NPASS Compound

Natural Product: NPC605954

Natural Product ID	NPC605954
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CUOZRGBQTOSWAY-PWEPJYDOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3987111
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 104109 0 0 0 0 0 0 0 0999 V2000 2.3027 -2.8598 -1.9471 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8431 -1.7135 -1.0578 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0964 -1.2464 -1.8433 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3125 -2.3010 0.1910 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7744 -1.7730 1.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9590 -0.5456 1.4744 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8846 0.5077 2.0130 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6688 1.1775 3.0500 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0463 0.7590 1.3281 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9806 1.7507 1.7660 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0642 2.7092 0.8459 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0917 2.8990 0.0115 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6774 2.8976 -1.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8685 3.1299 -2.1867 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3237 2.0798 0.1725 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3783 2.8068 0.7539 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0988 0.8218 0.9773 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4793 -0.1453 0.2273 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2983 1.1905 2.1786 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9760 2.1743 2.9143 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9254 -0.6403 2.6057 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3845 -1.2348 2.3710 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9339 -1.0738 0.9171 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6506 -2.4301 0.3414 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1026 0.0511 0.4687 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6582 1.2318 0.4025 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0822 1.5169 0.7571 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8269 0.3585 0.2112 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3053 0.5943 0.0240 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0980 0.8078 1.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4162 1.8982 -0.7891 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7667 2.1235 -1.3840 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5889 3.1768 -2.3197 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4349 0.9953 -2.0449 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8393 1.1015 -1.8712 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0674 -0.3712 -1.5410 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0535 -1.2817 -2.7866 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1581 -0.9608 -0.6698 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7537 -0.4792 -0.9077 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5413 -1.7932 -0.2156 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0697 -1.9820 -0.0643 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4104 -0.9117 0.8417 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9836 -1.2114 2.1968 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3500 -0.0587 0.1852 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7848 -0.6837 -1.0603 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6230 -1.0638 -1.7935 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1968 -2.9204 -1.8910 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7530 -3.7835 -1.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6272 -2.7306 -3.0010 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1392 -0.1542 -1.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9344 -1.3660 -2.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0087 -1.7140 -1.4709 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1759 -3.4426 0.2162 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4361 -2.2155 0.2266 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6384 -1.7404 2.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1394 -2.5921 1.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5198 2.2097 2.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4341 3.9795 0.1612 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3231 1.9174 -1.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0089 3.7386 -1.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1510 2.3333 -2.7046 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6917 1.7747 -0.8266 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8947 2.1793 1.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0968 0.4762 1.3245 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6473 -1.0206 0.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1448 0.3489 2.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4638 3.0264 2.9652 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 0.3567 3.1405 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4577 -1.2629 3.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4035 -2.2949 2.6882 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0754 -0.7052 3.0915 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1028 -3.1389 1.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1109 -2.7239 -0.5768 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3883 -2.7486 0.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0919 2.1336 0.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3888 2.5056 0.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1982 1.6344 1.8680 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4618 0.2689 -0.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4639 1.3300 1.9933 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5742 -0.0196 1.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9236 1.5448 1.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6042 1.9356 -1.5158 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3372 2.7174 -0.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4834 2.5812 -0.6393 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5301 4.0518 -1.8371 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3035 1.0874 -3.1515 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9840 1.5156 -0.9612 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0779 -2.3358 -2.5367 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9322 -1.0584 -3.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1584 -1.0574 -3.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9160 -2.0429 -0.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1055 -0.9708 -1.2861 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3872 -0.3918 0.2242 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9866 -0.4734 -1.7469 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8567 -2.6244 -0.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1818 -1.9013 0.6362 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6827 -1.7579 -1.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9127 -2.9918 0.2777 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0216 -0.3643 2.8751 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4016 -2.0777 2.6423 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9917 -1.7234 2.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7461 1.0141 0.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1809 0.0790 -1.8314 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0691 -0.3937 -1.6650 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 5 6 1 0 6 7 1 1 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 6 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 29 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 36 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 1 25 44 1 0 44 45 1 0 45 46 1 0 45 2 1 0 44 6 1 0 19 10 1 0 42 23 1 0 42 28 1 0 39 29 1 0 1 47 1 0 1 48 1 0 1 49 1 0 3 50 1 0 3 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 10 57 1 1 12 58 1 1 13 59 1 0 13 60 1 0 14 61 1 0 15 62 1 6 16 63 1 0 17 64 1 1 18 65 1 0 19 66 1 1 20 67 1 0 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 24 72 1 0 24 73 1 0 24 74 1 0 26 75 1 0 27 76 1 0 27 77 1 0 28 78 1 6 30 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 31 83 1 0 32 84 1 1 33 85 1 0 34 86 1 6 35 87 1 0 37 88 1 0 37 89 1 0 37 90 1 0 38 91 1 0 38 92 1 0 38 93 1 0 39 94 1 6 40 95 1 0 40 96 1 0 41 97 1 0 41 98 1 0 43 99 1 0 43100 1 0 43101 1 0 44102 1 6 45103 1 6 46104 1 0 M END

