NPASS Compound

Natural Product: NPC287926

Natural Product ID	NPC287926
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KBIHHHDCLJQNHG-RNOWOOBNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	13870581
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

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 53 55 0 0 0 0 0 0 0 0999 V2000 3.1230 0.7764 2.0446 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8487 0.0772 2.1062 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6326 0.8379 1.5591 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3048 2.0364 2.3755 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3842 -0.2948 1.7614 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5501 -0.1640 0.9056 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7699 0.9955 0.2049 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8934 1.0910 -0.6049 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7884 0.0415 -0.7151 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5751 -1.1167 -0.0194 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4461 -1.1973 0.7871 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4814 -2.1702 -0.1355 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3095 -3.3887 0.5630 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9305 0.1277 -1.5330 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1333 2.2427 -1.3155 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2368 3.3438 -1.2340 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2963 -1.4932 1.6642 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6532 -1.1956 1.3848 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8356 -1.2348 -0.0518 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3200 -2.3428 -0.7229 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4203 -2.4995 -2.0858 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0576 -1.5188 -2.8162 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5844 -0.4046 -2.2041 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4601 -0.2851 -0.8152 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2178 0.5667 -2.9465 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7698 1.7182 -2.3737 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1317 -1.7263 -4.1888 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1392 1.7938 1.6044 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9106 0.0960 1.6412 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4907 0.9595 3.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5923 -0.1143 3.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7276 1.0677 0.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6876 2.9492 1.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7485 2.1394 2.6602 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8973 2.0051 3.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6997 -0.1981 2.8393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1231 1.8649 0.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3141 -2.1308 1.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0048 -3.2442 1.6139 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2526 -3.9742 0.5010 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5065 -3.9633 0.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5466 0.9075 -1.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1198 3.6122 -0.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6567 4.2442 -1.7234 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2254 3.0841 -1.6094 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2590 -2.0198 1.8497 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8046 -3.1452 -0.1709 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0034 -3.3855 -2.5889 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8934 0.6160 -0.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9765 2.4728 -2.1056 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3653 1.5489 -1.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4291 2.2468 -3.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8645 -2.2553 -4.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 3 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 9 14 1 0 8 15 1 0 15 16 1 0 5 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 22 27 1 0 18 2 1 0 24 19 1 0 11 6 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 1 3 32 1 6 4 33 1 0 4 34 1 0 4 35 1 0 5 36 1 1 7 37 1 0 11 38 1 0 13 39 1 0 13 40 1 0 13 41 1 0 14 42 1 0 16 43 1 0 16 44 1 0 16 45 1 0 18 46 1 1 20 47 1 0 21 48 1 0 24 49 1 0 26 50 1 0 26 51 1 0 26 52 1 0 27 53 1 0 M END

Standard InCHIKey	KBIHHHDCLJQNHG-RNOWOOBNSA-N
Standard InCHI	InChI=1S/C21H26O6/c1-11-12(2)21(14-9-17(25-4)19(23)18(10-14)26-5)27-20(11)13-6-7-15(22)16(8-13)24-3/h6-12,20-23H,1-5H3/t11-,12-,20+,21-/m0/s1
SMILES	C[C@H]1[C@H](C)[C@@H](c2cc(c(c(c2)OC)O)OC)O[C@H]1c1ccc(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	374.17	Volume:	383.025 ? Van der Waals volume.
Dense:	0.977	LogP:	1.884 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.102 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.555 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	17.0
TPSA:	77.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.816	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.488	Fsp³:	0.429
MCE-18:	65.333 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.142	Fluc inhibitor:	0.371 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.054 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.328	Promiscuous compounds:	0.246

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.303	MDCK Permeability:	-4.886
Pgp-inhibitor:	0.77	Pgp-substrate:	0.177
PAMPA:	0.006 ? 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):	0.01
20% Bioavailability (F20%):	0.241	30% Bioavailability (F30%):	0.073
50% Bioavailability (F50%):	0.886

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075	MRP1:	0.982
Plasma Protein Binding (PPB):	89.278%	Volume Distribution (VD):	-0.247
Fu:	10.133% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.993	BCRP inhibitor:	0.66
BSEP inhibitor:	0.832

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.461
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.993
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.003 ? 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):

9.731

Half-life (T1/2):

