NPASS Compound

Natural Product: NPC76020

Natural Product ID	NPC76020
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MRPDHXXPDCVBPQ-BBGWOQPJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101165165
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

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 61 62 0 0 0 0 0 0 0 0999 V2000 -4.4544 1.6016 0.8983 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1355 1.0652 0.3134 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3397 0.9571 -1.1503 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1019 -0.3499 -1.4077 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0941 -1.4218 -1.1070 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6609 -1.4277 0.3193 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.4645 1.0305 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2643 -2.0781 0.3312 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6483 -0.1333 1.0272 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2778 0.1043 1.5637 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3628 0.7508 0.8263 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9993 0.9775 1.3814 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0581 2.4185 1.8826 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9147 0.7595 0.3648 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8292 -0.2408 0.6652 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7729 -1.4091 -0.2681 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2637 -1.1271 -1.6467 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9304 0.2283 -1.6517 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8213 0.2728 -0.4104 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6622 1.5444 -0.5329 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4217 1.5263 -1.6859 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0805 0.3181 0.7391 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6644 0.4516 -2.8025 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2438 -1.2346 -2.5755 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5798 -2.4202 0.2956 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4664 -0.2723 2.1786 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2199 -0.4324 -0.5909 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0525 2.1132 0.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2610 2.3442 1.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0170 0.7708 1.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4163 1.9236 0.4775 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4403 0.9385 -1.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0290 1.7748 -1.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3721 -0.3812 -2.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2454 -1.2782 -1.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5713 -2.4010 -1.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9894 -3.1716 0.3171 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9665 -3.0369 1.7674 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3755 -1.9655 1.5685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3921 -3.1542 0.1764 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.9285 1.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6257 -1.6265 -0.4502 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0193 -0.2569 2.5717 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6798 1.0769 -0.1561 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1362 0.3375 2.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7640 2.5138 2.7424 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0603 2.7311 2.2698 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3065 3.1282 1.0651 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5986 -0.6460 1.6942 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7627 -1.8282 -0.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0550 -1.8680 -1.9543 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1402 0.9955 -1.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5121 -0.5873 -0.4712 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3414 1.5820 0.3456 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9760 2.4243 -0.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2369 0.9797 -1.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1572 0.9048 -3.5184 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6682 -2.0049 -2.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1574 -3.3050 0.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2575 0.5076 2.7383 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9861 0.0012 -1.0313 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 6 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 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 19 22 1 0 18 23 1 0 17 24 1 0 16 25 1 0 9 26 1 1 4 27 1 0 9 2 1 0 22 15 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 6 3 32 1 0 3 33 1 0 4 34 1 6 5 35 1 0 5 36 1 0 7 37 1 0 7 38 1 0 7 39 1 0 8 40 1 0 8 41 1 0 8 42 1 0 10 43 1 0 11 44 1 0 12 45 1 1 13 46 1 0 13 47 1 0 13 48 1 0 15 49 1 1 16 50 1 6 17 51 1 6 18 52 1 1 19 53 1 1 20 54 1 0 20 55 1 0 21 56 1 0 23 57 1 0 24 58 1 0 25 59 1 0 26 60 1 0 27 61 1 0 M END

Standard InCHIKey	MRPDHXXPDCVBPQ-BBGWOQPJSA-N
Standard InCHI	InChI=1S/C19H34O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h5-6,10-17,20-25H,7-9H2,1-4H3/b6-5+/t10-,11+,12+,13-,14-,15+,16-,17-,19-/m1/s1
SMILES	C[C@@H]1C[C@@H](CC(C)(C)[C@]1(/C=C/[C@H](C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	390.23	Volume:	387.753 ? Van der Waals volume.
Dense:	1.006	LogP:	-0.013 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.442 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.069 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	13.0
TPSA:	139.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	6.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.339	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.893	Fsp³:	0.895
MCE-18:	52.222 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.493	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.375	Promiscuous compounds:	0.286

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.681	MDCK Permeability:	-5.265
Pgp-inhibitor:	0.0	Pgp-substrate:	0.542
PAMPA:	0.996 ? 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):	0.033
20% Bioavailability (F20%):	0.373	30% Bioavailability (F30%):	0.838
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.042
Plasma Protein Binding (PPB):	43.679%	Volume Distribution (VD):	-0.492
Fu:	57.439% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.108
BSEP inhibitor:	0.046

ADMET: Metabolism

CYP1A2-inhibitor:	0.012	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.174	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.163	CYP3A4-substrate:	0.156
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.568
HLM stability:	0.712 ? 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):

2.814

Half-life (T1/2):

2.693

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.08
Human Hepatotoxicity (H-HT):	0.479	Drug-induced Liver Injury (DILI):	0.364
AMES Toxicity:	0.908	Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.138	Skin Sensitization:	0.999
Carcinogencity:	0.306	Eye Corrosion:	0.001
Eye Irritation:	0.176	Respiratory Toxicity:	0.096
Drug-induced Neurotoxicity:	0.059	Ototoxicity:	0.938
Hematotoxicity:	0.451	Drug-induced Nephrotoxicity:	0.818
Genotoxicity:	0.193	RPMI-8226 Immunitoxicity:	0.137
A549 Cytotoxicity:	0.72	Hek293 Cytotoxicity:	0.367
BCF:	0.256 ? 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:	2.527 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.168 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.185 ? 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
NPO9553	Phyllodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921433]
NPO12367	Diospyros elliptifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9361	Aplophyllum villosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12591	Archaster typicus	Species	Archasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13555	Beaucarnea recurvata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4746	Centaurea arenaria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12819	Clitocybe subilludens	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9989	Cotylelobium scabriusculum	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1326	Cratystylis conocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13042	Diospyros abyssinica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12233	Diospyros peregrina	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6386	Gutenbergia cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8601	Petrosia volcano	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22899	Phaeotremella fagi	Species	Phaeotremellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9553	Phyllodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11333	Trapa japonica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7870	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9246	Breynia officinalis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9246	Breynia officinalis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9246	Breynia officinalis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9553	Phyllodium pulchellum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9361	Aplophyllum villosum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1326	Cratystylis conocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22899	Phaeotremella fagi	Species	Phaeotremellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9783	Mikania scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5131	Scorzonera hispanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12367	Diospyros elliptifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13555	Beaucarnea recurvata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7870	Zanthoxylum piperitum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5831	Mussaenda arcuata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12819	Clitocybe subilludens	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9989	Cotylelobium scabriusculum	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12591	Archaster typicus	Species	Archasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6386	Gutenbergia cordifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8601	Petrosia volcano	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1506	Oldenlandia umbellata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19984	Turpinia ternata	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13042	Diospyros abyssinica	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2627	Verbascum densiflorum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12233	Diospyros peregrina	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11333	Trapa japonica	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9246	Breynia officinalis	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4746	Centaurea arenaria	Species	Asteraceae	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 NPC76020 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	20886
0.1-0.2	24860
0.2-0.3	3469
0.3-0.4	597
0.4-0.5	35
0.5-0.6	8
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC606634
0.6207	Remote Similarity	NPC154127
0.5593	Remote Similarity	NPC169468
0.5593	Remote Similarity	NPC81483
0.5593	Remote Similarity	NPC214277
0.5593	Remote Similarity	NPC307517
0.5593	Remote Similarity	NPC61630
0.5439	Remote Similarity	NPC312325
0.5085	Remote Similarity	NPC25701
0.5085	Remote Similarity	NPC2003

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC76020 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7089
0.1-0.2	1963
0.2-0.3	75
0.3-0.4	23
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
		NPD

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