NPASS Compound

Natural Product: NPC124752

Natural Product ID	NPC124752
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RKHQLCNACMCZQU-GWPISODLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	23265189
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl glycosides

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 73 77 0 0 0 0 0 0 0 0999 V2000 8.9344 -1.0003 -1.2751 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8106 -2.2865 -0.7172 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6017 -2.7793 -0.2298 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4377 -2.0099 -0.2716 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2320 -2.4731 0.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2072 -3.7478 0.7318 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3540 -4.5076 0.7739 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5669 -4.0418 0.2969 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7325 -4.7898 0.3294 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0682 -1.6279 0.1365 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0076 -0.4018 -0.3380 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7297 0.3521 -0.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 -0.1810 0.1102 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6119 1.6161 -0.8150 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5918 2.4991 -0.9280 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3910 2.1310 -1.7726 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2289 3.3973 -2.2894 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4315 3.7559 -1.3975 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3294 2.5488 -1.5432 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6176 1.3735 -0.9067 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3771 1.1124 -1.3587 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8152 1.2834 0.5015 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0948 0.9723 0.9679 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9458 2.0325 1.3401 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5210 3.2166 1.2636 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2001 1.7220 1.7741 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0436 2.7519 2.1382 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3167 2.4614 2.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7054 1.1392 2.6394 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8522 0.1228 2.2727 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5646 0.4002 1.8271 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7335 -0.5276 1.4739 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4834 -0.3228 1.0361 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7076 -1.4964 0.6904 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3708 -1.5409 0.5391 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7502 -2.7289 0.1369 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4412 -3.8924 -0.1206 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8051 -3.8361 0.0389 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4344 -2.6830 0.4314 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8123 -5.0635 -0.5192 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9989 0.8538 3.0873 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5617 4.0484 2.0428 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3781 2.3291 -2.9586 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9016 3.9253 -0.1391 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6001 3.3241 -3.6321 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9335 -0.2498 -0.4408 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9245 -0.9215 -1.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1160 -0.7876 -2.0026 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5708 -1.0312 -0.7055 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2660 -4.1240 1.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3491 -5.5123 1.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1333 -5.2115 -0.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1130 -2.0279 0.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8878 0.0444 -0.7205 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1873 2.8866 0.0580 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0018 3.4444 -1.3951 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8742 1.7023 -2.7767 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5009 4.2303 -2.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9382 4.6602 -1.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3495 2.7083 -1.2678 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2938 0.5015 -1.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9589 3.2888 2.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1498 -0.9251 2.3172 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7935 -0.6696 0.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3328 -2.7070 0.0291 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3636 -4.7605 -0.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5244 -2.6896 0.5444 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2296 -5.6985 -1.2154 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7270 1.5040 2.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9440 4.3530 2.8120 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0417 1.6231 -3.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6626 4.8815 -0.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1637 4.0571 -4.0997 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 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 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 29 41 1 0 27 42 1 0 19 43 1 0 18 44 1 0 17 45 1 0 8 3 1 0 21 16 1 0 33 23 2 0 39 34 1 0 31 26 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 6 50 1 0 7 51 1 0 9 52 1 0 10 53 1 0 11 54 1 0 15 55 1 0 15 56 1 0 16 57 1 6 17 58 1 6 18 59 1 6 19 60 1 1 20 61 1 6 28 62 1 0 30 63 1 0 35 64 1 0 36 65 1 0 38 66 1 0 39 67 1 0 40 68 1 0 41 69 1 0 42 70 1 0 43 71 1 0 44 72 1 0 45 73 1 0 M END

