000 -3.9961 6.3807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5373 5.6940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2031 4.6010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8066 3.7112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5343 2.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7443 3.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3479 3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6888 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2220 1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2217 0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5685 5.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1720 4.7026 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3790 2.9229 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9752 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6882 -0.9747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3787 1.9488 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5338 0.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8447 0.4873 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 -2.5340 1.4614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5544 -1.4744 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 7 8 2 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 23 2 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 20 24 1 0 0 0 0 21 27 1 0 0 0 0 22 29 2 0 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 28 1 6 0 0 0 25 28 1 6 0 0 0 26 27 1 6 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.34
Volume:	459.499
LogP:	6.864
LogD:	6.137
LogS:	-6.625
# Rotatable Bonds:	4
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.447
Synthetic Accessibility Score:	4.638
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.68
MDCK Permeability:	2.3712695110589266e-05
Pgp-inhibitor:	0.76
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	89.0543441772461%
Volume Distribution (VD):	1.242
Pgp-substrate:	1.4387606382369995%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.531
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.679
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.834

ADMET: Excretion

Clearance (CL):	2.393
Half-life (T1/2):	0.118

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.607
Skin Sensitization:	0.047
Carcinogencity:	0.004
Eye Corrosion:	0.021
Eye Irritation:	0.195
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC182815

Natural Product ID:	NPC182815
*Common Name:**	Ergosta-7,22-Dien-3-One
IUPAC Name:	(9R,10S,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,4,5,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	AHWOEMBXZXGDBQ-MERCMEHUSA-N
Standard InCHI:	InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-8,10,18-21,24-26H,9,11-17H2,1-6H3/b8-7+/t19-,20+,21?,24+,25-,26-,27-,28+/m0/s1
SMILES:	CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CCC4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516711
PubChem CID:	6436804
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	71.12	%	PMID[533350]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	94.39	%	PMID[533350]

☑ 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 NPC182815 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	180
0.1-0.2	2001
0.2-0.3	13554
0.3-0.4	12276
0.4-0.5	7231
0.5-0.6	4941
0.6-0.7	2002
0.7-0.8	431
0.8-0.85	39
0.85-0.9	16
0.9-0.95	17
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC20610
0.9697	High Similarity	NPC115023
0.9697	High Similarity	NPC470078
0.9552	High Similarity	NPC251705
0.9545	High Similarity	NPC282593
0.9545	High Similarity	NPC159577
0.9545	High Similarity	NPC35734
0.9531	High Similarity	NPC323005
0.9403	High Similarity	NPC234707
0.9275	High Similarity	NPC293803
0.9265	High Similarity	NPC470044
0.9265	High Similarity	NPC474228
0.9265	High Similarity	NPC470045
0.9265	High Similarity	NPC303613