Standard InCHIKey	CUOZRGBQTOSWAY-PWEPJYDOSA-N
Standard InCHI	InChI=1S/C36H58O10/c1-31(2)12-14-36(30(44)46-29-26(41)25(40)24(39)20(17-37)45-29)15-13-34(6)18(23(36)28(31)43)8-9-22-33(5)16-19(38)27(42)32(3,4)21(33)10-11-35(22,34)7/h8,19-29,37-43H,9-17H2,1-7H3/t19-,20-,21+,22-,23-,24-,25+,26-,27+,28+,29+,33+,34-,35-,36+/m1/s1
SMILES	CC1(C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	650.4	Volume:	662.503 ? Van der Waals volume.
Dense:	0.982	LogP:	2.23 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.527 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.326 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	177.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.177	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.492	Fsp³:	0.917
MCE-18:	133.507 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.878	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.059 ? 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:	0.159	Promiscuous compounds:	0.097

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.926	MDCK Permeability:	-5.065
Pgp-inhibitor:	0.0	Pgp-substrate:	0.152
PAMPA:	1.0 ? 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):	0.185
20% Bioavailability (F20%):	0.908	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.882	MRP1:	0.576
Plasma Protein Binding (PPB):	78.553%	Volume Distribution (VD):	-0.171
Fu:	16.294% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.075

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.458
HLM stability:	0.446 ? 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):

1.62

Half-life (T1/2):

2.575

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.033
Human Hepatotoxicity (H-HT):	0.622	Drug-induced Liver Injury (DILI):	0.566
AMES Toxicity:	0.861	Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.037	Skin Sensitization:	0.997
Carcinogencity:	0.42	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.034
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.985
Hematotoxicity:	0.571	Drug-induced Nephrotoxicity:	0.975
Genotoxicity:	0.454	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.549	Hek293 Cytotoxicity:	0.211
BCF:	1.243 ? 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:	3.643 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.327 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.506 ? 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
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650080]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10785422]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11277757]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	leaves	Khon Kaen, Thailand	2006-AUG	PMID[21265555]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9934464]
NPO30384	Combretum quadrangulare	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO45379	Pteleopsis suberosa Engl.et Diels	Genus	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Inhibition	3
Activity	4
IC50	1

Activity Type	# Activity
Individual protein	1
Cell line	4
Unchecked	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3809	Individual protein	Pancreatic alpha-amylase	Sus scrofa	Inhibition	=	7.2	%	PMID[27890380]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	11.1	%	PMID[29353722]
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	25.2	%	PMID[29353722]
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	24.5	%	PMID[29353722]
NPT993	Cell line	Hepatocyte	Mus musculus	Activity	=	15.6	%	PMID[29353722]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	36.1	%	PMID[27890380]
NPT28438	Unchecked	Unchecked	n.a.	IC50	n.a.	n.a.	n.a.	PMID[27890380]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	7.8	%	PMID[27890380]

