NPASS Compound

Natural Product: NPC73723

Natural Product ID	NPC73723
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UVDOOTXXKWLRMZ-LYKPKXNDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21768175
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides and derivatives

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 73 0 0 0 0 0 0 0 0999 V2000 8.0432 -0.0537 -0.4489 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7728 0.6652 -0.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7805 1.9065 0.1018 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5333 0.0535 -0.2171 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3079 0.7464 0.0419 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4612 0.7994 -1.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4651 -0.2815 -1.3439 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6896 -0.6387 -0.1031 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0993 -2.0885 0.2204 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2202 -0.5444 -0.3074 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5603 -1.7788 0.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7983 -1.5194 0.8317 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6284 -0.3691 0.3587 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6273 -0.0643 1.4593 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4355 -0.6900 -0.8784 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8571 0.0866 -2.0191 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0265 1.2003 -1.4099 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8354 0.8450 0.0159 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4186 0.6073 0.4313 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4527 1.8126 0.2631 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6747 1.5677 1.1242 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1301 0.1538 1.1108 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6339 0.1697 1.2460 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6468 -0.5631 2.2308 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2981 1.9278 0.8013 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8769 -0.3644 -0.7190 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8648 -1.3545 -0.7062 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1895 -1.0011 -0.5575 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5588 0.3209 -0.4204 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7617 0.6813 -0.2823 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6258 1.2145 -0.4357 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3452 0.9304 -0.5750 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0804 -1.3770 -1.9420 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3384 0.1643 -1.4979 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0030 -1.1164 -0.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8259 0.4164 0.1875 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6183 1.8117 0.2589 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1754 0.7110 -2.0624 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0091 1.8237 -1.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7083 0.0748 -2.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2195 -2.0965 0.0665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9393 -2.3370 1.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7066 -2.7954 -0.5145 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0483 -0.3468 -1.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8976 -2.3314 -0.8952 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0213 -2.5335 0.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4293 -2.4414 0.7833 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5141 -1.4096 1.8967 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2284 -0.4273 2.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8262 1.0237 1.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5816 -0.6359 1.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -1.7978 -1.0255 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2059 -0.6255 -2.6030 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6024 0.4653 -2.7342 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0959 1.2546 -2.0061 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5173 2.1922 -1.5361 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4349 0.3253 1.5053 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6770 1.9316 -0.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0435 2.7250 0.6619 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4814 2.3153 0.9392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3368 1.7919 2.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0435 -0.8153 1.5475 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8416 0.8401 2.1342 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2750 -0.5075 2.9872 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2384 2.7518 0.2640 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5654 -2.3774 -0.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9767 -1.7540 -0.5445 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6690 1.7473 -0.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6559 -1.0178 -2.6594 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 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 21 22 1 0 22 23 1 0 22 24 1 1 18 25 1 1 15 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 7 33 1 0 23 5 1 0 32 26 2 0 22 8 1 0 19 10 1 0 18 13 1 0 1 34 1 0 1 35 1 0 1 36 1 0 5 37 1 1 6 38 1 0 6 39 1 0 7 40 1 6 9 41 1 0 9 42 1 0 9 43 1 0 10 44 1 6 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 14 49 1 0 14 50 1 0 14 51 1 0 15 52 1 6 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 19 57 1 1 20 58 1 0 20 59 1 0 21 60 1 0 21 61 1 0 23 62 1 0 23 63 1 0 24 64 1 0 25 65 1 0 27 66 1 0 28 67 1 0 32 68 1 0 33 69 1 0 M END

Standard InCHIKey	UVDOOTXXKWLRMZ-LYKPKXNDSA-N
Standard InCHI	InChI=1S/C26H36O7/c1-15(27)33-17-12-21(28)24(3)19-6-9-23(2)18(16-4-5-22(29)32-14-16)8-11-26(23,31)20(19)7-10-25(24,30)13-17/h4-5,14,17-21,28,30-31H,6-13H2,1-3H3/t17-,18+,19-,20+,21+,23+,24-,25-,26-/m0/s1
SMILES	CC(=O)O[C@H]1C[C@H]([C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@@]4([C@@H]3CC[C@@]2(C1)O)O)c1ccc(=O)oc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	460.25	Volume:	466.456 ? Van der Waals volume.
Dense:	0.987	LogP:	1.132 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.648 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.447 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	28.0
TPSA:	117.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.581	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.864	Fsp³:	0.769
MCE-18:	130.87 ? 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:	0.481	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.286 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.062	Promiscuous compounds:	0.705