Standard InCHIKey	RKHQLCNACMCZQU-GWPISODLSA-N
Standard InCHI	InChI=1S/C31H28O14/c1-41-20-10-14(2-8-18(20)34)3-9-23(36)42-13-22-25(37)27(39)28(40)31(44-22)45-30-26(38)24-19(35)11-17(33)12-21(24)43-29(30)15-4-6-16(32)7-5-15/h2-12,22,25,27-28,31-35,37,39-40H,13H2,1H3/b9-3+/t22-,25-,27+,28-,31+/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.15	Volume:	590.739 ? Van der Waals volume.
Dense:	1.057	LogP:	1.809 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.781 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.346 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	32.0
TPSA:	225.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.215	Fsp³:	0.226
MCE-18:	107.684 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.735	Fluc inhibitor:	0.846 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.941 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.972 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.055	Promiscuous compounds:	0.543

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.291	MDCK Permeability:	-5.291
Pgp-inhibitor:	0.004	Pgp-substrate:	0.225
PAMPA:	0.959 ? 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):	0.003
20% Bioavailability (F20%):	0.343	30% Bioavailability (F30%):	0.975
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.005
Plasma Protein Binding (PPB):	90.299%	Volume Distribution (VD):	-0.155
Fu:	8.809% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.976
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.014	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.029	CYP2D6-substrate:	0.437
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.992
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.92 ? 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):

2.182

Half-life (T1/2):