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 NPC605954 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	21176
0.1-0.2	23185
0.2-0.3	4229
0.3-0.4	1006
0.4-0.5	171
0.5-0.6	64
0.6-0.7	18
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8784	High Similarity	NPC116794
0.8243	Intermediate Similarity	NPC191763
0.7848	Intermediate Similarity	NPC7870
0.7848	Intermediate Similarity	NPC310014
0.7848	Intermediate Similarity	NPC269315
0.7848	Intermediate Similarity	NPC75747
0.6988	Remote Similarity	NPC68419
0.6941	Remote Similarity	NPC128925
0.6941	Remote Similarity	NPC256798
0.6905	Remote Similarity	NPC271138
0.6905	Remote Similarity	NPC102914
0.6905	Remote Similarity	NPC110139
0.6905	Remote Similarity	NPC108709
0.6824	Remote Similarity	NPC220984
0.6786	Remote Similarity	NPC187056
0.6786	Remote Similarity	NPC606216
0.6786	Remote Similarity	NPC607023
0.6667	Remote Similarity	NPC65590
0.6667	Remote Similarity	NPC125923
0.6506	Remote Similarity	NPC167383
0.6429	Remote Similarity	NPC46388
0.6383	Remote Similarity	NPC161674
0.6207	Remote Similarity	NPC604133
0.6092	Remote Similarity	NPC199457
0.5977	Remote Similarity	NPC237503
0.596	Remote Similarity	NPC148417
0.5909	Remote Similarity	NPC37739
0.5843	Remote Similarity	NPC137917
0.5843	Remote Similarity	NPC212968
0.5684	Remote Similarity	NPC179434
0.5579	Remote Similarity	NPC29069
0.5567	Remote Similarity	NPC139894
0.5556	Remote Similarity	NPC473343
0.5534	Remote Similarity	NPC134835
0.5532	Remote Similarity	NPC47063
0.5521	Remote Similarity	NPC48499
0.551	Remote Similarity	NPC150400
0.55	Remote Similarity	NPC136313
0.5495	Remote Similarity	NPC48249
0.5481	Remote Similarity	NPC73318
0.5474	Remote Similarity	NPC204458
0.5474	Remote Similarity	NPC189884
0.5474	Remote Similarity	NPC90856
0.5474	Remote Similarity	NPC214484
0.5474	Remote Similarity	NPC269095
0.5474	Remote Similarity	NPC138334
0.5432	Remote Similarity	NPC259788
0.5432	Remote Similarity	NPC255589
0.5432	Remote Similarity	NPC307335
0.5432	Remote Similarity	NPC74855
0.5426	Remote Similarity	NPC209894
0.5417	Remote Similarity	NPC78046
0.5408	Remote Similarity	NPC235405
0.5385	Remote Similarity	NPC306746
0.5377	Remote Similarity	NPC96641
0.5377	Remote Similarity	NPC163183
0.5354	Remote Similarity	NPC473373
0.5354	Remote Similarity	NPC249848
0.5354	Remote Similarity	NPC107966
0.5333	Remote Similarity	NPC285576
0.53	Remote Similarity	NPC295371
0.53	Remote Similarity	NPC39211
0.5294	Remote Similarity	NPC30735
0.5253	Remote Similarity	NPC475516
0.5243	Remote Similarity	NPC10607
0.5243	Remote Similarity	NPC46665
0.52	Remote Similarity	NPC58448
0.5192	Remote Similarity	NPC475591
0.5192	Remote Similarity	NPC236870
0.5192	Remote Similarity	NPC68175
0.5192	Remote Similarity	NPC235438
0.5161	Remote Similarity	NPC64106
0.5149	Remote Similarity	NPC473884
0.5149	Remote Similarity	NPC157868
0.5146	Remote Similarity	NPC109588
0.5146	Remote Similarity	NPC104071
0.5111	Remote Similarity	NPC91583
0.5098	Remote Similarity	NPC475171
0.5098	Remote Similarity	NPC469946
0.5093	Remote Similarity	NPC80986
0.5049	Remote Similarity	NPC192791
0.5049	Remote Similarity	NPC75417
0.5049	Remote Similarity	NPC223301
0.5049	Remote Similarity	NPC242840
0.5049	Remote Similarity	NPC171544
0.5049	Remote Similarity	NPC112352
0.5048	Remote Similarity	NPC63159
0.5047	Remote Similarity	NPC281148

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC605954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7398
0.1-0.2	1667
0.2-0.3	81
0.3-0.4	4
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