NPASS Compound

Natural Product: NPC580234

Natural Product ID	NPC580234
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3~{S},8~{S},9~{R},10~{R},13~{R},14~{S},17~{R})-17-[(1~{S},2~{S},4~{R})-2-hydroxy-1,4,5-trimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthren-3-ol
IUPAC Name	(3~{S},8~{S},9~{R},10~{R},13~{R},14~{S},17~{R})-17-[(1~{S},2~{S},4~{R})-2-hydroxy-1,4,5-trimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthren-3-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 78 81 0 0 0 0 0 0 0 0999 V2000 -7.8580 -1.9574 0.1841 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7056 -1.1291 -0.2770 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0890 -1.8154 -1.4773 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6744 -0.8598 0.7962 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2070 -0.1312 1.9783 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4980 -0.1735 0.1218 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4003 0.1487 1.0894 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8771 1.0072 2.0783 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2116 0.6658 0.3461 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5730 1.9266 -0.3625 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9922 0.8002 1.2111 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6541 -0.5617 1.8214 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7634 -0.4096 2.2580 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3488 0.7232 1.4588 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7025 0.4112 0.9726 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7170 1.5148 1.1477 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0571 0.9318 0.8840 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1857 0.0402 -0.0490 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5431 -0.5604 -0.3315 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8654 -0.1262 -1.7490 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4147 -1.1448 -2.5144 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7635 0.5991 -2.4348 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3963 -0.0029 -2.3022 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0898 -0.4871 -0.9190 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3259 -2.0092 -0.9480 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7370 -0.2225 -0.4017 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8084 0.5380 -1.3238 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4120 0.2811 -0.7667 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2900 1.1084 0.4832 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3271 2.5914 0.1827 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5600 -2.0383 -0.6976 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5389 -3.0244 0.3617 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4557 -1.5457 0.9995 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1259 -0.1582 -0.6770 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4732 -2.6937 -1.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9079 -2.2645 -2.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4933 -1.1122 -2.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2942 -1.8587 1.1246 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1939 0.9621 1.7897 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2113 -0.5107 2.2226 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5668 -0.4038 2.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0614 -0.9566 -0.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8574 0.6179 -0.5169 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1621 -0.8056 1.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2758 1.7532 2.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0080 -0.0985 -0.4647 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2386 1.9558 -1.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2599 2.8635 0.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6969 2.0898 -0.4557 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1367 1.5105 2.0160 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8026 -1.3828 1.1222 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3240 -0.7081 2.6996 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8633 -0.2620 3.3614 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3366 -1.3334 1.9529 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4533 1.5759 2.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0968 -0.4127 1.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6461 1.8706 2.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6173 2.3420 0.4155 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9009 1.2619 1.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5184 -1.6616 -0.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2866 -0.2328 0.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7047 0.6252 -1.6300 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2298 -1.4964 -2.0906 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7575 1.7010 -2.1840 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0116 0.5892 -3.5374 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 0.7748 -2.6693 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3245 -0.8275 -3.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6401 -2.3304 0.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0923 -2.3068 -1.6588 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3749 -2.5011 -1.2504 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2016 -1.2123 -0.2435 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8025 0.0779 -2.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9599 1.6144 -1.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3657 0.4775 -1.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3892 -0.7931 -0.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3768 2.9618 0.0879 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1276 2.7575 -0.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1350 3.2301 0.9287 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 4 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 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 2 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 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 29 11 1 0 29 14 1 0 26 15 1 0 24 18 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 1 5 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 7 44 1 1 8 45 1 0 9 46 1 6 10 47 1 0 10 48 1 0 10 49 1 0 11 50 1 1 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 1 15 56 1 1 16 57 1 0 16 58 1 0 17 59 1 0 19 60 1 0 19 61 1 0 20 62 1 1 21 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 1 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	LSZJAIFORSLKOY-XONIIBKRSA-N
Standard InCHI	InChI=1S/C28H48O2/c1-17(2)18(3)15-26(30)19(4)23-9-10-24-22-8-7-20-16-21(29)11-13-27(20,5)25(22)12-14-28(23,24)6/h7,17-19,21-26,29-30H,8-16H2,1-6H3/t18-,19+,21+,22+,23-,24+,25-,26+,27+,28+/m1/s1
SMILES	CC(C)[C@H](C)C[C@H](O)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.37	Volume:	473.562 ? Van der Waals volume.
Dense:	0.879	LogP:	5.246 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.263 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.831 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	20.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.495	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.585	Fsp³:	0.929
MCE-18:	71.556 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.937	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.506	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.247	MDCK Permeability:	-5.094
Pgp-inhibitor:	0.054	Pgp-substrate:	0.817
PAMPA:	0.674 ? 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):	0.0
20% Bioavailability (F20%):	0.412	30% Bioavailability (F30%):	0.175
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017	MRP1:	0.567
Plasma Protein Binding (PPB):	69.955%	Volume Distribution (VD):	-0.191
Fu:	30.039% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.787
OATP1B3 inhibitor:	0.099	BCRP inhibitor:	0.134
BSEP inhibitor:	0.436

