NPASS Compound

Natural Product: NPC479457

Natural Product ID	NPC479457
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FOUGEXPKDJWRQY-SBCWIVKNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 69 72 0 0 0 0 0 0 0 0999 V2000 -3.5110 -2.4642 0.6542 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9331 -1.5747 -0.0979 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2757 -1.9519 -1.3926 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8332 -1.4660 -1.3193 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5761 -1.0539 0.1209 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3369 0.1196 0.5850 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9382 1.4627 0.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2232 0.1588 2.1198 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2295 0.2006 2.5278 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0189 -0.9267 1.9605 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8706 -1.1350 0.4764 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3126 -2.5936 0.2396 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7850 -0.3337 -0.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3662 0.3128 -1.3145 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1134 -0.3082 -0.0189 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1026 0.4125 -0.7105 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6576 1.4480 0.2368 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1538 1.2322 0.1842 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2139 -0.2167 -0.3185 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5259 -0.4197 -1.0712 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5953 0.5343 -2.0609 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1452 -0.3506 -1.1678 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7288 1.2358 1.4539 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2734 2.7289 -0.0610 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8325 -0.1406 0.2601 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2597 0.6750 -0.8956 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6403 0.5562 -1.4048 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7662 0.9972 -0.5922 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5688 2.0062 -0.9755 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6179 2.2388 0.0295 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4213 1.2519 0.9833 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 0.4975 0.6416 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8699 -0.4410 1.3759 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5357 -3.5328 0.3568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9907 -2.2826 1.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3180 -3.0797 -1.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7909 -1.5979 -2.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2035 -2.3775 -1.4815 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5896 -0.6966 -2.0593 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0290 -1.9294 0.7061 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6350 2.1932 0.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0555 1.7819 0.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9903 1.6451 -0.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6542 -0.7748 2.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7266 1.0335 2.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7270 1.1525 2.3508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2290 0.0553 3.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8592 -1.8903 2.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0971 -0.6872 2.1279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5435 -3.3029 0.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6823 -2.7296 -0.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1978 -2.7398 0.8927 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6005 0.9502 -1.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3556 1.2347 1.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6701 1.9203 -0.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1228 -0.9047 0.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3352 -0.2798 -0.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5347 -1.4569 -1.4273 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7041 0.9388 -2.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3418 0.4721 1.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1692 3.2601 0.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3519 0.1559 1.1751 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0373 1.7799 -0.7437 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5943 0.4701 -1.8103 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8250 -0.5230 -1.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6419 1.0945 -2.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4485 2.5629 -1.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4768 3.2718 0.4177 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5960 2.1202 -0.4810 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 6 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 19 22 1 0 18 23 1 0 17 24 1 0 6 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 25 2 1 0 32 28 1 0 11 5 1 0 22 16 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 1 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 16 53 1 6 17 54 1 1 18 55 1 6 19 56 1 1 20 57 1 0 20 58 1 0 21 59 1 0 23 60 1 0 24 61 1 0 25 62 1 1 26 63 1 0 26 64 1 0 27 65 1 0 27 66 1 0 29 67 1 0 30 68 1 0 30 69 1 0 M END

Standard InCHIKey	FOUGEXPKDJWRQY-SBCWIVKNSA-N
Standard InCHI	InChI=1S/C25H36O8/c1-14-5-8-18-24(2,16(14)7-6-15-9-12-31-21(15)29)10-4-11-25(18,3)23(30)33-22-20(28)19(27)17(13-26)32-22/h9,16-20,22,26-28H,1,4-8,10-13H2,2-3H3/t16-,17-,18+,19-,20+,22-,24+,25-/m0/s1
SMILES	C=C1CC[C@@H]2[C@](C)(CCC[C@]2(C)C(=O)O[C@H]2[C@@H]([C@H]([C@H](CO)O2)O)O)[C@H]1CCC1=CCOC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	464.24	Volume:	466.506 ? Van der Waals volume.
Dense:	0.995	LogP:	1.463 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.908 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.325 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	24.0
TPSA:	122.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.403	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.855	Fsp³:	0.76
MCE-18:	73.818 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.78	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.169	Promiscuous compounds:	0.044

