NPASS Compound

Structure

NPC91920 OpenBabel06302216202D 50 54 0 0 1 0 0 0 0 0999 V2000 13.6045 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6045 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7542 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9039 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0536 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2034 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3531 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5028 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6525 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8022 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9520 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1017 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2514 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8503 1.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8503 -0.4909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8503 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8503 -1.4727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8503 -2.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 -0.4909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7006 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5508 -0.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5508 -1.4727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2514 -0.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 -1.9636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7006 -2.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 -3.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5508 -3.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4011 -2.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2514 -3.4364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2514 -4.4182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4011 -4.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1017 -4.9091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1017 -5.8909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9520 -4.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9520 -3.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1017 -2.9455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9520 -2.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1017 -1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2514 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4011 -1.9636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4011 -0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4909 0.8503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4909 0.8503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 19 18 1 1 0 0 0 19 20 1 0 0 0 0 19 47 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 21 50 1 6 0 0 0 22 29 1 0 0 0 0 22 23 1 1 0 0 0 22 24 1 0 0 0 0 24 25 1 1 0 0 0 24 47 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 27 45 1 0 0 0 0 27 28 1 1 0 0 0 27 29 1 0 0 0 0 29 30 1 1 0 0 0 30 31 2 0 0 0 0 30 32 1 0 0 0 0 32 33 2 0 0 0 0 33 45 1 0 0 0 0 34 33 1 6 0 0 0 34 35 1 0 0 0 0 34 41 1 0 0 0 0 35 36 1 1 0 0 0 35 37 1 0 0 0 0 37 38 1 6 0 0 0 37 39 1 0 0 0 0 39 40 1 0 0 0 0 40 41 1 0 0 0 0 41 42 1 1 0 0 0 41 43 1 0 0 0 0 43 44 1 0 0 0 0 44 45 1 0 0 0 0 45 46 1 6 0 0 0 47 48 1 0 0 0 0 47 49 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.22
Volume:	388.427
LogP:	5.426
LogD:	4.219
LogS:	-3.975
# Rotatable Bonds:	8
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	3.164
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.919
MDCK Permeability:	2.8406348064891063e-05
Pgp-inhibitor:	0.938
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.554

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.216
Plasma Protein Binding (PPB):	98.55104064941406%
Volume Distribution (VD):	1.704
Pgp-substrate:	0.8567915558815002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.635
CYP1A2-substrate:	0.647
CYP2C19-inhibitor:	0.789
CYP2C19-substrate:	0.43
CYP2C9-inhibitor:	0.846
CYP2C9-substrate:	0.98
CYP2D6-inhibitor:	0.745
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	15.072
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.812
Drug-inuced Liver Injury (DILI):	0.125
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.949
Carcinogencity:	0.647
Eye Corrosion:	0.032
Eye Irritation:	0.917
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC91920

Natural Product ID:	NPC91920
*Common Name:**	DCFFXRHWUWIAHM-XVLYEGEHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DCFFXRHWUWIAHM-XVLYEGEHSA-N
Standard InCHI:	InChI=1S/C46H78O4/c1-10-11-12-13-14-15-16-17-18-19-20-21-22-23-39(49)50-38-31-37(48)46(9)36(42(38,4)5)25-27-45(8)41(46)35(47)30-34-40-33(3)32(2)24-26-43(40,6)28-29-44(34,45)7/h30,32-33,36-38,40-41,48H,10-29,31H2,1-9H3/t32-,33+,36+,37+,38+,40+,41+,43-,44-,45-,46-/m1/s1
SMILES:	CCCCCCCCCCCCCCCC(=O)O[C@H]1C[C@@H]([C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2C(=O)C=C2[C@@H]4[C@@H](C)[C@H](C)CC[C@]4(C)CC[C@@]32C)C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	54753312
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO25738	Tanacetum praeteritum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO16741.1	Codonopsis pilosula var. modesta	Varieties	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16741.1	Codonopsis pilosula var. modesta	Varieties	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26102	Aconitum campylorrhynchum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26102	Aconitum campylorrhynchum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26102	Aconitum campylorrhynchum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26924	Sphaerella asteroma	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26404	Aspergillus multicolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9292	Chalina arbuscula	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25738	Tanacetum praeteritum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741.1	Codonopsis pilosula var. modesta	Varieties	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25994	Heliotropium glutinosum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26347	Narcissus triandrus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21441	Microglossa zeylanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26051	Osmitopsis osmitoides	Species	Asteraceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC91920 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	234
0.1-0.2	1491
0.2-0.3	4642
0.3-0.4	9120
0.4-0.5	12515
0.5-0.6	6312
0.6-0.7	4849
0.7-0.8	2759
0.8-0.85	515
0.85-0.9	232
0.9-0.95	26
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID

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 NPC91920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1771
0.2-0.3	3776
0.3-0.4	2217
0.4-0.5	707
0.5-0.6	224
0.6-0.7	159
0.7-0.8	83
0.8-0.85	2
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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