NPASS Compound

Natural Product: NPC136771

Natural Product ID	NPC136771
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SRWJAXVAWDYXPA-ACNGEOCHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10350652
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 99108 0 0 0 0 0 0 0 0999 V2000 4.9007 1.7120 -1.3106 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3697 1.9670 -2.6029 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6384 2.4336 -2.8348 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4648 2.6537 -1.7600 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9940 2.3999 -0.4908 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7069 1.9258 -0.2458 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3592 1.7185 1.1863 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3790 0.6468 1.6507 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3375 -0.4263 0.5474 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9249 -0.8822 0.3633 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6942 -2.0835 -0.2251 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3982 -2.5323 -0.3859 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3221 -1.7659 0.0502 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5528 -0.5355 0.6538 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4142 0.2349 1.1528 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5120 0.8063 0.1344 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8260 2.0421 -0.4082 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0208 2.6252 -1.3596 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1095 2.0163 -1.8011 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4711 0.7897 -1.2932 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7095 0.1330 -1.7094 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2193 -0.8435 -0.7159 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2245 -2.1752 -0.9310 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7674 -3.0248 0.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2879 -2.4861 1.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2834 -1.1301 1.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7431 -0.3188 0.4456 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6895 1.0719 0.5671 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9712 1.9328 -0.5446 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3294 2.5201 -0.4072 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8059 2.9701 0.7983 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0580 3.5228 0.9495 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8836 3.6394 -0.1383 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4404 3.2002 -1.3587 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1668 2.6432 -1.4885 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2470 3.2972 -2.5032 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1488 4.1839 -0.0515 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8853 1.1452 -1.8023 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0355 0.2964 -1.7949 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8229 -3.3826 2.1346 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6931 -2.6929 -2.1055 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6501 0.2053 -0.3335 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9909 -1.0474 0.1992 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0515 -1.7597 0.8998 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4391 -3.0069 1.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5915 -3.1159 2.8529 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0304 -4.3393 3.3841 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3056 -5.4178 2.5643 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1500 -5.2969 1.2145 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7169 -4.0857 0.7064 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4159 -6.3577 0.3504 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7423 -6.6397 3.0778 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5619 -0.7865 1.9420 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5417 -0.1015 2.4471 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0105 -2.1303 -0.0677 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8744 2.6727 -2.7788 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9507 2.7782 -0.0433 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8438 -0.1107 0.8005 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1059 1.1065 1.3891 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7381 -2.8638 -0.6655 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0403 0.1232 2.8704 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7415 3.1245 -2.0145 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0852 2.6819 -4.1467 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9158 1.3441 -1.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6945 1.7858 -3.4506 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6736 2.5876 0.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4934 2.6560 1.7189 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4020 1.0590 1.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6876 -0.0425 -0.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0037 -1.2361 0.8923 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1931 -3.4874 -0.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7037 1.0486 1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2766 3.6079 -1.7884 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5964 -0.3158 -2.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7456 -4.0790 -0.1895 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6899 -0.7401 2.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2456 2.7862 -0.5163 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1707 2.8887 1.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3912 3.8687 1.9427 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8914 2.3285 -2.4701 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0572 3.8801 -2.5051 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2509 5.0982 0.3456 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8539 1.6808 -2.7382 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2068 -0.0371 -2.7083 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2439 -4.2469 1.8067 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9212 -2.2402 -2.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3974 -2.3212 3.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1524 -4.4331 4.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5907 -3.9831 -0.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0003 -6.4049 -0.5671 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0963 -7.4216 3.0680 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1353 -1.2468 2.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4968 0.8709 2.2742 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1180 3.6372 -2.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4746 3.2206 -0.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4555 -3.2048 -0.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5688 0.7820 3.4630 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5363 2.5178 -2.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3988 1.9111 -4.7386 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 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 34 36 1 0 33 37 1 0 29 38 1 0 38 39 1 0 25 40 1 0 23 41 1 0 20 42 2 0 42 43 1 0 43 44 1 0 44 45 1 1 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 49 51 1 0 48 52 1 0 44 53 1 0 53 54 1 0 44 55 1 0 19 56 1 0 17 57 1 0 14 58 2 0 58 59 1 0 11 60 1 0 8 61 1 0 4 62 1 0 3 63 1 0 6 1 1 0 59 7 1 0 58 10 1 0 55 13 1 0 53 15 1 0 42 16 1 0 50 45 1 0 38 21 1 0 27 22 1 0 35 30 1 0 1 64 1 0 2 65 1 0 5 66 1 0 7 67 1 1 8 68 1 1 9 69 1 0 9 70 1 0 12 71 1 0 15 72 1 1 18 73 1 0 21 74 1 6 24 75 1 0 26 76 1 0 29 77 1 6 31 78 1 0 32 79 1 0 35 80 1 0 36 81 1 0 37 82 1 0 38 83 1 6 39 84 1 0 40 85 1 0 41 86 1 0 46 87 1 0 47 88 1 0 50 89 1 0 51 90 1 0 52 91 1 0 53 92 1 1 54 93 1 0 56 94 1 0 57 95 1 0 60 96 1 0 61 97 1 0 62 98 1 0 63 99 1 0 M END