3.205

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.404
Human Hepatotoxicity (H-HT):	0.44	Drug-induced Liver Injury (DILI):	0.922
AMES Toxicity:	0.756	Rat Oral Acute Toxicity:	0.123
Maximum Recommended Daily Dose:	0.661	Skin Sensitization:	0.994
Carcinogencity:	0.19	Eye Corrosion:	0.0
Eye Irritation:	0.862	Respiratory Toxicity:	0.101
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.358
Hematotoxicity:	0.019	Drug-induced Nephrotoxicity:	0.168
Genotoxicity:	0.957	RPMI-8226 Immunitoxicity:	0.166
A549 Cytotoxicity:	0.732	Hek293 Cytotoxicity:	0.887
BCF:	0.907 ? 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:	3.732 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.672 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.285 ? 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
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1776	Attalea excelsa	Species	Arecaceae	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 NPC124752 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	16835
0.1-0.2	28077
0.2-0.3	3722
0.3-0.4	737
0.4-0.5	240
0.5-0.6	115
0.6-0.7	61
0.7-0.8	0
0.8-0.85	4
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC85751
0.8889	High Similarity	NPC19240
0.8632	High Similarity	NPC217520
0.8617	High Similarity	NPC470416
0.8602	High Similarity	NPC214621
0.8602	High Similarity	NPC34267
0.8298	Intermediate Similarity	NPC223426
0.8265	Intermediate Similarity	NPC139571
0.8144	Intermediate Similarity	NPC477895
0.8021	Intermediate Similarity	NPC81042
0.7921	Intermediate Similarity	NPC474093
0.7921	Intermediate Similarity	NPC104910
0.7905	Intermediate Similarity	NPC25946
0.7812	Intermediate Similarity	NPC36138
0.7339	Intermediate Similarity	NPC21359
0.7339	Intermediate Similarity	NPC460984
0.7292	Intermediate Similarity	NPC470125
0.7292	Intermediate Similarity	NPC153755
0.7129	Intermediate Similarity	NPC96605
0.7129	Intermediate Similarity	NPC280642
0.7087	Intermediate Similarity	NPC480796
0.7037	Intermediate Similarity	NPC488078
0.703	Intermediate Similarity	NPC218161
0.701	Intermediate Similarity	NPC129264
0.6923	Remote Similarity	NPC472993
0.6903	Remote Similarity	NPC473554
0.6881	Remote Similarity	NPC488079
0.6852	Remote Similarity	NPC470713
0.6842	Remote Similarity	NPC116864
0.6842	Remote Similarity	NPC244776
0.6832	Remote Similarity	NPC477629
0.6723	Remote Similarity	NPC475179
0.6701	Remote Similarity	NPC471079
0.6701	Remote Similarity	NPC609888
0.6634	Remote Similarity	NPC270448
0.6634	Remote Similarity	NPC104883
0.6634	Remote Similarity	NPC488679
0.6633	Remote Similarity	NPC173582
0.6633	Remote Similarity	NPC265885
0.6633	Remote Similarity	NPC181465
0.6633	Remote Similarity	NPC215710
0.6633	Remote Similarity	NPC473438
0.6633	Remote Similarity	NPC253788
0.6505	Remote Similarity	NPC476472
0.6505	Remote Similarity	NPC294815
0.6505	Remote Similarity	NPC16194
0.6429	Remote Similarity	NPC470720
0.6311	Remote Similarity	NPC487501
0.6311	Remote Similarity	NPC473327
0.6237	Remote Similarity	NPC111929
0.6237	Remote Similarity	NPC320283
0.6237	Remote Similarity	NPC41121
0.6226	Remote Similarity	NPC470450
0.6195	Remote Similarity	NPC474522
0.6195	Remote Similarity	NPC470717
0.619	Remote Similarity	NPC80068
0.617	Remote Similarity	NPC77672
0.617	Remote Similarity	NPC133671
0.617	Remote Similarity	NPC135391
0.617	Remote Similarity	NPC78263
0.617	Remote Similarity	NPC250069
0.6154	Remote Similarity	NPC37668
0.6139	Remote Similarity	NPC67326
0.6122	Remote Similarity	NPC223747
0.6117	Remote Similarity	NPC296018
0.6095	Remote Similarity	NPC205824
0.6095	Remote Similarity	NPC270675
0.6095	Remote Similarity	NPC195685
0.6091	Remote Similarity	NPC470712
0.6087	Remote Similarity	NPC241781
0.6082	Remote Similarity	NPC175107
0.6078	Remote Similarity	NPC203259
0.6078	Remote Similarity	NPC33054
0.6078	Remote Similarity	NPC176740
0.6078	Remote Similarity	NPC471725
0.6078	Remote Similarity	NPC134532
0.6078	Remote Similarity	NPC156869
0.6078	Remote Similarity	NPC602582
0.6061	Remote Similarity	NPC203050
0.6061	Remote Similarity	NPC225434
0.6053	Remote Similarity	NPC156785
0.6019	Remote Similarity	NPC478277
0.6019	Remote Similarity	NPC478276
0.6019	Remote Similarity	NPC478275
0.6019	Remote Similarity	NPC92815
0.5982	Remote Similarity	NPC470718
0.5963	Remote Similarity	NPC121703
