NPASS Compound

Natural Product: NPC23871

Natural Product ID	NPC23871
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QTHZKQQTHZVUHQ-SFHVURJKSA-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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-prenylated flavanones

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 49 51 0 0 0 0 0 0 0 0999 V2000 -4.7092 2.6700 0.2189 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3646 2.2459 -0.2436 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1118 1.0078 -0.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7968 0.5148 -1.1113 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2867 -0.6126 -0.2680 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8089 -1.8824 -0.3851 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2993 -2.8827 0.4160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2886 -2.6437 1.3232 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2457 -1.3713 1.4513 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3141 -1.0716 2.3963 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9302 -2.0176 2.9529 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6185 0.3592 2.6515 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5646 1.1048 1.3639 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6559 0.7426 0.4576 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7377 0.0218 0.8905 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7926 -0.3376 0.0414 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7339 0.0495 -1.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6594 0.7796 -1.7529 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6370 1.1175 -0.8910 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6202 1.1612 -3.0848 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7440 -0.2711 -2.1709 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2840 0.9022 0.7908 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2722 -0.3812 0.6451 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2364 -3.6378 2.1374 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8366 -2.1254 -1.3076 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3778 -3.4274 -1.4331 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2628 3.2346 -0.2702 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6733 2.7607 1.3149 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8811 3.6938 -0.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5111 1.9819 -0.1294 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9429 0.3023 -0.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9024 0.1687 -2.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0502 1.3369 -1.1563 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7198 -3.8688 0.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5153 0.5250 3.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7687 0.7289 3.2942 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6404 2.1905 1.5905 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7932 -0.2884 1.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6391 -0.9130 0.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7779 1.6909 -1.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4927 1.3856 -3.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5360 0.3773 -2.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5874 -4.4819 1.7430 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5857 -4.0749 -1.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6267 -3.8157 -0.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2854 -3.3756 -2.0669 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6583 4.2259 -0.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4868 2.9724 0.4850 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7859 3.2285 -1.2727 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 2 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 17 21 1 0 13 22 1 0 22 23 1 0 8 24 1 0 6 25 1 0 25 26 1 0 2 27 1 0 23 5 1 0 23 9 2 0 19 14 1 0 1 28 1 0 1 29 1 0 1 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 7 34 1 0 12 35 1 0 12 36 1 0 13 37 1 1 15 38 1 0 16 39 1 0 19 40 1 0 20 41 1 0 21 42 1 0 24 43 1 0 26 44 1 0 26 45 1 0 26 46 1 0 27 47 1 0 27 48 1 0 27 49 1 0 M END

Standard InCHIKey	QTHZKQQTHZVUHQ-SFHVURJKSA-N
Standard InCHI	InChI=1S/C21H22O6/c1-11(2)4-6-13-19(26-3)10-17(25)20-16(24)9-18(27-21(13)20)12-5-7-14(22)15(23)8-12/h4-5,7-8,10,18,22-23,25H,6,9H2,1-3H3/t18-/m0/s1
SMILES	CC(=CCc1c(cc(c2C(=O)C[C@@H](c3ccc(c(c3)O)O)Oc12)O)OC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	370.14	Volume:	377.752 ? Van der Waals volume.
Dense:	0.98	LogP:	4.027 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.422 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.125 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	19.0
TPSA:	96.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.555	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.299	Fsp³:	0.286
MCE-18:	62.963 ? 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:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.769	Fluc inhibitor:	0.675 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.6 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.541 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.286	Promiscuous compounds:	0.144

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.967	MDCK Permeability:	-4.745
Pgp-inhibitor:	0.44	Pgp-substrate:	0.004
PAMPA:	0.029 ? 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):	0.016
20% Bioavailability (F20%):	0.936	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.929
Plasma Protein Binding (PPB):	95.312%	Volume Distribution (VD):	0.021
Fu:	4.396% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.969
BSEP inhibitor:	0.717

ADMET: Metabolism

CYP1A2-inhibitor:	0.018	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.238	CYP2C19-substrate:	0.971
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
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):

14.153

Half-life (T1/2):