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.889	MDCK Permeability:	-5.193
Pgp-inhibitor:	0.248	Pgp-substrate:	0.0
PAMPA:	0.377 ? 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):	0.011
20% Bioavailability (F20%):	0.157	30% Bioavailability (F30%):	0.601
50% Bioavailability (F50%):	0.663

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797	MRP1:	0.594
Plasma Protein Binding (PPB):	80.862%	Volume Distribution (VD):	-0.335
Fu:	12.741% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.002
BSEP inhibitor:	0.933

ADMET: Metabolism

CYP1A2-inhibitor:	0.879	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.496	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.027	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.988	CYP3A4-substrate:	0.318
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.983
HLM stability:	0.939 ? 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):

4.255

Half-life (T1/2):

1.157

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.273
Human Hepatotoxicity (H-HT):	0.679	Drug-induced Liver Injury (DILI):	0.633
AMES Toxicity:	0.757	Rat Oral Acute Toxicity:	0.29
Maximum Recommended Daily Dose:	0.328	Skin Sensitization:	1.0
Carcinogencity:	0.649	Eye Corrosion:	0.0
Eye Irritation:	0.09	Respiratory Toxicity:	0.041
Drug-induced Neurotoxicity:	0.118	Ototoxicity:	0.75
Hematotoxicity:	0.345	Drug-induced Nephrotoxicity:	0.951
Genotoxicity:	0.945	RPMI-8226 Immunitoxicity:	0.199
A549 Cytotoxicity:	0.332	Hek293 Cytotoxicity:	0.236
BCF:	1.251 ? 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:	4.23 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.841 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.049 ? 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
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21953622]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32520551]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10906	Pinus koraiensis	Species	Pinaceae	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	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
Activity	3
IC50	1

Activity Type	# Activity
Cell line	4

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
NPT34	Cell line	BV-2	Mus musculus	Activity	=	69.3	%	PMID[32520551]
NPT34	Cell line	BV-2	Mus musculus	IC50	>	500000.0	nM	PMID[32520551]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	93.3	%	PMID[32520551]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	112.5	%	PMID[32520551]

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 NPC479457 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	16295
0.1-0.2	26196
0.2-0.3	6925
0.3-0.4	372
0.4-0.5	47
0.5-0.6	4
0.6-0.7	16
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8923	High Similarity	NPC479461
0.7083	Intermediate Similarity	NPC479462
0.7027	Intermediate Similarity	NPC479453
0.6986	Remote Similarity	NPC479456
0.6849	Remote Similarity	NPC479455
0.6849	Remote Similarity	NPC479454
0.6806	Remote Similarity	NPC479459
0.6806	Remote Similarity	NPC479458
0.6757	Remote Similarity	NPC479452
0.6757	Remote Similarity	NPC479451
0.6712	Remote Similarity	NPC392
0.6712	Remote Similarity	NPC177524
0.6712	Remote Similarity	NPC219900
0.6667	Remote Similarity	NPC200513
0.625	Remote Similarity	NPC106416
0.625	Remote Similarity	NPC86316
0.625	Remote Similarity	NPC609165
0.6133	Remote Similarity	NPC599990
0.6104	Remote Similarity	NPC479460
0.597	Remote Similarity	NPC139692
0.5758	Remote Similarity	NPC608380
0.5362	Remote Similarity	NPC51486
0.5244	Remote Similarity	NPC484732

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479457 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6341
0.1-0.2	2686
0.2-0.3	118
0.3-0.4	1
0.4-0.5	2
0.5-0.6	0
0.6-0.7	2
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
0.6712	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)

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