Standard InCHIKey	SRWJAXVAWDYXPA-ACNGEOCHSA-N
Standard InCHI	InChI=1S/C45H36O18/c46-18-10-27(54)33-31(11-18)60-41(16-2-5-21(48)25(52)8-16)39(58)37(33)34-28(55)13-29(56)35-38-36-32(62-45(44(38)59,63-43(34)35)17-3-6-22(49)26(53)9-17)14-23(50)19-12-30(57)40(61-42(19)36)15-1-4-20(47)24(51)7-15/h1-11,13-14,30,37-41,44,46-59H,12H2/t30-,37+,38+,39+,40+,41+,44+,45+/m0/s1
SMILES	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc3c([C@H]4c5c(cc(c([C@H]6c7c(cc(cc7O[C@H](c7ccc(c(c7)O)O)[C@@H]6O)O)O)c5O[C@](c5ccc(c(c5)O)O)([C@@H]4O)O3)O)O)c2O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	864.19	Volume:	812.079 ? Van der Waals volume.
Dense:	1.064	LogP:	1.544 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.708 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.39 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	54.0
TPSA:	320.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	14.0	Rings:	10.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.335	Fsp³:	0.2
MCE-18:	210.0 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.899	Fluc inhibitor:	0.036 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.645 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.631 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.576	Promiscuous compounds:	0.135

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.687	MDCK Permeability:	-4.782
Pgp-inhibitor:	0.0	Pgp-substrate:	0.05
PAMPA:	0.005 ? 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%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.971
Plasma Protein Binding (PPB):	91.73%	Volume Distribution (VD):	0.292
Fu:	12.325% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.011
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.971	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

6.718

Half-life (T1/2):