0.9254	High Similarity	NPC307176
0.9254	High Similarity	NPC477856
0.9254	High Similarity	NPC214770
0.9254	High Similarity	NPC40574
0.9219	High Similarity	NPC469662
0.9143	High Similarity	NPC69408
0.913	High Similarity	NPC309852
0.9118	High Similarity	NPC54123
0.9118	High Similarity	NPC305501
0.9104	High Similarity	NPC139397
0.9062	High Similarity	NPC197238
0.9062	High Similarity	NPC202118
0.8971	High Similarity	NPC260040
0.8971	High Similarity	NPC265782
0.8971	High Similarity	NPC2634
0.8971	High Similarity	NPC251929
0.8889	High Similarity	NPC82635
0.8889	High Similarity	NPC470052
0.8857	High Similarity	NPC255021
0.8806	High Similarity	NPC176107
0.875	High Similarity	NPC91665
0.8732	High Similarity	NPC473171
0.8732	High Similarity	NPC255650
0.8676	High Similarity	NPC39157
0.8676	High Similarity	NPC82477
0.8676	High Similarity	NPC142754
0.8676	High Similarity	NPC296697
0.8657	High Similarity	NPC189917
0.8657	High Similarity	NPC96812
0.8657	High Similarity	NPC92327
0.8657	High Similarity	NPC39462
0.8657	High Similarity	NPC107704
0.8657	High Similarity	NPC168824
0.8657	High Similarity	NPC43300
0.8649	High Similarity	NPC474509
0.8592	High Similarity	NPC474797
0.8592	High Similarity	NPC329866
0.8592	High Similarity	NPC474796
0.8551	High Similarity	NPC286814
0.8529	High Similarity	NPC20181
0.8529	High Similarity	NPC220210
0.8493	Intermediate Similarity	NPC470557
0.8406	Intermediate Similarity	NPC260474
0.8406	Intermediate Similarity	NPC188292
0.8333	Intermediate Similarity	NPC213152
0.8333	Intermediate Similarity	NPC60565
0.831	Intermediate Similarity	NPC190035
0.831	Intermediate Similarity	NPC225467
0.831	Intermediate Similarity	NPC223187
0.831	Intermediate Similarity	NPC5701
0.831	Intermediate Similarity	NPC181204
0.8289	Intermediate Similarity	NPC147066
0.8286	Intermediate Similarity	NPC256846
0.8286	Intermediate Similarity	NPC477857
0.8281	Intermediate Similarity	NPC267626
0.8281	Intermediate Similarity	NPC230823
0.8281	Intermediate Similarity	NPC55004
0.8281	Intermediate Similarity	NPC49575
0.8267	Intermediate Similarity	NPC215843
0.8267	Intermediate Similarity	NPC90965
0.8267	Intermediate Similarity	NPC170793
0.8209	Intermediate Similarity	NPC165695
0.8194	Intermediate Similarity	NPC474488
0.8182	Intermediate Similarity	NPC127582
0.8182	Intermediate Similarity	NPC320514
0.8182	Intermediate Similarity	NPC472239
0.8143	Intermediate Similarity	NPC87141
0.8143	Intermediate Similarity	NPC310992
0.8133	Intermediate Similarity	NPC469996
0.8116	Intermediate Similarity	NPC176171
0.8108	Intermediate Similarity	NPC469793
0.8108	Intermediate Similarity	NPC469796
0.8108	Intermediate Similarity	NPC474463
0.8101	Intermediate Similarity	NPC29447
0.8088	Intermediate Similarity	NPC475124
0.8088	Intermediate Similarity	NPC212210
0.8088	Intermediate Similarity	NPC285371
0.8077	Intermediate Similarity	NPC21667
0.8077	Intermediate Similarity	NPC470046
0.8077	Intermediate Similarity	NPC470047
0.8052	Intermediate Similarity	NPC201912
0.8052	Intermediate Similarity	NPC4166
0.8052	Intermediate Similarity	NPC38350
0.803	Intermediate Similarity	NPC276764
0.803	Intermediate Similarity	NPC472304
0.8026	Intermediate Similarity	NPC477371
0.7975	Intermediate Similarity	NPC221758
0.7975	Intermediate Similarity	NPC214043
0.7975	Intermediate Similarity	NPC59453
0.7975	Intermediate Similarity	NPC85774
0.7975	Intermediate Similarity	NPC82902
0.7971	Intermediate Similarity	NPC251118
0.7969	Intermediate Similarity	NPC200258
0.7949	Intermediate Similarity	NPC142253
0.7949	Intermediate Similarity	NPC260956
0.7949	Intermediate Similarity	NPC3511
0.7949	Intermediate Similarity	NPC472867
0.7949	Intermediate Similarity	NPC100297
0.7949	Intermediate Similarity	NPC193347
0.7949	Intermediate Similarity	NPC311092
0.7941	Intermediate Similarity	NPC472306
0.7922	Intermediate Similarity	NPC472478
0.791	Intermediate Similarity	NPC25853