1.657

ADMET: Toxicity

hERG Blockers:	0.139	hERG Blockers (10um):	0.479
Human Hepatotoxicity (H-HT):	0.744	Drug-induced Liver Injury (DILI):	0.781
AMES Toxicity:	0.509	Rat Oral Acute Toxicity:	0.429
Maximum Recommended Daily Dose:	0.319	Skin Sensitization:	0.703
Carcinogencity:	0.589	Eye Corrosion:	0.043
Eye Irritation:	0.813	Respiratory Toxicity:	0.83
Drug-induced Neurotoxicity:	0.451	Ototoxicity:	0.389
Hematotoxicity:	0.517	Drug-induced Nephrotoxicity:	0.388
Genotoxicity:	0.556	RPMI-8226 Immunitoxicity:	0.236
A549 Cytotoxicity:	0.653	Hek293 Cytotoxicity:	0.564
BCF:	1.249 ? 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:	3.845 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.85 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.296 ? 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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32515616]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33444950]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO490	Lophozonia menziesii	Species	Nothofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7237	Xanthostemon oppositifolius	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28409	Lens phaseoloides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8532	Helipterum tenellum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1382	Hyptis tomentosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6113	Piper pedicellosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5162	Comaster multifida	Species	Comatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19928	Lachnoanaerobaculum saburreum	Species	Lachnospiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4539	Ipomoea cristulata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO490	Lophozonia menziesii	Species	Nothofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17811	Cephalonoplos segetum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5746	Pancratium trianthum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7393	Esenbeckia nesiotica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5334	Rhodotypos scandens	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2665	Andinobates fulguritus	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8303	Catalpa bignonioides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5241	Myristica fragrans	Species	Myristicaceae	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

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

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 NPC287926 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	20995
0.1-0.2	23266
0.2-0.3	4751
0.3-0.4	616
0.4-0.5	161
0.5-0.6	33
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC282703
0.8947	High Similarity	NPC184733
0.8947	High Similarity	NPC128208
0.8947	High Similarity	NPC129570
0.8947	High Similarity	NPC63238
0.8947	High Similarity	NPC602603
0.7556	Intermediate Similarity	NPC11258
0.7556	Intermediate Similarity	NPC21867
0.7556	Intermediate Similarity	NPC487683
0.7556	Intermediate Similarity	NPC45774
0.7556	Intermediate Similarity	NPC74914
0.7234	Intermediate Similarity	NPC488986
0.7111	Intermediate Similarity	NPC158331
0.6977	Remote Similarity	NPC204215
0.6957	Remote Similarity	NPC126409
0.6957	Remote Similarity	NPC99572
0.6818	Remote Similarity	NPC242807
0.6818	Remote Similarity	NPC153739
0.68	Remote Similarity	NPC142547
0.68	Remote Similarity	NPC228469
0.6444	Remote Similarity	NPC142985
0.6087	Remote Similarity	NPC115207
0.6087	Remote Similarity	NPC158079
0.6087	Remote Similarity	NPC228346
0.6087	Remote Similarity	NPC40432
0.6087	Remote Similarity	NPC161557
0.6042	Remote Similarity	NPC147379
0.6042	Remote Similarity	NPC469480
0.5909	Remote Similarity	NPC244983
0.5862	Remote Similarity	NPC77861
0.56	Remote Similarity	NPC487684
0.55	Remote Similarity	NPC487682
0.5439	Remote Similarity	NPC282833
0.5306	Remote Similarity	NPC326095
0.5283	Remote Similarity	NPC27843
0.5283	Remote Similarity	NPC478955
0.5283	Remote Similarity	NPC478700
0.5283	Remote Similarity	NPC7171
0.5273	Remote Similarity	NPC488988
0.5238	Remote Similarity	NPC176730
0.5238	Remote Similarity	NPC123175
0.5217	Remote Similarity	NPC141765
0.5217	Remote Similarity	NPC34103
0.5208	Remote Similarity	NPC209567
0.52	Remote Similarity	NPC175067
0.5172	Remote Similarity	NPC486558
0.5172	Remote Similarity	NPC470095
0.5116	Remote Similarity	NPC9891
0.5116	Remote Similarity	NPC88297
0.5116	Remote Similarity	NPC186845
0.5111	Remote Similarity	NPC216929
0.5111	Remote Similarity	NPC159418
0.5111	Remote Similarity	NPC312713
0.5111	Remote Similarity	NPC126935
0.5111	Remote Similarity	NPC65933
0.5111	Remote Similarity	NPC57268
0.5111	Remote Similarity	NPC172676
0.5098	Remote Similarity	NPC470804
0.5091	Remote Similarity	NPC135777
0.5091	Remote Similarity	NPC223185
0.5091	Remote Similarity	NPC610778

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC287926 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4075
0.1-0.2	4859
0.2-0.3	204
0.3-0.4	9
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
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
		NPD

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