NPASS Compound

Natural Product: NPC229863

Natural Product ID	NPC229863
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	COHHGQPQHHUMDG-QAJALCMSSA-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:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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 88 92 0 0 0 0 0 0 0 0999 V2000 7.9544 0.9051 1.9322 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8834 1.0738 0.8446 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6885 0.1325 -0.0185 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7798 -0.0277 -1.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8633 1.0773 -1.4501 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2967 2.2208 -2.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4081 3.2257 -2.3620 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0819 3.0930 -2.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6475 1.9226 -1.3959 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3266 1.7620 -1.0562 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5004 2.6705 -1.3133 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9654 0.5597 -0.4233 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8703 -0.4221 -0.1426 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5369 -1.6652 0.5108 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4941 -2.6882 0.4251 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3368 -3.9057 1.0440 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2097 -4.1656 1.7844 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2495 -3.1879 1.8926 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4334 -1.9498 1.2504 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9857 -5.3659 2.4321 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9444 -6.4026 2.3504 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1453 -0.1980 -0.5054 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5132 0.9030 -1.0949 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4060 0.4445 -0.1064 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3192 -0.0400 -1.0663 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4388 0.9523 -1.3768 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0006 0.4932 -2.7190 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5627 -0.8936 -2.4881 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5600 -1.8001 -1.8112 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3124 -3.0155 -1.3142 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9394 -1.2155 -0.7387 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9394 -1.5024 -3.6770 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0664 1.2959 -3.1212 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5007 0.7749 -0.4617 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8385 1.9728 0.1522 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2514 2.4024 -0.0509 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2526 1.6641 0.7754 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7994 1.4496 2.1947 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3459 1.1130 2.2562 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1779 -0.3612 2.0062 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8861 -0.7853 2.2626 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5412 1.9150 1.4966 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1332 2.5448 2.9967 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6106 0.4807 0.1503 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3235 3.7615 0.3331 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1541 4.0758 -2.3025 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6300 2.3905 -2.4224 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1622 2.3544 0.9116 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4754 1.1743 2.8825 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7845 1.6113 1.7492 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2623 -0.1540 1.9737 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3733 -0.7657 0.1368 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3495 -0.2670 -2.1025 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1914 -0.9941 -0.9981 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7791 4.1135 -2.8521 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -2.5164 -0.1564 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0830 -4.6970 0.9738 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6561 -3.3379 2.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3164 -1.1861 1.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7144 -7.2088 3.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9320 -5.9469 2.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9061 -6.8298 1.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7568 -0.1937 -2.0234 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1003 1.9824 -1.4108 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2029 0.4808 -3.4974 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4254 -0.7830 -1.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8201 -2.1737 -2.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0800 -3.3109 -2.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8716 -2.6932 -0.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6329 -3.8480 -1.0618 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9186 -1.6449 -3.6788 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8781 1.6969 -4.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1620 2.7614 -0.2731 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5811 2.3771 -1.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1796 2.2921 0.8373 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3629 0.5860 2.6068 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0259 1.2803 3.3270 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5568 -0.6813 1.0250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8243 -0.8767 2.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9246 -1.7355 2.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0250 2.4604 3.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5107 0.5219 -0.2437 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5639 4.0234 0.8950 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9345 4.3506 -3.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3773 1.8536 -2.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2757 2.8114 1.9442 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0710 2.2761 0.7840 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6101 3.1517 0.2523 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 2 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 17 20 1 0 20 21 1 0 13 22 1 0 22 23 1 0 12 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 28 32 1 0 27 33 1 0 26 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 8 46 1 0 6 47 1 0 2 48 1 0 23 5 1 0 31 25 1 0 42 35 1 0 23 9 2 0 19 14 1 0 1 49 1 0 1 50 1 0 1 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 7 55 1 0 15 56 1 0 16 57 1 0 18 58 1 0 19 59 1 0 21 60 1 0 21 61 1 0 21 62 1 0 25 63 1 6 26 64 1 6 27 65 1 6 28 66 1 1 29 67 1 6 30 68 1 0 30 69 1 0 30 70 1 0 32 71 1 0 33 72 1 0 35 73 1 6 36 74 1 6 37 75 1 1 38 76 1 1 39 77 1 1 40 78 1 0 40 79 1 0 41 80 1 0 43 81 1 0 44 82 1 0 45 83 1 0 46 84 1 0 47 85 1 0 48 86 1 0 48 87 1 0 48 88 1 0 M END