0.5963	Remote Similarity	NPC599948
0.5918	Remote Similarity	NPC219904
0.5914	Remote Similarity	NPC54802
0.5914	Remote Similarity	NPC197304
0.5913	Remote Similarity	NPC162394
0.5909	Remote Similarity	NPC189564
0.5888	Remote Similarity	NPC471669
0.5865	Remote Similarity	NPC473571
0.5865	Remote Similarity	NPC110941
0.5859	Remote Similarity	NPC120099
0.5851	Remote Similarity	NPC288084
0.5816	Remote Similarity	NPC472459
0.5816	Remote Similarity	NPC471405
0.5794	Remote Similarity	NPC101399
0.5794	Remote Similarity	NPC221288
0.5794	Remote Similarity	NPC217822
0.5794	Remote Similarity	NPC11847
0.5794	Remote Similarity	NPC198938
0.5794	Remote Similarity	NPC194836
0.5794	Remote Similarity	NPC91493
0.5794	Remote Similarity	NPC605081
0.578	Remote Similarity	NPC472994
0.5758	Remote Similarity	NPC159579
0.5741	Remote Similarity	NPC470447
0.5739	Remote Similarity	NPC295625
0.5727	Remote Similarity	NPC603856
0.5714	Remote Similarity	NPC487500
0.5688	Remote Similarity	NPC470449
0.5673	Remote Similarity	NPC39834
0.567	Remote Similarity	NPC127546
0.567	Remote Similarity	NPC57625
0.567	Remote Similarity	NPC173637
0.567	Remote Similarity	NPC317489
0.567	Remote Similarity	NPC223424
0.567	Remote Similarity	NPC600591
0.566	Remote Similarity	NPC154741
0.5645	Remote Similarity	NPC487502
0.5636	Remote Similarity	NPC483767
0.5636	Remote Similarity	NPC483769
0.5636	Remote Similarity	NPC483768
0.5636	Remote Similarity	NPC483766
0.5612	Remote Similarity	NPC145038
0.5612	Remote Similarity	NPC56077
0.5612	Remote Similarity	NPC281131
0.5612	Remote Similarity	NPC64305
0.5612	Remote Similarity	NPC253662
0.5612	Remote Similarity	NPC265530
0.5612	Remote Similarity	NPC179950
0.5612	Remote Similarity	NPC88789
0.5612	Remote Similarity	NPC491374
0.5603	Remote Similarity	NPC488734
0.5603	Remote Similarity	NPC488735
0.5603	Remote Similarity	NPC488739
0.5603	Remote Similarity	NPC488732
0.5603	Remote Similarity	NPC488738
0.56	Remote Similarity	NPC60735
0.56	Remote Similarity	NPC26230
0.5586	Remote Similarity	NPC470455
0.5586	Remote Similarity	NPC483765
0.5545	Remote Similarity	NPC260504
0.5545	Remote Similarity	NPC89809
0.5545	Remote Similarity	NPC609478
0.5528	Remote Similarity	NPC231787
0.5514	Remote Similarity	NPC488074
0.5508	Remote Similarity	NPC470719
0.55	Remote Similarity	NPC325555
0.55	Remote Similarity	NPC226304
0.5472	Remote Similarity	NPC65563
0.5472	Remote Similarity	NPC470949
0.5463	Remote Similarity	NPC12013
0.5463	Remote Similarity	NPC11432
0.5463	Remote Similarity	NPC477613
0.544	Remote Similarity	NPC72554
0.5439	Remote Similarity	NPC292019
0.5439	Remote Similarity	NPC202908
0.5439	Remote Similarity	NPC173837
0.5429	Remote Similarity	NPC139320
0.5424	Remote Similarity	NPC480445
0.5421	Remote Similarity	NPC186816
0.5417	Remote Similarity	NPC488737
0.5403	Remote Similarity	NPC275977
0.54	Remote Similarity	NPC291296
0.54	Remote Similarity	NPC46420
0.54	Remote Similarity	NPC488080
0.54	Remote Similarity	NPC10205
0.54	Remote Similarity	NPC169977
0.5398	Remote Similarity	NPC89052
0.5398	Remote Similarity	NPC203145
0.5392	Remote Similarity	NPC476869
0.5391	Remote Similarity	NPC164704
0.537	Remote Similarity	NPC488073
0.537	Remote Similarity	NPC126784
0.537	Remote Similarity	NPC241423
0.5361	Remote Similarity	NPC276222
0.5361	Remote Similarity	NPC274618
0.5361	Remote Similarity	NPC118284
0.5361	Remote Similarity	NPC608147
0.5354	Remote Similarity	NPC249560
0.5306	Remote Similarity	NPC67037
0.5306	Remote Similarity	NPC255615
0.5294	Remote Similarity	NPC129217
0.5273	Remote Similarity	NPC476620
0.5271	Remote Similarity	NPC97817
0.5268	Remote Similarity	NPC292929
0.5268	Remote Similarity	NPC221342
0.5268	Remote Similarity	NPC470445
0.5268	Remote Similarity	NPC476470
0.5258	Remote Similarity	NPC291153
0.5253	Remote Similarity	NPC135599
0.5253	Remote Similarity	NPC73855
0.5253	Remote Similarity	NPC113968
0.5253	Remote Similarity	NPC328940
0.5253	Remote Similarity	NPC277174

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC124752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4218
0.1-0.2	4859
0.2-0.3	58
0.3-0.4	11
0.4-0.5	3
0.5-0.6	0
0.6-0.7	1
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
0.6078	Remote Similarity	NPD6797	Phase 2

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