NPASS Compound

Natural Product: NPC73061

Natural Product ID	NPC73061
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1,3-Dihydroxy-2-Formylanthraquinone
IUPAC Name	1,3-dihydroxy-9,10-dioxoanthracene-2-carbaldehyde
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2297225
PubChem CID	160712
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

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 28 30 0 0 0 0 0 0 0 0999 V2000 -4.4581 0.0628 -0.3492 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1734 -1.2896 -0.4048 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8642 -1.7252 -0.3421 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7957 -0.8568 -0.2236 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0834 0.4938 -0.1683 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3936 0.9310 -0.2309 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9569 1.4123 -0.0431 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2235 2.6444 0.0070 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4310 0.9682 0.0243 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4926 1.8538 0.1433 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8027 1.4408 0.2073 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0523 0.0950 0.1498 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4349 -0.3989 0.2142 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6906 -1.6186 0.1639 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0137 -0.8055 0.0315 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6937 -0.3973 -0.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4187 -1.3346 -0.1587 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1555 -2.5642 -0.2090 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3059 -2.1655 -0.0241 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8734 2.3094 0.3261 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4835 0.3753 -0.3999 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9974 -1.9989 -0.4984 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6397 -2.7882 -0.3858 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6224 1.9868 -0.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2834 2.8963 0.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2494 0.3006 0.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9813 -2.7259 0.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9609 2.8989 1.1353 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 2 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 12 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 15 19 1 0 11 20 1 0 6 1 1 0 16 9 1 0 17 4 1 0 1 21 1 0 2 22 1 0 3 23 1 0 6 24 1 0 10 25 1 0 13 26 1 0 19 27 1 0 20 28 1 0 M END

Standard InCHIKey	NSGZEHPFOUCUHD-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C15H8O5/c16-6-10-11(17)5-9-12(15(10)20)14(19)8-4-2-1-3-7(8)13(9)18/h1-6,17,20H
SMILES	c1ccc2c(c1)C(=O)c1cc(c(C=O)c(c1C2=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	268.04	Volume:	262.55 ? Van der Waals volume.
Dense:	1.021	LogP:	3.911 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.347 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.227 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	19.0
TPSA:	91.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.655	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.438	Fsp³:	0.0
MCE-18:	36.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	1
Colloidal aggregators:	0.369	Fluc inhibitor:	0.498 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.23 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.685 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.78	Promiscuous compounds:	0.259

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.974	MDCK Permeability:	-4.741
Pgp-inhibitor:	0.837	Pgp-substrate:	0.023
PAMPA:	0.919 ? 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):	0.218
20% Bioavailability (F20%):	0.003	30% Bioavailability (F30%):	0.339
50% Bioavailability (F50%):	0.733

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.608
Plasma Protein Binding (PPB):	96.059%	Volume Distribution (VD):	0.113
Fu:	4.533% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.924
OATP1B3 inhibitor:	0.98	BCRP inhibitor:	0.028
BSEP inhibitor:	0.138

ADMET: Metabolism

CYP1A2-inhibitor:	0.988	CYP1A2-substrate:	0.558
CYP2C19-inhibitor:	0.044	CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.252
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.989
HLM stability:	0.36 ? 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):

2.587

Half-life (T1/2):

1.355

ADMET: Toxicity

hERG Blockers:	0.06	hERG Blockers (10um):	0.616
Human Hepatotoxicity (H-HT):	0.574	Drug-induced Liver Injury (DILI):	0.809
AMES Toxicity:	0.777	Rat Oral Acute Toxicity:	0.364
Maximum Recommended Daily Dose:	0.408	Skin Sensitization:	0.959
Carcinogencity:	0.693	Eye Corrosion:	0.092
Eye Irritation:	0.998	Respiratory Toxicity:	0.876
Drug-induced Neurotoxicity:	0.31	Ototoxicity:	0.184
Hematotoxicity:	0.338	Drug-induced Nephrotoxicity:	0.174
Genotoxicity:	0.725	RPMI-8226 Immunitoxicity:	0.124
A549 Cytotoxicity:	0.771	Hek293 Cytotoxicity:	0.468
BCF:	1.655 ? 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:	4.366 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.515 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.184 ? 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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0168-1656(02)00067-6]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO12611	Lonicera korolkovii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520235]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1254564]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855442]
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192236]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26048790]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26195800]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36014413]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8626242]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21767	Rubia iberica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13446	Stachys recta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15917	Monilinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12611	Lonicera korolkovii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3376	Eriostemon brucei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO861	Siphonaria funiculata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10807	Melanothamnus somalensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28134	Coprosma lineariifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21767	Rubia iberica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28134	Coprosma lineariifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21767	Rubia iberica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15917	Monilinia fructigena	Species	Sclerotiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26859	Solanum curtipes	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2644	Portulaca pilosa	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13324	Euphorbia ingens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26587	Croton steenkampianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11827	Zerynthia polyxena	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10807	Melanothamnus somalensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23622	Pseudomonas putida	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2868	Perna viridis	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6430	Cercosporina kikuchii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO861	Siphonaria funiculata	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21767	Rubia iberica	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13446	Stachys recta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26764	Morinda tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10967	Parmelia gigas	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12611	Lonicera korolkovii	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11305	Garcinia cantleyana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18675	Pteris aquilina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3376	Eriostemon brucei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11734	Chara corallina	Species	Characeae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7626	Damnacanthus major	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7106	Talaromyces helicus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3011	Rubia wallichiana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15699	Damnacanthus indicus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6050	Hymenodictyon excelsum	Species	Rubiaceae	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
IC50	4

Activity Type	# Activity
Cell line	3
Non-molecular	1

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
NPT90	Cell line	DU-145	Homo sapiens	IC50	=	42000.0	nM	DOI[10.1007/s00044-012-0197-5]
NPT2844	Cell line	MES-SA	Homo sapiens	IC50	=	18000.0	nM	DOI[10.1007/s00044-012-0197-5]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	36000.0	nM	DOI[10.1007/s00044-012-0197-5]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	40000.0	nM	DOI[10.1007/s00044-012-0197-5]

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 NPC73061 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	25263
0.1-0.2	21519
0.2-0.3	2814
0.3-0.4	213
0.4-0.5	26
0.5-0.6	17
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
0.7059	Intermediate Similarity	NPC53206
0.6286	Remote Similarity	NPC142956
0.6154	Remote Similarity	NPC193703
0.6111	Remote Similarity	NPC44437
0.5946	Remote Similarity	NPC203063
0.5758	Remote Similarity	NPC96915
0.5758	Remote Similarity	NPC602077
0.5714	Remote Similarity	NPC300274
0.561	Remote Similarity	NPC208806
0.5526	Remote Similarity	NPC31799
0.5526	Remote Similarity	NPC608942
0.5385	Remote Similarity	NPC93015
0.5385	Remote Similarity	NPC609943
0.5366	Remote Similarity	NPC312338
0.5278	Remote Similarity	NPC120545
0.5263	Remote Similarity	NPC294226
0.525	Remote Similarity	NPC136588
0.5172	Remote Similarity	NPC19256
0.5128	Remote Similarity	NPC258502
0.5122	Remote Similarity	NPC53414
0.5122	Remote Similarity	NPC607416

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC73061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3551
0.1-0.2	5211
0.2-0.3	374
0.3-0.4	13
0.4-0.5	1
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