NPASS Compound

Natural Product: NPC195685

Natural Product ID	NPC195685
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cosmosiin 6''-(Z)-P-Coumarate
IUPAC Name	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3597473
PubChem CID	16109837
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 68 72 0 0 0 0 0 0 0 0999 V2000 -7.4240 2.2036 -1.2207 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6245 3.5705 -1.0822 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7021 4.0336 -0.3875 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5977 3.1569 0.1810 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3792 1.8156 0.0332 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2663 1.2977 -0.6823 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0892 -0.1163 -0.6811 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0103 -0.8050 -0.5360 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7102 -0.2595 -0.3123 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4375 0.9233 -0.1598 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6004 -1.1660 -0.2585 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3237 -0.5730 -0.0345 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2453 -1.6214 -0.0026 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5686 -2.6009 1.0824 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7606 -2.2876 2.3124 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3010 -2.4232 1.9665 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0256 -1.8174 0.6022 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1288 -1.0447 0.7288 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2674 -1.2258 -0.0282 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4327 -2.1784 -1.0083 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6255 -2.2954 -1.7334 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6946 -1.4588 -1.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8775 -1.5551 -2.1996 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0185 -2.4308 -3.0952 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9016 -0.6542 -1.8813 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6916 0.2801 -0.8949 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7042 1.2577 -0.4978 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9522 1.3326 -1.0725 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8886 2.2887 -0.6540 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5972 3.1895 0.3471 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3488 3.1192 0.9263 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4306 2.1793 0.5137 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5255 4.1436 0.7680 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5482 0.3052 -0.2816 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5334 -0.5032 -0.5179 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3636 -0.3812 0.2002 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7713 -3.2628 -2.7176 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0484 -0.9458 0.2215 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0128 -3.7819 1.9906 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0835 -1.0708 2.8771 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1494 -3.8787 0.6464 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9198 5.3929 -0.2379 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5824 1.9478 -1.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9266 4.2733 -1.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4407 3.5578 0.7232 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0517 1.0909 0.4596 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0401 -0.7189 -0.8300 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1189 -1.9404 -0.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3189 0.0298 0.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1645 0.1615 -0.8508 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2447 -2.1124 -1.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6483 -2.6934 1.2940 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0166 -3.0707 3.0703 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -1.9411 2.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0185 -2.6339 -0.1393 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6348 -2.8550 -1.2326 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8237 -0.7067 -2.4064 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2114 0.6340 -1.8665 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8479 2.3110 -1.1294 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1258 3.8385 1.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4521 2.1301 0.9734 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5193 3.8828 0.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2481 0.3715 0.9671 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5998 -3.0964 -3.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6793 -4.0031 2.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3380 -0.4529 2.9919 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4376 -4.0672 -0.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1881 5.9107 0.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 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 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 30 33 1 0 26 34 1 0 34 35 1 0 35 36 2 0 21 37 1 0 17 38 1 0 16 39 1 0 15 40 1 0 14 41 1 0 3 42 1 0 6 1 1 0 38 13 1 0 36 19 1 0 35 22 1 0 32 27 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 7 47 1 0 8 48 1 0 12 49 1 0 12 50 1 0 13 51 1 6 14 52 1 1 15 53 1 1 16 54 1 1 17 55 1 6 20 56 1 0 25 57 1 0 28 58 1 0 29 59 1 0 31 60 1 0 32 61 1 0 33 62 1 0 36 63 1 0 37 64 1 0 39 65 1 0 40 66 1 0 41 67 1 0 42 68 1 0 M END

Standard InCHIKey	WPQRDUGBKUNFJW-SVZMWWRJSA-N
Standard InCHI	InChI=1S/C30H26O12/c31-17-6-1-15(2-7-17)3-10-25(35)39-14-24-27(36)28(37)29(38)30(42-24)40-19-11-20(33)26-21(34)13-22(41-23(26)12-19)16-4-8-18(32)9-5-16/h1-13,24,27-33,36-38H,14H2/b10-3-/t24-,27-,28+,29-,30-/m1/s1
SMILES	c1cc(ccc1/C=CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](Oc2cc(c3c(=O)cc(c4ccc(cc4)O)oc3c2)O)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.14	Volume:	555.862 ? Van der Waals volume.
Dense:	1.04	LogP:	1.839 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.77 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.471 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	32.0
TPSA:	196.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.138	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.081	Fsp³:	0.2
MCE-18:	101.611 ? 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:	0.765	Fluc inhibitor:	0.985 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.98 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.996 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.15	Promiscuous compounds:	0.513