0.7901	Intermediate Similarity	NPC93778
0.7901	Intermediate Similarity	NPC58063
0.7879	Intermediate Similarity	NPC30215
0.7879	Intermediate Similarity	NPC56905
0.7879	Intermediate Similarity	NPC266295
0.7879	Intermediate Similarity	NPC94991
0.7879	Intermediate Similarity	NPC27610
0.7875	Intermediate Similarity	NPC469948
0.7875	Intermediate Similarity	NPC474218
0.7875	Intermediate Similarity	NPC470223
0.7875	Intermediate Similarity	NPC471224
0.7848	Intermediate Similarity	NPC41539
0.7848	Intermediate Similarity	NPC83569
0.7848	Intermediate Similarity	NPC69279
0.7838	Intermediate Similarity	NPC159497
0.7821	Intermediate Similarity	NPC477372
0.7792	Intermediate Similarity	NPC190211
0.7778	Intermediate Similarity	NPC474778
0.7778	Intermediate Similarity	NPC474732
0.7778	Intermediate Similarity	NPC474733
0.7778	Intermediate Similarity	NPC469994
0.7778	Intermediate Similarity	NPC118648
0.7778	Intermediate Similarity	NPC51014
0.7778	Intermediate Similarity	NPC222613
0.7778	Intermediate Similarity	NPC475022
0.7778	Intermediate Similarity	NPC145879
0.7778	Intermediate Similarity	NPC31564
0.7778	Intermediate Similarity	NPC264127
0.7778	Intermediate Similarity	NPC470051
0.7778	Intermediate Similarity	NPC470050
0.7761	Intermediate Similarity	NPC259261
0.775	Intermediate Similarity	NPC181743
0.775	Intermediate Similarity	NPC473246
0.775	Intermediate Similarity	NPC144258
0.775	Intermediate Similarity	NPC16287
0.775	Intermediate Similarity	NPC87552
0.775	Intermediate Similarity	NPC237712
0.775	Intermediate Similarity	NPC178025
0.7746	Intermediate Similarity	NPC193770
0.7746	Intermediate Similarity	NPC475523
0.7727	Intermediate Similarity	NPC115385
0.7722	Intermediate Similarity	NPC133391
0.7722	Intermediate Similarity	NPC151519
0.7722	Intermediate Similarity	NPC469804
0.7722	Intermediate Similarity	NPC327969
0.7722	Intermediate Similarity	NPC240302
0.7722	Intermediate Similarity	NPC321289
0.7722	Intermediate Similarity	NPC469805
0.7722	Intermediate Similarity	NPC328351
0.7714	Intermediate Similarity	NPC268039
0.7711	Intermediate Similarity	NPC262043
0.7711	Intermediate Similarity	NPC2983
0.7692	Intermediate Similarity	NPC184819
0.7683	Intermediate Similarity	NPC476293
0.7683	Intermediate Similarity	NPC90652
0.7683	Intermediate Similarity	NPC475740
0.7683	Intermediate Similarity	NPC317590
0.7683	Intermediate Similarity	NPC96496
0.7683	Intermediate Similarity	NPC136948
0.7681	Intermediate Similarity	NPC288253
0.7671	Intermediate Similarity	NPC475728
0.7662	Intermediate Similarity	NPC105197
0.7662	Intermediate Similarity	NPC228911
0.7662	Intermediate Similarity	NPC115515
0.7654	Intermediate Similarity	NPC472931
0.7654	Intermediate Similarity	NPC474083
0.7654	Intermediate Similarity	NPC472940
0.7654	Intermediate Similarity	NPC11711
0.7654	Intermediate Similarity	NPC137493
0.7654	Intermediate Similarity	NPC8571
0.7654	Intermediate Similarity	NPC60350
0.7654	Intermediate Similarity	NPC470048
0.7647	Intermediate Similarity	NPC270042
0.7639	Intermediate Similarity	NPC155198
0.7632	Intermediate Similarity	NPC1254
0.7625	Intermediate Similarity	NPC477373
0.7625	Intermediate Similarity	NPC168188
0.7625	Intermediate Similarity	NPC477852
0.7625	Intermediate Similarity	NPC167103
0.7625	Intermediate Similarity	NPC3856
0.7625	Intermediate Similarity	NPC474976
0.7625	Intermediate Similarity	NPC474790
0.7625	Intermediate Similarity	NPC470015

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 NPC182815 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	2038
0.2-0.3	4667
0.3-0.4	1584
0.4-0.5	333
0.5-0.6	129
0.6-0.7	147
0.7-0.8	64
0.8-0.85	4
0.85-0.9	2
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9254	High Similarity	NPD4747	Approved
0.9242	High Similarity	NPD3621	Clinical (unspecified phase)
0.9104	High Similarity	NPD4137	Phase 3
0.8971	High Similarity	NPD4691	Approved
