NPASS Compound

Natural Product: NPC87571

Natural Product ID	NPC87571
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LGJMUZUPVCAVPU-KZXGMYDKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15559396
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 82 85 0 0 0 0 0 0 0 0999 V2000 7.1013 -2.3799 -0.7990 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0876 -0.8885 -0.6141 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8956 -0.4438 0.2207 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6209 -0.8559 -0.4769 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3973 -0.4591 0.2761 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0936 -0.8423 -0.3657 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9997 -2.3375 -0.5124 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9911 -0.2786 0.5026 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2247 1.2368 0.5240 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1144 1.9006 0.4694 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0621 0.7717 0.6554 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4318 0.9807 0.1383 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0612 2.1041 0.9747 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4394 1.7570 1.4534 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2803 1.0832 0.4219 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5904 0.6861 1.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5372 0.0645 0.0589 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8287 -1.1243 -0.5418 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4325 -1.3081 -0.0509 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5978 -0.0690 -0.2737 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4015 0.1749 -1.7351 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2398 -0.2475 0.3806 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5944 -1.5241 0.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1214 -1.5923 0.0958 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3717 -0.3363 -0.1403 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2283 0.0337 -1.5873 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8249 1.0449 -0.8973 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9683 1.0227 0.5394 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9762 1.8917 -0.6780 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2709 1.3434 1.2911 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3504 -2.6562 -1.5746 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9664 -2.9381 0.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1124 -2.6362 -1.2301 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0055 -0.4302 -1.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0386 -0.5788 -0.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9470 -1.0046 1.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6784 -1.9507 -0.6231 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6113 -0.4271 -1.5261 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4573 0.6484 0.4480 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4823 -0.8950 1.3133 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0805 -0.3682 -1.3727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6149 -2.6555 -1.5156 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3549 -2.7738 0.3030 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9618 -2.8673 -0.3980 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0538 -0.7052 1.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7418 1.4912 1.4900 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8199 1.5583 -0.3419 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3179 2.4183 -0.4932 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2430 2.6100 1.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0993 0.4308 1.7082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4524 1.3411 -0.9002 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1013 3.0571 0.4067 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4483 2.3239 1.8805 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4405 1.2264 2.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9450 2.7422 1.6816 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5315 1.8264 -0.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0755 1.6421 1.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4651 0.0732 1.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4643 -0.1841 0.5763 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4264 -2.0272 -0.2187 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9363 -1.0847 -1.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0152 -2.2094 -0.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4929 -1.5080 1.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2289 1.2758 -1.8959 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5165 -0.3205 -2.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2708 -0.1623 -2.3619 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4506 -0.2779 1.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9320 -1.8819 -1.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0073 -2.3294 0.6839 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7687 -2.3400 -0.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7795 -2.0189 1.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1864 -0.8360 -2.1213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1937 0.2620 -2.0825 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4810 0.8575 -1.6945 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7617 0.6254 -1.8029 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1620 1.3593 1.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7849 1.5855 -1.3745 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2715 2.9235 -0.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0031 2.0021 -1.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5239 0.5470 2.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1161 2.2820 1.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0893 1.5486 0.5639 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 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 1 0 20 21 1 6 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 17 27 1 0 3 28 1 0 28 29 1 0 28 30 1 0 25 8 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 1 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 6 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 1 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 1 12 51 1 6 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 1 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 21 64 1 0 21 65 1 0 21 66 1 0 22 67 1 1 23 68 1 0 23 69 1 0 24 70 1 0 24 71 1 0 26 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 28 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 30 81 1 0 30 82 1 0 M END

Standard InCHIKey	LGJMUZUPVCAVPU-KZXGMYDKSA-N
Standard InCHI	InChI=1S/C29H52O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h19-27,30H,7-18H2,1-6H3/t20-,21-,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.4	Volume:	484.704 ? Van der Waals volume.
Dense:	0.859	LogP:	8.459 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.539 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.131 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	20.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.463	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.371	Fsp³:	1.0
MCE-18:	69.828 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.753	Fluc inhibitor:	0.012 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.761	Promiscuous compounds:	0.025

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.141	MDCK Permeability:	-4.997
Pgp-inhibitor:	0.001	Pgp-substrate:	0.04
PAMPA:	0.06 ? 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%):	0.006	30% Bioavailability (F30%):	0.087
50% Bioavailability (F50%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	0.018
Plasma Protein Binding (PPB):	94.025%	Volume Distribution (VD):	-0.117
Fu:	8.859% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.194
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.13
CYP2C19-inhibitor:	0.992	CYP2C19-substrate:	0.96
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.131	CYP2D6-substrate:	0.49
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.988 ? 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):

14.896

Half-life (T1/2):

0.804

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.45
Human Hepatotoxicity (H-HT):	0.751	Drug-induced Liver Injury (DILI):	0.126
AMES Toxicity:	0.073	Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.551	Skin Sensitization:	0.997
Carcinogencity:	0.834	Eye Corrosion:	0.969
Eye Irritation:	0.996	Respiratory Toxicity:	0.942
Drug-induced Neurotoxicity:	0.069	Ototoxicity:	0.454
Hematotoxicity:	0.184	Drug-induced Nephrotoxicity:	0.648
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.625	Hek293 Cytotoxicity:	0.556
BCF:	3.259 ? 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:	4.929 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.141 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.6 ? 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
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542343]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	roots	n.a.	n.a.	PMID[14664512]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25172742]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38358042]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677276]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26371	Sorghum bicolor	Species	Poaceae	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 NPC87571 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	27021
0.1-0.2	20731
0.2-0.3	1762
0.3-0.4	245
0.4-0.5	70
0.5-0.6	19
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC148174
0.7556	Intermediate Similarity	NPC71460
0.7556	Intermediate Similarity	NPC218585
0.6667	Remote Similarity	NPC114891
0.6346	Remote Similarity	NPC167702
0.6346	Remote Similarity	NPC280026
0.625	Remote Similarity	NPC320549
0.625	Remote Similarity	NPC156277
0.625	Remote Similarity	NPC58057
0.625	Remote Similarity	NPC151018
0.62	Remote Similarity	NPC254340
0.5965	Remote Similarity	NPC323180
0.5833	Remote Similarity	NPC281540
0.5833	Remote Similarity	NPC159654
0.5833	Remote Similarity	NPC167995
0.5833	Remote Similarity	NPC118937
0.5741	Remote Similarity	NPC10476
0.5741	Remote Similarity	NPC192456
0.5667	Remote Similarity	NPC320478
0.5636	Remote Similarity	NPC257347
0.5385	Remote Similarity	NPC327728
0.5385	Remote Similarity	NPC6120
0.5385	Remote Similarity	NPC131892
0.5385	Remote Similarity	NPC213178
0.5385	Remote Similarity	NPC103822
0.5357	Remote Similarity	NPC230301
0.5263	Remote Similarity	NPC477817
0.5179	Remote Similarity	NPC247325
0.5088	Remote Similarity	NPC470360
0.5088	Remote Similarity	NPC603222

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7857
0.1-0.2	1173
0.2-0.3	82
0.3-0.4	23
0.4-0.5	7
0.5-0.6	4
0.6-0.7	3
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
0.6346	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4808	Phase 2
0.625	Remote Similarity	NPD4809	Phase 4
0.5385	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5385	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5357	Remote Similarity	NPD7339	Approved
0.5283	Remote Similarity	NPD4787	Phase 1

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