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.086	MDCK Permeability:	-5.113
Pgp-inhibitor:	0.003	Pgp-substrate:	0.017
PAMPA:	0.99 ? 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):	0.342
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.023
Plasma Protein Binding (PPB):	90.367%	Volume Distribution (VD):	-0.058
Fu:	9.016% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.089
BSEP inhibitor:	0.803

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.168
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.023
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.008	CYP2D6-substrate:	0.992
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.022 ? 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):

2.447

Half-life (T1/2):

3.066

ADMET: Toxicity

hERG Blockers:	0.186	hERG Blockers (10um):	0.656
Human Hepatotoxicity (H-HT):	0.493	Drug-induced Liver Injury (DILI):	0.812
AMES Toxicity:	0.676	Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.465	Skin Sensitization:	0.999
Carcinogencity:	0.016	Eye Corrosion:	0.0
Eye Irritation:	0.883	Respiratory Toxicity:	0.079
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.261
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.239
Genotoxicity:	0.775	RPMI-8226 Immunitoxicity:	0.127
A549 Cytotoxicity:	0.968	Hek293 Cytotoxicity:	0.943
BCF:	0.974 ? 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:	3.949 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.736 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.448 ? 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
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711344]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19025748]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245240]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356064]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22283497]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22351977]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	leaf	Putz City, Chiayi County, Taiwan	2009-Nov	PMID[25999202]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28742368]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29397715]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2012	Turnera diffusa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19826	Helicoverpa armigera	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26103	Streptomyces bobili	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2495	Agave xylonacantha	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6766	Antiphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9567	Enicosanthum cupulare	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10991	Maackia tashiroi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9136	Pseudocyclosorus subochthodes	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8653	Leuconostoc mesenteroides	Species	Leuconostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2012	Turnera diffusa	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3123	Anthemis cretica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19826	Helicoverpa armigera	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26103	Streptomyces bobili	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6766	Antiphiona pinnatisecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9567	Enicosanthum cupulare	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10991	Maackia tashiroi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8764	Laurencia decumbens	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9136	Pseudocyclosorus subochthodes	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26700	Tinospora crispa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28741	Afrocarpus gracilior	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2495	Agave xylonacantha	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	10100.0	nM	PMID[25999202]