0.8857	High Similarity	NPD4687	Approved
0.8857	High Similarity	NPD4058	Approved
0.8857	High Similarity	NPD5733	Approved
0.8571	High Similarity	NPD5276	Approved
0.7975	Intermediate Similarity	NPD4786	Approved
0.7949	Intermediate Similarity	NPD4221	Approved
0.7949	Intermediate Similarity	NPD4223	Phase 3
0.7875	Intermediate Similarity	NPD5329	Approved
0.7778	Intermediate Similarity	NPD6098	Approved
0.775	Intermediate Similarity	NPD4197	Approved
0.7722	Intermediate Similarity	NPD3667	Approved
0.7625	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6672	Approved
0.759	Intermediate Similarity	NPD5737	Approved
0.7561	Intermediate Similarity	NPD4689	Approved
0.7561	Intermediate Similarity	NPD7146	Approved
0.7561	Intermediate Similarity	NPD4690	Approved
0.7561	Intermediate Similarity	NPD4693	Phase 3
0.7561	Intermediate Similarity	NPD7521	Approved
0.7561	Intermediate Similarity	NPD7334	Approved
0.7561	Intermediate Similarity	NPD5330	Approved
0.7561	Intermediate Similarity	NPD5205	Approved
0.7561	Intermediate Similarity	NPD4688	Approved
0.7561	Intermediate Similarity	NPD4138	Approved
0.7561	Intermediate Similarity	NPD6684	Approved
0.7561	Intermediate Similarity	NPD5690	Phase 2
0.7561	Intermediate Similarity	NPD6409	Approved
0.7531	Intermediate Similarity	NPD3666	Approved
0.7531	Intermediate Similarity	NPD3133	Approved
0.7531	Intermediate Similarity	NPD3668	Phase 3
0.7531	Intermediate Similarity	NPD3665	Phase 1
0.7529	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7436	Intermediate Similarity	NPD3617	Approved
0.7381	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6903	Approved
0.7381	Intermediate Similarity	NPD5208	Approved
0.7368	Intermediate Similarity	NPD4785	Approved
0.7368	Intermediate Similarity	NPD4784	Approved
0.7353	Intermediate Similarity	NPD287	Approved
0.7349	Intermediate Similarity	NPD3618	Phase 1
0.7349	Intermediate Similarity	NPD4694	Approved
0.7349	Intermediate Similarity	NPD5280	Approved
0.7342	Intermediate Similarity	NPD4195	Approved
0.7333	Intermediate Similarity	NPD4243	Approved
0.7294	Intermediate Similarity	NPD4753	Phase 2
0.7241	Intermediate Similarity	NPD6399	Phase 3
0.7209	Intermediate Similarity	NPD5207	Approved
0.716	Intermediate Similarity	NPD4692	Approved
0.716	Intermediate Similarity	NPD8028	Phase 2
0.716	Intermediate Similarity	NPD4139	Approved
0.7143	Intermediate Similarity	NPD4519	Discontinued
0.7143	Intermediate Similarity	NPD4623	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5693	Phase 1
0.7126	Intermediate Similarity	NPD6050	Approved
0.7126	Intermediate Similarity	NPD5281	Approved
0.7126	Intermediate Similarity	NPD5284	Approved
0.7126	Intermediate Similarity	NPD5694	Approved
0.7079	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4629	Approved
0.7079	Intermediate Similarity	NPD5210	Approved
0.7051	Intermediate Similarity	NPD7339	Approved
0.7051	Intermediate Similarity	NPD6942	Approved
0.7045	Intermediate Similarity	NPD4202	Approved
0.7037	Intermediate Similarity	NPD4695	Discontinued
0.7011	Intermediate Similarity	NPD5692	Phase 3
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5221	Approved
0.6988	Remote Similarity	NPD4788	Approved
0.6966	Remote Similarity	NPD6001	Approved
0.6923	Remote Similarity	NPD6084	Phase 2
0.6923	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD3573	Approved
0.6835	Remote Similarity	NPD4190	Phase 3
0.6835	Remote Similarity	NPD5275	Approved
0.6818	Remote Similarity	NPD4096	Approved
0.6813	Remote Similarity	NPD4697	Phase 3
0.6782	Remote Similarity	NPD4518	Approved
0.6778	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5286	Approved
0.6774	Remote Similarity	NPD5285	Approved
0.6774	Remote Similarity	NPD4696	Approved
0.6753	Remote Similarity	NPD7144	Approved
0.6753	Remote Similarity	NPD7143	Approved
0.6753	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6939	Phase 2
0.6739	Remote Similarity	NPD4755	Approved
