NPASS Compound

Natural Product: NPC225888

Natural Product ID	NPC225888
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BHSMLHMTPPELTD-OAQYLSRUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101687163
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 5.0967 -0.6789 1.7383 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6522 0.1102 0.5478 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1100 1.5336 0.6044 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1634 0.0046 0.3353 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2931 0.8914 0.9173 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9233 0.7679 0.7022 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3790 -0.2257 -0.0887 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2667 -1.0885 -0.6501 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6525 -0.9755 -0.4403 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5421 -1.8668 -1.0228 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9298 -2.1313 -1.4567 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9161 -1.9962 -2.8561 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0514 -0.3483 -0.3042 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3090 0.0531 -1.7708 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6933 -1.6550 -0.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0663 -1.6964 -0.6664 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8813 -0.5020 -0.4784 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3667 0.5661 0.4086 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0065 1.8768 0.0054 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9062 0.2670 1.8174 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8851 0.6446 0.4669 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3491 1.5630 1.2189 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0898 1.7340 1.4154 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5585 2.6392 2.1390 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1491 2.4743 1.9088 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6459 0.0116 2.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8139 -1.4821 1.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 -1.1210 2.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1298 -0.3506 -0.3630 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5749 2.1258 -0.1812 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2032 1.5434 0.4037 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9582 1.9905 1.5972 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7130 1.6769 1.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7484 -1.7211 -2.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0573 -2.2588 -3.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1765 -0.9744 -3.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6425 -2.7073 -3.3404 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6444 -0.7895 -2.3764 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3711 0.4754 -2.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0257 0.9215 -1.8268 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7693 -1.8886 1.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1678 -2.5220 -0.5623 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 -2.0717 -1.7270 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6206 -2.5635 -0.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9316 -0.8321 -0.1517 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1262 -0.1041 -1.5242 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8970 1.6744 -0.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3384 2.5112 -0.6115 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4096 2.4369 0.8874 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9254 -0.1475 1.6717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0564 1.2161 2.3906 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3015 -0.4719 2.3406 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0988 3.4612 1.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 8 11 1 0 11 12 1 0 7 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 22 25 1 0 9 4 1 0 21 13 1 0 23 6 1 0 1 26 1 0 1 27 1 0 1 28 1 0 2 29 1 0 3 30 1 0 3 31 1 0 3 32 1 0 5 33 1 0 10 34 1 0 12 35 1 0 12 36 1 0 12 37 1 0 14 38 1 0 14 39 1 0 14 40 1 0 15 41 1 0 15 42 1 0 16 43 1 0 16 44 1 0 17 45 1 0 17 46 1 0 19 47 1 0 19 48 1 0 19 49 1 0 20 50 1 0 20 51 1 0 20 52 1 0 25 53 1 0 M END

Standard InCHIKey	BHSMLHMTPPELTD-OAQYLSRUSA-N
Standard InCHI	InChI=1S/C21H28O4/c1-11(2)12-10-13-14(18(25-6)16(12)23)21(5)9-7-8-20(3,4)19(21)17(24)15(13)22/h10-11,23-24H,7-9H2,1-6H3/t21-/m1/s1
SMILES	CC(C)c1cc2c(c(c1O)OC)[C@@]1(C)CCCC(C)(C)C1=C(C2=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	344.2	Volume:	368.081 ? Van der Waals volume.
Dense:	0.935	LogP:	3.208 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.704 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.008 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	17.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.792	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.737	Fsp³:	0.571
MCE-18:	79.273 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.303	Fluc inhibitor:	0.006 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.22 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.191 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.206	Promiscuous compounds:	0.073

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.763	MDCK Permeability:	-4.811
Pgp-inhibitor:	0.922	Pgp-substrate:	0.673
PAMPA:	0.055 ? 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):	0.023
20% Bioavailability (F20%):	0.876	30% Bioavailability (F30%):	0.978
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192	MRP1:	0.999
Plasma Protein Binding (PPB):	97.226%	Volume Distribution (VD):	-0.012
Fu:	2.469% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	0.957	BCRP inhibitor:	0.305
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.165	CYP2C19-substrate:	0.994
CYP2C9-inhibitor:	0.023	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.983
CYP3A4-inhibitor:	0.975	CYP3A4-substrate:	0.975
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	1.0
HLM stability:	0.311 ? 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):

5.819

Half-life (T1/2):

0.91

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.175
Human Hepatotoxicity (H-HT):	0.688	Drug-induced Liver Injury (DILI):	0.49
AMES Toxicity:	0.443	Rat Oral Acute Toxicity:	0.647
Maximum Recommended Daily Dose:	0.581	Skin Sensitization:	0.645
Carcinogencity:	0.77	Eye Corrosion:	0.011
Eye Irritation:	0.888	Respiratory Toxicity:	0.742
Drug-induced Neurotoxicity:	0.088	Ototoxicity:	0.605
Hematotoxicity:	0.662	Drug-induced Nephrotoxicity:	0.928
Genotoxicity:	0.767	RPMI-8226 Immunitoxicity:	0.109
A549 Cytotoxicity:	0.095	Hek293 Cytotoxicity:	0.297
BCF:	2.269 ? 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:	4.82 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.313 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.812 ? 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
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1397	Cylindrocarpon lucidum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1809	Delphinium scabriflorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9555	Aplysilla tango	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1397	Cylindrocarpon lucidum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1809	Delphinium scabriflorum	Species	Ranunculaceae	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 NPC225888 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	11679
0.1-0.2	36140
0.2-0.3	1957
0.3-0.4	64
0.4-0.5	11
0.5-0.6	4
0.6-0.7	3
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
0.6441	Remote Similarity	NPC230811
0.6333	Remote Similarity	NPC171460
0.623	Remote Similarity	NPC471670
0.5846	Remote Similarity	NPC29055
0.55	Remote Similarity	NPC4170
0.5385	Remote Similarity	NPC309169
0.5312	Remote Similarity	NPC606138

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC225888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3313
0.1-0.2	5788
0.2-0.3	49
0.3-0.4	0
0.4-0.5	0
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