1.625

ADMET: Toxicity

hERG Blockers:	0.099	hERG Blockers (10um):	0.588
Human Hepatotoxicity (H-HT):	0.776	Drug-induced Liver Injury (DILI):	0.801
AMES Toxicity:	0.8	Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.779	Skin Sensitization:	0.992
Carcinogencity:	0.361	Eye Corrosion:	0.001
Eye Irritation:	0.916	Respiratory Toxicity:	0.932
Drug-induced Neurotoxicity:	0.542	Ototoxicity:	0.795
Hematotoxicity:	0.223	Drug-induced Nephrotoxicity:	0.754
Genotoxicity:	0.986	RPMI-8226 Immunitoxicity:	0.056
A549 Cytotoxicity:	0.948	Hek293 Cytotoxicity:	0.485
BCF:	1.846 ? 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:	4.693 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.172 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.542 ? 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
NPO16662	Plumbago indica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s10529-015-1969-z]
NPO16662	Plumbago indica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jbiosc.2011.02.003]
NPO17812	Jatropha neopauciflora	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125233]
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17475486]
NPO21731	Acanthella cavernosa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2045823]
NPO4211	Negombata corticata	Species	Latrunculiidae	Eukaryota	n.a.	formosan	n.a.	PMID[20718475]
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21226490]
NPO17034	Panagrellus redivivus	Species	Panagrolaimidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23213209]
NPO16662	Plumbago indica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24200	Piper angustifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16887	Cordyline cannifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4211	Negombata corticata	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21731	Acanthella cavernosa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8889	Senecio gallicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21440	Trixis wrightii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23983	Siphonoglossa buchii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16412	Menyanthes trifoliata	Species	Menyanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15985	Iris bungei	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24739	Graphiopsis chlorocephala	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16412	Menyanthes trifoliata	Species	Menyanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16662	Plumbago indica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24200	Piper angustifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16662	Plumbago indica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24200	Piper angustifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16412	Menyanthes trifoliata	Species	Menyanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15985	Iris bungei	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16412	Menyanthes trifoliata	Species	Menyanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14151	Macaca fascicularis	Species	Cercopithecidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23661	Spiraea koreana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17812	Jatropha neopauciflora	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8889	Senecio gallicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24420	Aria japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15685	Paspalum dilatatum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24739	Graphiopsis chlorocephala	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21731	Acanthella cavernosa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4211	Negombata corticata	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16412	Menyanthes trifoliata	Species	Menyanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21440	Trixis wrightii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16662	Plumbago indica	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21430	Myctophum asperum	Species	Myctophidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13995	Siparuna macrotepala	Species	Siparunaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16887	Cordyline cannifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17133	Clathria reinwardti	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3703	Achillea ochroleuca	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6115	Primulina dryas	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16198	Parmelia quercina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14916	Pseudophryne australis	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23937	Notholaena pallens	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1871	Aristolochia durior	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13479	Flourensia riparia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4721	Amphiachyris dracunculoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6174	Croton malambo	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23983	Siphonoglossa buchii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24200	Piper angustifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23806	Polygala triphylla	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17273	Empedobacter haloabium	Species	Flavobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17034	Panagrellus redivivus	Species	Panagrolaimidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14495	Lindheimera texana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17298	Thamnophis butleri	Species	Colubridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10558	Vernonia wildii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15985	Iris bungei	Species	Iridaceae	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 NPC23871 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	18379
0.1-0.2	24754
0.2-0.3	5669
0.3-0.4	733
0.4-0.5	250
0.5-0.6	60
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8421	Intermediate Similarity	NPC220998
0.7049	Intermediate Similarity	NPC156190
0.6406	Remote Similarity	NPC610133
0.6061	Remote Similarity	NPC76338
0.6061	Remote Similarity	NPC250242
0.6	Remote Similarity	NPC328164
0.597	Remote Similarity	NPC291878
0.5915	Remote Similarity	NPC213896
0.5909	Remote Similarity	NPC480990
0.5846	Remote Similarity	NPC107572
0.5846	Remote Similarity	NPC32739
0.5758	Remote Similarity	NPC148757
0.5714	Remote Similarity	NPC35038
0.5672	Remote Similarity	NPC66515
0.5652	Remote Similarity	NPC161506
0.5645	Remote Similarity	NPC321011
0.5645	Remote Similarity	NPC294852
0.5645	Remote Similarity	NPC188679
0.5588	Remote Similarity	NPC125855
0.5588	Remote Similarity	NPC480158
0.5556	Remote Similarity	NPC484416
0.5541	Remote Similarity	NPC261063
0.5522	Remote Similarity	NPC69674
0.5522	Remote Similarity	NPC175504
0.5467	Remote Similarity	NPC321779
0.5455	Remote Similarity	NPC76372
0.5455	Remote Similarity	NPC37496
0.5441	Remote Similarity	NPC17170
0.5441	Remote Similarity	NPC109223
0.5441	Remote Similarity	NPC10937
0.5417	Remote Similarity	NPC125894
0.5417	Remote Similarity	NPC142405
0.5405	Remote Similarity	NPC479210
0.5397	Remote Similarity	NPC192083
0.5385	Remote Similarity	NPC259685
0.5373	Remote Similarity	NPC1089
0.5373	Remote Similarity	NPC39329
0.5373	Remote Similarity	NPC51032
0.5362	Remote Similarity	NPC106976
0.5294	Remote Similarity	NPC149026
0.5294	Remote Similarity	NPC265040
0.5294	Remote Similarity	NPC102540
0.5294	Remote Similarity	NPC250214
0.5286	Remote Similarity	NPC608140
0.5263	Remote Similarity	NPC83357
0.5238	Remote Similarity	NPC194432
0.5224	Remote Similarity	NPC164980
0.5224	Remote Similarity	NPC169591
0.5224	Remote Similarity	NPC298223
0.5224	Remote Similarity	NPC604412
0.5217	Remote Similarity	NPC68104
0.5211	Remote Similarity	NPC36217
0.52	Remote Similarity	NPC224851
0.5195	Remote Similarity	NPC312273
0.5147	Remote Similarity	NPC324436
0.5147	Remote Similarity	NPC78
0.5147	Remote Similarity	NPC150408
0.5147	Remote Similarity	NPC306829
0.5147	Remote Similarity	NPC476342
0.5079	Remote Similarity	NPC1612
0.5079	Remote Similarity	NPC183959
0.5077	Remote Similarity	NPC474208
0.5072	Remote Similarity	NPC221432
0.5072	Remote Similarity	NPC257097
0.5065	Remote Similarity	NPC192686
0.5065	Remote Similarity	NPC278778

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC23871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3351
0.1-0.2	5641
0.2-0.3	149
0.3-0.4	4
0.4-0.5	4
0.5-0.6	1
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
0.5397	Remote Similarity	NPD2393	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