0.6703	Remote Similarity	NPD5695	Phase 3
0.6702	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD5133	Approved
0.6632	Remote Similarity	NPD5091	Approved
0.6632	Remote Similarity	NPD5225	Approved
0.6632	Remote Similarity	NPD5224	Approved
0.6632	Remote Similarity	NPD5226	Approved
0.6632	Remote Similarity	NPD5211	Phase 2
0.6632	Remote Similarity	NPD4633	Approved
0.6628	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6923	Approved
0.6623	Remote Similarity	NPD6922	Approved
0.6596	Remote Similarity	NPD4700	Approved
0.6585	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5174	Approved
0.6562	Remote Similarity	NPD6052	Approved
0.6562	Remote Similarity	NPD5175	Approved
0.6556	Remote Similarity	NPD7515	Phase 2
0.6543	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6614	Approved
0.6522	Remote Similarity	NPD5654	Approved
0.6517	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5141	Approved
0.6494	Remote Similarity	NPD5360	Phase 3
0.6494	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6899	Approved
0.6465	Remote Similarity	NPD6881	Approved
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6429	Remote Similarity	NPD7525	Registered
0.6413	Remote Similarity	NPD7748	Approved
0.6413	Remote Similarity	NPD7900	Approved
0.6413	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4754	Approved
0.6383	Remote Similarity	NPD5959	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6337	Remote Similarity	NPD6883	Approved
0.6337	Remote Similarity	NPD7290	Approved
0.6337	Remote Similarity	NPD7102	Approved
0.6333	Remote Similarity	NPD6051	Approved
0.6329	Remote Similarity	NPD4789	Approved
0.6316	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5168	Approved
0.63	Remote Similarity	NPD4729	Approved
0.63	Remote Similarity	NPD6011	Approved
0.63	Remote Similarity	NPD4730	Approved
0.63	Remote Similarity	NPD7320	Approved
0.6296	Remote Similarity	NPD6926	Approved
0.6296	Remote Similarity	NPD6924	Approved
0.6279	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6650	Approved
0.6275	Remote Similarity	NPD6847	Approved
0.6275	Remote Similarity	NPD6649	Approved
0.6275	Remote Similarity	NPD6869	Approved
0.6275	Remote Similarity	NPD6617	Approved
0.6275	Remote Similarity	NPD8130	Phase 1
0.6265	Remote Similarity	NPD6932	Approved
0.6263	Remote Similarity	NPD6008	Approved
0.6263	Remote Similarity	NPD4768	Approved
0.6263	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6404	Discontinued
0.625	Remote Similarity	NPD6081	Approved
0.625	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6012	Approved
0.6238	Remote Similarity	NPD6373	Approved
0.6238	Remote Similarity	NPD6013	Approved
0.6238	Remote Similarity	NPD6372	Approved
0.6238	Remote Similarity	NPD6014	Approved
0.6234	Remote Similarity	NPD7331	Phase 2
0.6234	Remote Similarity	NPD4224	Phase 2
0.6214	Remote Similarity	NPD8297	Approved
0.6214	Remote Similarity	NPD6882	Approved
0.6212	Remote Similarity	NPD345	Approved
0.6212	Remote Similarity	NPD344	Approved
0.6212	Remote Similarity	NPD343	Approved
0.6211	Remote Similarity	NPD3495	Discontinued
0.6211	Remote Similarity	NPD7902	Approved
0.62	Remote Similarity	NPD5701	Approved
0.62	Remote Similarity	NPD6412	Phase 2
0.6196	Remote Similarity	NPD8035	Phase 2
0.6196	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD7145	Approved
0.6176	Remote Similarity	NPD5251	Approved
0.6176	Remote Similarity	NPD4634	Approved
0.6176	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5249	Phase 3
0.6176	Remote Similarity	NPD5250	Approved
0.6176	Remote Similarity	NPD5135	Approved
0.6176	Remote Similarity	NPD5169	Approved
0.6176	Remote Similarity	NPD5247	Approved
0.6176	Remote Similarity	NPD5248	Approved
0.6145	Remote Similarity	NPD6933	Approved
0.6139	Remote Similarity	NPD5128	Approved
0.6125	Remote Similarity	NPD4244	Approved
0.6125	Remote Similarity	NPD4245	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