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.155	MDCK Permeability:	-4.786
Pgp-inhibitor:	0.004	Pgp-substrate:	0.994
PAMPA:	0.996 ? 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):	0.032
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051	MRP1:	0.98
Plasma Protein Binding (PPB):	79.831%	Volume Distribution (VD):	0.13
Fu:	16.914% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.952	BCRP inhibitor:	0.008
BSEP inhibitor:	0.766

ADMET: Metabolism

CYP1A2-inhibitor:	0.016	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.575	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.097	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.146	CYP3A4-substrate:	0.004
CYP2B6-substrate:	0.011	CYP2C8-inhibitor:	0.936
HLM stability:	0.727 ? 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):

7.879

Half-life (T1/2):

2.284

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.111
Human Hepatotoxicity (H-HT):	0.552	Drug-induced Liver Injury (DILI):	0.121
AMES Toxicity:	0.453	Rat Oral Acute Toxicity:	0.731
Maximum Recommended Daily Dose:	0.995	Skin Sensitization:	0.749
Carcinogencity:	0.979	Eye Corrosion:	0.0
Eye Irritation:	0.032	Respiratory Toxicity:	0.734
Drug-induced Neurotoxicity:	0.388	Ototoxicity:	0.208
Hematotoxicity:	0.158	Drug-induced Nephrotoxicity:	0.986
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.396
A549 Cytotoxicity:	0.354	Hek293 Cytotoxicity:	0.919
BCF:	0.526 ? 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:	3.309 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.779 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.143 ? 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
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO9461	Gmelina leichhardtii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8403	Annona coriacea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10101	Rothmannia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12045	Schottera nicaeensis	Species	Phyllophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3670	Crotalaria podocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9015	Solanum arundo	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3313	Crotalaria trichotoma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12045	Schottera nicaeensis	Species	Phyllophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5310	Eucalyptus bakeri	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11673	Koelreuteria paniculata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7322	Plagiochila acanthophylla	Species	Plagiochilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11228	Fritillaria pallidiflora	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4919	Kalanchoe daigremontiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11540	Acacia leptostachya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3313	Crotalaria trichotoma	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13095	Pachycereus tehuantepecanus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10101	Rothmannia macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12761	Rheum hotaoense	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9887	Protohermes grandis	Species	Corydalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9461	Gmelina leichhardtii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4454	Maytenus salicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3670	Crotalaria podocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17461	Hedera canariensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO737	Aspergillus japonicus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO395	Teucrium pilosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9015	Solanum arundo	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8403	Annona coriacea	Species	Annonaceae	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 NPC73723 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	11358
0.1-0.2	36632
0.2-0.3	1760
0.3-0.4	49
0.4-0.5	28
0.5-0.6	25
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9014	High Similarity	NPC55602
0.7143	Intermediate Similarity	NPC488753
0.6538	Remote Similarity	NPC184555
0.6437	Remote Similarity	NPC62172
0.6364	Remote Similarity	NPC137462
0.6292	Remote Similarity	NPC289700
0.5949	Remote Similarity	NPC304276
0.593	Remote Similarity	NPC233041
0.593	Remote Similarity	NPC488752
0.5882	Remote Similarity	NPC154815
0.5882	Remote Similarity	NPC247760
0.5773	Remote Similarity	NPC603497
0.5765	Remote Similarity	NPC44537
0.575	Remote Similarity	NPC171014
0.5732	Remote Similarity	NPC73050
0.5732	Remote Similarity	NPC605625
0.5652	Remote Similarity	NPC145074
0.5652	Remote Similarity	NPC114939
0.5618	Remote Similarity	NPC257610
0.5556	Remote Similarity	NPC47870
0.5432	Remote Similarity	NPC603706
0.5432	Remote Similarity	NPC606351
0.5366	Remote Similarity	NPC481623
0.5306	Remote Similarity	NPC41123
0.5258	Remote Similarity	NPC155529
0.5176	Remote Similarity	NPC12795
0.5158	Remote Similarity	NPC75616
0.5158	Remote Similarity	NPC611669
0.5152	Remote Similarity	NPC16270
0.5114	Remote Similarity	NPC75389
0.5055	Remote Similarity	NPC183603

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC73723 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3116
0.1-0.2	5952
0.2-0.3	81
0.3-0.4	0
0.4-0.5	0
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
0.5158	Remote Similarity	NPD7503	Phase 4

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