NPASS Compound

Natural Product: NPC13779

Natural Product ID	NPC13779
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Petalostemumol G
IUPAC Name	2-[3,4-dihydroxy-2,6-bis(3-methylbut-2-enyl)phenyl]-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms	Petalostemumol G
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL515360
PubChem CID	5480298
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003587] 2'-prenylated flavones

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 71 73 0 0 0 0 0 0 0 0999 V2000 -3.7447 -4.6734 -0.4707 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7670 -4.3530 0.9822 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9905 -3.4805 1.5796 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9443 -2.6565 0.8934 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2378 -1.2099 0.9629 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3414 -0.8711 1.7461 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6245 0.4392 1.9660 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7205 0.7874 2.7451 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8390 1.4122 1.4265 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7352 1.0710 0.6402 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4127 -0.2669 0.3901 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3394 -0.5909 -0.5384 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9058 -0.2000 -0.3082 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9303 -0.4358 -1.0796 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2060 0.0283 -0.7340 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3332 0.7943 0.5278 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6691 1.4398 0.6383 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5129 1.1619 1.6238 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8360 1.8219 1.7044 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 0.1639 2.6546 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3019 -0.2047 -1.5230 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5799 0.2523 -1.1882 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1047 -0.9290 -2.6985 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8496 -1.3799 -3.0299 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7415 -1.1492 -2.2409 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4888 -1.6005 -2.5767 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3173 -2.2509 -3.6362 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5486 -1.3049 -1.7024 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8116 -1.7567 -2.0665 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6565 -2.0980 -4.1967 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9303 2.1803 0.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6302 2.8413 -1.0535 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8858 4.1401 -1.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6056 4.6996 -2.3295 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4899 5.1364 -0.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1863 2.7375 1.6942 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7709 -5.1008 1.7948 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6182 -4.1161 -0.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8162 -4.4439 -0.9844 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9895 -5.7672 -0.6074 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0805 -3.3238 2.6472 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0172 -2.8296 1.5625 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6505 -3.0860 -0.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9985 -1.6047 2.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5471 0.1739 2.6824 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1307 0.1757 1.4182 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5703 1.6253 0.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0036 2.1871 -0.0999 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2575 2.0703 0.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5608 1.1695 2.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7651 2.7634 2.3159 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8829 -0.8297 2.2470 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1956 0.5974 3.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8933 0.0785 3.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3021 -0.4233 -1.0393 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9733 -1.1190 -3.3318 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2904 -1.3160 -2.8366 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8789 -1.6314 -5.0724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6916 2.9389 0.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0162 1.7979 -0.2968 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9542 2.2057 -1.8858 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5726 5.1404 -2.0146 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8045 3.9372 -3.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9295 5.4640 -2.7900 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1557 6.0309 -0.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5599 4.7408 0.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4755 5.5148 -0.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0352 3.1210 1.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4915 -6.1306 2.0071 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9959 -4.5801 2.7468 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7215 -5.1262 1.1907 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 7 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 2 3 18 19 1 0 18 20 1 0 15 21 1 0 21 22 1 0 21 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 24 30 1 0 10 31 1 0 31 32 1 0 32 33 2 3 33 34 1 0 33 35 1 0 9 36 1 0 2 37 1 0 11 5 1 0 28 12 2 0 25 14 1 0 1 38 1 0 1 39 1 0 1 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 6 44 1 0 8 45 1 0 16 46 1 0 16 47 1 0 17 48 1 0 19 49 1 0 19 50 1 0 19 51 1 0 20 52 1 0 20 53 1 0 20 54 1 0 22 55 1 0 23 56 1 0 29 57 1 0 30 58 1 0 31 59 1 0 31 60 1 0 32 61 1 0 34 62 1 0 34 63 1 0 34 64 1 0 35 65 1 0 35 66 1 0 35 67 1 0 36 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 M END

Standard InCHIKey	JJYTVPNJUZEOPO-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C30H34O7/c1-15(2)7-10-18-13-23(33)26(34)20(12-9-17(5)6)24(18)30-28(36)27(35)25-22(32)14-21(31)19(29(25)37-30)11-8-16(3)4/h7-9,13-14,31-34,36H,10-12H2,1-6H3
SMILES	CC(=CCc1cc(O)c(c(c1c1oc2c(CC=C(C)C)c(O)cc(c2c(=O)c1O)O)CC=C(C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	506.23	Volume:	534.297 ? Van der Waals volume.
Dense:	0.947	LogP:	6.158 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.144 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.924 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	21.0
TPSA:	131.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.182	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.592	Fsp³:	0.3
MCE-18:	25.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.999	Fluc inhibitor:	0.457 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.958 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.644 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.573	Promiscuous compounds:	0.198

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.161	MDCK Permeability:	-4.755
Pgp-inhibitor:	0.083	Pgp-substrate:	0.063
PAMPA:	0.952 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.786
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.994
Plasma Protein Binding (PPB):	95.759%	Volume Distribution (VD):	0.067
Fu:	4.717% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	1.0
BSEP inhibitor:	0.042

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.523
CYP2D6-inhibitor:	0.5	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.081	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

7.079

Half-life (T1/2):

1.734

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.589
Human Hepatotoxicity (H-HT):	0.524	Drug-induced Liver Injury (DILI):	0.723
AMES Toxicity:	0.69	Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.594	Skin Sensitization:	0.996
Carcinogencity:	0.22	Eye Corrosion:	0.0
Eye Irritation:	0.091	Respiratory Toxicity:	0.994
Drug-induced Neurotoxicity:	0.074	Ototoxicity:	0.535
Hematotoxicity:	0.094	Drug-induced Nephrotoxicity:	0.629
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.71	Hek293 Cytotoxicity:	0.7
BCF:	2.044 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.629 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.411 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.08 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27127	Petalostemum purpureum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8289060]
NPO27127	Petalostemum purpureum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27127	Petalostemum purpureum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

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	Organism Name	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
MIC	6

Activity Type	# Activity
Organism	6

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	5.0	ug.mL-1	PMID[23738539]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	5.0	ug.mL-1	PMID[23738539]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	5.0	ug.mL-1	PMID[18056272]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	5.0	ug.mL-1	PMID[23738539]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug.mL-1	PMID[23738539]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	PMID[18056272]

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC13779 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	20726
0.1-0.2	26566
0.2-0.3	2285
0.3-0.4	222
0.4-0.5	47
0.5-0.6	4
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6562	Remote Similarity	NPC63187
0.6418	Remote Similarity	NPC59162
0.6324	Remote Similarity	NPC475799
0.6308	Remote Similarity	NPC9117
0.6176	Remote Similarity	NPC273538
0.6133	Remote Similarity	NPC273843
0.5942	Remote Similarity	NPC293053
0.52	Remote Similarity	NPC3980
0.507	Remote Similarity	NPC88804
0.5068	Remote Similarity	NPC601414

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC13779 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4062
0.1-0.2	5065
0.2-0.3	21
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6176	Remote Similarity	NPD4378	Phase 3

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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