6.652

ADMET: Toxicity

hERG Blockers:	0.077	hERG Blockers (10um):	0.947
Human Hepatotoxicity (H-HT):	0.973	Drug-induced Liver Injury (DILI):	0.94
AMES Toxicity:	0.67	Rat Oral Acute Toxicity:	0.742
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.217	Respiratory Toxicity:	0.907
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.304
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.101
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.997
BCF:	1.211 ? 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:	4.019 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.314 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.696 ? 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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[15730255]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730255]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724861]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315967]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	leaf	n.a.	n.a.	PMID[20035557]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	atlantic-forest-soil	n.a.	PMID[20450206]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302965]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27684202]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288445]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26507	Galenia africana	Species	Aizoaceae	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 NPC136771 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	28330
0.1-0.2	19901
0.2-0.3	1400
0.3-0.4	121
0.4-0.5	27
0.5-0.6	28
0.6-0.7	16
0.7-0.8	0
0.8-0.85	8
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC86630
0.8667	High Similarity	NPC147743
0.8667	High Similarity	NPC4809
0.8667	High Similarity	NPC73517
0.863	High Similarity	NPC478616
0.863	High Similarity	NPC478339
0.8592	High Similarity	NPC272552
0.8592	High Similarity	NPC226108
0.8592	High Similarity	NPC322899
0.8571	High Similarity	NPC78074
0.8395	Intermediate Similarity	NPC478617
0.8228	Intermediate Similarity	NPC478337
0.8228	Intermediate Similarity	NPC478338
0.8148	Intermediate Similarity	NPC159526
0.8101	Intermediate Similarity	NPC106601
0.8101	Intermediate Similarity	NPC151474
0.8	Intermediate Similarity	NPC212614
0.8	Intermediate Similarity	NPC205613
0.7973	Intermediate Similarity	NPC46283
0.7973	Intermediate Similarity	NPC469944
0.7973	Intermediate Similarity	NPC134911
0.7922	Intermediate Similarity	NPC471404
0.7875	Intermediate Similarity	NPC478340
0.7867	Intermediate Similarity	NPC44192
0.7361	Intermediate Similarity	NPC58190
0.7361	Intermediate Similarity	NPC108811
0.7361	Intermediate Similarity	NPC170103
0.7361	Intermediate Similarity	NPC236202
0.7361	Intermediate Similarity	NPC262911
0.7361	Intermediate Similarity	NPC202742
0.726	Intermediate Similarity	NPC246202
0.726	Intermediate Similarity	NPC224161
0.726	Intermediate Similarity	NPC46335
0.726	Intermediate Similarity	NPC279406
0.726	Intermediate Similarity	NPC486519
0.72	Intermediate Similarity	NPC155564
0.6795	Remote Similarity	NPC226809
0.6625	Remote Similarity	NPC278548
0.6364	Remote Similarity	NPC294558
0.6364	Remote Similarity	NPC18185
0.6364	Remote Similarity	NPC263940
0.6203	Remote Similarity	NPC313116
0.6203	Remote Similarity	NPC603340
0.6184	Remote Similarity	NPC96576
0.6154	Remote Similarity	NPC484331
0.6087	Remote Similarity	NPC12326
0.6049	Remote Similarity	NPC70409
0.6049	Remote Similarity	NPC204770
0.6049	Remote Similarity	NPC600551
0.6049	Remote Similarity	NPC601980
0.6049	Remote Similarity	NPC602065
0.6049	Remote Similarity	NPC611024
0.5904	Remote Similarity	NPC600630
0.5904	Remote Similarity	NPC607896
0.5904	Remote Similarity	NPC611369
0.5882	Remote Similarity	NPC20050
0.5811	Remote Similarity	NPC178054
0.5783	Remote Similarity	NPC211561
0.5684	Remote Similarity	NPC484330
0.5632	Remote Similarity	NPC306267
0.5625	Remote Similarity	NPC185231
0.5432	Remote Similarity	NPC601999
0.5412	Remote Similarity	NPC601997
0.5412	Remote Similarity	NPC609211
0.5412	Remote Similarity	NPC610665
0.5393	Remote Similarity	NPC135021
0.5385	Remote Similarity	NPC9309
0.5342	Remote Similarity	NPC261619
0.5342	Remote Similarity	NPC61477
0.5342	Remote Similarity	NPC78770
0.5342	Remote Similarity	NPC219876
0.5342	Remote Similarity	NPC126029
0.5342	Remote Similarity	NPC15658
0.5287	Remote Similarity	NPC302549
0.5181	Remote Similarity	NPC20757
0.5181	Remote Similarity	NPC227516
0.5119	Remote Similarity	NPC184245
0.5119	Remote Similarity	NPC187801
0.5119	Remote Similarity	NPC610920
0.506	Remote Similarity	NPC82917

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC136771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5967
0.1-0.2	3161
0.2-0.3	14
0.3-0.4	6
0.4-0.5	0
0.5-0.6	2
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
0.5342	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.5342	Remote Similarity	NPD1613	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