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.262	CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.536	CYP3A4-substrate:	0.995
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.509
HLM stability:	0.761 ? 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):

13.443

Half-life (T1/2):

0.762

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.132
Human Hepatotoxicity (H-HT):	0.349	Drug-induced Liver Injury (DILI):	0.199
AMES Toxicity:	0.413	Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.5	Skin Sensitization:	0.963
Carcinogencity:	0.881	Eye Corrosion:	0.035
Eye Irritation:	0.57	Respiratory Toxicity:	0.69
Drug-induced Neurotoxicity:	0.044	Ototoxicity:	0.762
Hematotoxicity:	0.532	Drug-induced Nephrotoxicity:	0.928
Genotoxicity:	0.008	RPMI-8226 Immunitoxicity:	0.095
A549 Cytotoxicity:	0.784	Hek293 Cytotoxicity:	0.713
BCF:	2.253 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.025 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.113 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.744 ? 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
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	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 NPC580234 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	24080
0.1-0.2	22243
0.2-0.3	3149
0.3-0.4	251
0.4-0.5	63
0.5-0.6	15
0.6-0.7	33
0.7-0.8	2
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8163	Intermediate Similarity	NPC162742
0.8163	Intermediate Similarity	NPC304309
0.8163	Intermediate Similarity	NPC470228
0.8	Intermediate Similarity	NPC600590
0.7358	Intermediate Similarity	NPC230301
0.7308	Intermediate Similarity	NPC22105
0.7308	Intermediate Similarity	NPC34019
0.7308	Intermediate Similarity	NPC107059
0.717	Intermediate Similarity	NPC136188
0.717	Intermediate Similarity	NPC28657
0.717	Intermediate Similarity	NPC474216
0.717	Intermediate Similarity	NPC154330
0.7037	Intermediate Similarity	NPC113733
0.7037	Intermediate Similarity	NPC198968
0.7037	Intermediate Similarity	NPC285893
0.7037	Intermediate Similarity	NPC134847
0.6909	Remote Similarity	NPC241290
0.6909	Remote Similarity	NPC164840
0.6909	Remote Similarity	NPC484739
0.6909	Remote Similarity	NPC209944
0.6909	Remote Similarity	NPC264245
0.6909	Remote Similarity	NPC155986
0.6842	Remote Similarity	NPC474759
0.6786	Remote Similarity	NPC321381
0.6727	Remote Similarity	NPC609126
0.6667	Remote Similarity	NPC474778
0.6667	Remote Similarity	NPC472265
0.6667	Remote Similarity	NPC221758
0.6667	Remote Similarity	NPC474733
0.6667	Remote Similarity	NPC59453
0.6552	Remote Similarity	NPC603646
0.6441	Remote Similarity	NPC473943
0.6441	Remote Similarity	NPC155011
0.6379	Remote Similarity	NPC33913
0.6333	Remote Similarity	NPC47761
0.6333	Remote Similarity	NPC488870
0.6316	Remote Similarity	NPC51014
0.6271	Remote Similarity	NPC477522
0.625	Remote Similarity	NPC328313
0.6207	Remote Similarity	NPC328714
0.6167	Remote Similarity	NPC243985
0.6167	Remote Similarity	NPC280710
0.6167	Remote Similarity	NPC240650
0.6129	Remote Similarity	NPC474970
0.6102	Remote Similarity	NPC1272
0.6102	Remote Similarity	NPC318495
0.6102	Remote Similarity	NPC470614
0.6066	Remote Similarity	NPC474164
0.6038	Remote Similarity	NPC96319
0.5932	Remote Similarity	NPC470383
0.5902	Remote Similarity	NPC7505
0.5902	Remote Similarity	NPC82986
0.5781	Remote Similarity	NPC601043
0.5781	Remote Similarity	NPC605412
0.5738	Remote Similarity	NPC474732
0.569	Remote Similarity	NPC20688
0.5517	Remote Similarity	NPC151519
0.541	Remote Similarity	NPC87604
0.5345	Remote Similarity	NPC81306
0.5333	Remote Similarity	NPC76879
0.5303	Remote Similarity	NPC176012
0.5152	Remote Similarity	NPC474349
0.5152	Remote Similarity	NPC474189
0.5139	Remote Similarity	NPC3715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC580234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7779
0.1-0.2	1213
0.2-0.3	128
0.3-0.4	23
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	2
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
0.7358	Intermediate Similarity	NPD7339	Approved
0.717	Intermediate Similarity	NPD6942	Phase 4
0.6667	Remote Similarity	NPD4786	Phase 1
0.6038	Remote Similarity	NPD3701	Pre-clinical
0.5517	Remote Similarity	NPD3667	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