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 NPC195685 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	16153
0.1-0.2	28709
0.2-0.3	3704
0.3-0.4	854
0.4-0.5	304
0.5-0.6	80
0.6-0.7	37
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC270675
0.9412	High Similarity	NPC472994
0.8989	High Similarity	NPC472993
0.8315	Intermediate Similarity	NPC80068
0.7912	Intermediate Similarity	NPC477629
0.7604	Intermediate Similarity	NPC473278
0.7473	Intermediate Similarity	NPC64051
0.7423	Intermediate Similarity	NPC480796
0.7143	Intermediate Similarity	NPC44931
0.7011	Intermediate Similarity	NPC27942
0.6804	Remote Similarity	NPC85751
0.6804	Remote Similarity	NPC19240
0.6771	Remote Similarity	NPC210961
0.6771	Remote Similarity	NPC229409
0.6762	Remote Similarity	NPC471030
0.6744	Remote Similarity	NPC331652
0.6735	Remote Similarity	NPC101636
0.6735	Remote Similarity	NPC298171
0.6667	Remote Similarity	NPC39360
0.6667	Remote Similarity	NPC29763
0.6667	Remote Similarity	NPC210003
0.6566	Remote Similarity	NPC36138
0.6562	Remote Similarity	NPC46202
0.65	Remote Similarity	NPC223426
0.6452	Remote Similarity	NPC172807
0.64	Remote Similarity	NPC260504
0.64	Remote Similarity	NPC89809
0.6373	Remote Similarity	NPC599948
0.6354	Remote Similarity	NPC22062
0.6354	Remote Similarity	NPC473634
0.6354	Remote Similarity	NPC210073
0.6354	Remote Similarity	NPC138811
0.6344	Remote Similarity	NPC190003
0.6275	Remote Similarity	NPC214621
0.6275	Remote Similarity	NPC34267
0.6207	Remote Similarity	NPC291153
0.619	Remote Similarity	NPC217520
0.6176	Remote Similarity	NPC484301
0.6162	Remote Similarity	NPC65711
0.6154	Remote Similarity	NPC181712
0.61	Remote Similarity	NPC473623
0.61	Remote Similarity	NPC209296
0.6095	Remote Similarity	NPC477895
0.604	Remote Similarity	NPC488089
0.6038	Remote Similarity	NPC164704
0.6019	Remote Similarity	NPC179862
0.6	Remote Similarity	NPC470416
0.5962	Remote Similarity	NPC81042
0.5962	Remote Similarity	NPC603856
0.5934	Remote Similarity	NPC19709
0.5877	Remote Similarity	NPC199172
0.587	Remote Similarity	NPC95090
0.587	Remote Similarity	NPC27408
0.587	Remote Similarity	NPC189142
0.587	Remote Similarity	NPC77660
0.5789	Remote Similarity	NPC601144
0.5784	Remote Similarity	NPC139060
0.5784	Remote Similarity	NPC476620
0.5773	Remote Similarity	NPC211594
0.5741	Remote Similarity	NPC470715
0.5729	Remote Similarity	NPC311830
0.5714	Remote Similarity	NPC254540
0.5684	Remote Similarity	NPC282169
0.5644	Remote Similarity	NPC186816
0.5638	Remote Similarity	NPC10205
0.5636	Remote Similarity	NPC139571
0.5636	Remote Similarity	NPC470716
0.5625	Remote Similarity	NPC22832
0.5625	Remote Similarity	NPC243930
0.5625	Remote Similarity	NPC298666
0.5607	Remote Similarity	NPC121703
0.5591	Remote Similarity	NPC261866
0.5545	Remote Similarity	NPC473512
0.5545	Remote Similarity	NPC129827
0.5524	Remote Similarity	NPC188815
0.5484	Remote Similarity	NPC473043
0.5463	Remote Similarity	NPC11468
0.5439	Remote Similarity	NPC470717
0.5437	Remote Similarity	NPC470125
0.5435	Remote Similarity	NPC157898
0.5426	Remote Similarity	NPC108831
0.5426	Remote Similarity	NPC182634
0.5421	Remote Similarity	NPC218161
0.5408	Remote Similarity	NPC607707
0.5392	Remote Similarity	NPC65003
0.5391	Remote Similarity	NPC470720
0.5391	Remote Similarity	NPC488079
0.5391	Remote Similarity	NPC488078
0.5385	Remote Similarity	NPC477628
0.537	Remote Similarity	NPC96605
0.537	Remote Similarity	NPC280642
0.5368	Remote Similarity	NPC323593
0.5368	Remote Similarity	NPC203500
0.5361	Remote Similarity	NPC204937
0.5301	Remote Similarity	NPC234133
0.53	Remote Similarity	NPC477848
0.5294	Remote Similarity	NPC35924
0.5294	Remote Similarity	NPC67105
0.5288	Remote Similarity	NPC472992
0.5283	Remote Similarity	NPC294722
0.5263	Remote Similarity	NPC249281
0.5258	Remote Similarity	NPC198324
0.5221	Remote Similarity	NPC488087
0.5208	Remote Similarity	NPC93337
0.5208	Remote Similarity	NPC297987
0.5208	Remote Similarity	NPC146792
0.52	Remote Similarity	NPC276377
0.5192	Remote Similarity	NPC122809
0.5192	Remote Similarity	NPC204693
0.5155	Remote Similarity	NPC46420
0.5155	Remote Similarity	NPC105025
0.5152	Remote Similarity	NPC476869
0.5152	Remote Similarity	NPC476866
0.514	Remote Similarity	NPC479766
0.514	Remote Similarity	NPC486577
0.5138	Remote Similarity	NPC470450
0.513	Remote Similarity	NPC488086
0.5098	Remote Similarity	NPC472876
0.5096	Remote Similarity	NPC479405
0.5096	Remote Similarity	NPC303913
0.5093	Remote Similarity	NPC479765
0.5051	Remote Similarity	NPC20505
0.505	Remote Similarity	NPC476870
0.5048	Remote Similarity	NPC129264
0.5048	Remote Similarity	NPC479404
0.5047	Remote Similarity	NPC483707
0.5047	Remote Similarity	NPC72016

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC195685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4047
0.1-0.2	5006
0.2-0.3	84
0.3-0.4	7
0.4-0.5	5
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
0.61	Remote Similarity	NPD7054	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