Standard InCHIKey	COHHGQPQHHUMDG-QAJALCMSSA-N
Standard InCHI	InChI=1S/C33H40O15/c1-13(2)5-10-17-18(35)11-19(36)21-24(39)30(28(46-29(17)21)15-6-8-16(43-4)9-7-15)47-33-31(26(41)22(37)14(3)44-33)48-32-27(42)25(40)23(38)20(12-34)45-32/h5-9,11,14,20,22-23,25-27,31-38,40-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25-,26+,27+,31+,32-,33+/m0/s1
SMILES	CC(=CCc1c(cc(c2c(=O)c(c(c3ccc(cc3)OC)oc12)O[C@@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	676.24	Volume:	644.667 ? Van der Waals volume.
Dense:	1.049	LogP:	2.16 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.525 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.177 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.143	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.922	Fsp³:	0.485
MCE-18:	122.694 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.692	Fluc inhibitor:	0.291 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.889 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.748 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.078	Promiscuous compounds:	0.159

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.192	MDCK Permeability:	-5.284
Pgp-inhibitor:	0.0	Pgp-substrate:	0.874
PAMPA:	0.999 ? 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):	0.045
20% Bioavailability (F20%):	0.016	30% Bioavailability (F30%):	0.692
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.027
Plasma Protein Binding (PPB):	85.891%	Volume Distribution (VD):	-0.053
Fu:	15.844% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.203
BSEP inhibitor:	0.849

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.618
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.132
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

1.598

Half-life (T1/2):

4.03

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.167
Human Hepatotoxicity (H-HT):	0.511	Drug-induced Liver Injury (DILI):	0.932
AMES Toxicity:	0.887	Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.026	Skin Sensitization:	0.999
Carcinogencity:	0.05	Eye Corrosion:	0.0
Eye Irritation:	0.051	Respiratory Toxicity:	0.206
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.965
Hematotoxicity:	0.285	Drug-induced Nephrotoxicity:	0.739
Genotoxicity:	0.803	RPMI-8226 Immunitoxicity:	0.132
A549 Cytotoxicity:	0.258	Hek293 Cytotoxicity:	0.291
BCF:	0.886 ? 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:	3.703 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.499 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.661 ? 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
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2007.07.001]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	root	n.a.	n.a.	PMID[15921428]
NPO8129	Inocybe geophylla	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10010	Evernia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11339	Litsea salicifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8609	Hopea utilis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5534	Alternaria kikuchiana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7874	Helichrysum lepidissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1695	Monascus pilosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12828	Dysidea tupha	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10010	Evernia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12602	Leuzea centauroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO218	Acer carpinifolium	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11506	Stipa vaseyi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26095	Hypericum revolutum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5534	Alternaria kikuchiana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1695	Monascus pilosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12118	Cleistopholis staudtii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11339	Litsea salicifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6861	Galium dasypodum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO940	Vernonia anisochaetoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12828	Dysidea tupha	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4759	Helleborus multifidus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10970	Osmorhiza aristata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8129	Inocybe geophylla	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7874	Helichrysum lepidissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4322	Scabiosa succisa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8609	Hopea utilis	Species	Dipterocarpaceae	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 NPC229863 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	12611
0.1-0.2	31385
0.2-0.3	5028
0.3-0.4	596
0.4-0.5	197
0.5-0.6	34
0.6-0.7	2
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
0.7528	Intermediate Similarity	NPC278419
0.7528	Intermediate Similarity	NPC179198
0.64	Remote Similarity	NPC5319
0.6383	Remote Similarity	NPC66087
0.5825	Remote Similarity	NPC482026
0.58	Remote Similarity	NPC163242
0.58	Remote Similarity	NPC272068
0.5784	Remote Similarity	NPC240306
0.5714	Remote Similarity	NPC170052
0.5714	Remote Similarity	NPC476215
0.5714	Remote Similarity	NPC135846
0.5603	Remote Similarity	NPC480443
0.5588	Remote Similarity	NPC155877
0.5566	Remote Similarity	NPC220173
0.5534	Remote Similarity	NPC470444
0.5524	Remote Similarity	NPC35119
0.55	Remote Similarity	NPC254855
0.55	Remote Similarity	NPC94610
0.55	Remote Similarity	NPC95866
0.5464	Remote Similarity	NPC472459
0.5463	Remote Similarity	NPC602448
0.5446	Remote Similarity	NPC473682
0.5424	Remote Similarity	NPC480442
0.5421	Remote Similarity	NPC76831
0.5377	Remote Similarity	NPC32641
0.5377	Remote Similarity	NPC256188
0.5238	Remote Similarity	NPC131745
0.5192	Remote Similarity	NPC470405
0.5149	Remote Similarity	NPC136761
0.5133	Remote Similarity	NPC48984
0.5102	Remote Similarity	NPC64305
0.5088	Remote Similarity	NPC25523
0.5055	Remote Similarity	NPC273538
0.5046	Remote Similarity	NPC142142
0.5043	Remote Similarity	NPC488734
0.5043	Remote Similarity	NPC488735
0.5043	Remote Similarity	NPC488732
0.5043	Remote Similarity	NPC488738

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC229863 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3913
0.1-0.2	5120
0.2-0.3	109
0.3-0.4	6
0.4-0.5	0
0.5-0.6	1
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
0.64	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5055	Remote Similarity	NPD4378	Phase 3

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