NPASS Compound

Natural Product: NPC37454

Natural Product ID	NPC37454
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TZYOKXQYQQXUCI-BUUZRMBISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10101175
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 94 98 0 0 0 0 0 0 0 0999 V2000 4.2959 0.3864 1.2947 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6642 0.3995 2.4474 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3548 -0.2714 2.6746 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3917 -0.7558 4.1099 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1881 0.6746 2.5030 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6160 0.6258 1.0936 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2365 -0.6849 0.5914 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1466 -1.0043 0.1754 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9698 -1.3820 1.4127 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9821 -2.2232 -0.7348 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4659 -3.4302 -0.0466 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6847 -3.1705 0.8892 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7541 -1.8005 1.4659 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1637 -1.4790 1.8020 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1519 -2.0683 1.4598 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0929 -1.7450 2.7070 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9113 -3.6317 0.3699 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6259 -4.6949 0.8692 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1012 -5.2574 1.8585 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9152 -5.1139 0.2565 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4430 -4.2750 0.4821 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0424 -2.4781 -1.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3085 -3.0973 -1.2437 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4242 -3.5410 -2.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2839 -1.2952 -2.6263 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7073 0.0146 -2.0446 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9777 -0.0148 -0.5593 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2955 1.1746 0.0489 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5643 1.5547 0.3723 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4614 0.7413 0.0625 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9469 2.7892 1.0272 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2961 3.0391 1.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6941 4.1869 1.8725 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8230 5.1571 2.3130 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4850 4.9229 2.0982 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0630 3.7564 1.4656 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3798 0.1713 -2.3773 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0935 1.1594 -3.2259 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7386 1.9509 -3.7045 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5484 1.1998 -3.5020 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7674 -1.4124 -3.8894 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5419 1.3600 0.3139 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3610 2.5906 -0.2376 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2182 3.0588 0.0144 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2545 3.3800 -1.0238 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8932 4.6187 -1.4796 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7661 5.3938 -2.2519 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0094 4.9092 -2.5618 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3947 3.6653 -2.1141 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5043 2.9212 -1.3498 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2457 0.8743 1.1353 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8480 -0.1297 0.4587 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0917 0.9307 3.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7152 -1.5640 4.3518 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1097 0.1464 4.7303 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4500 -0.9609 4.4189 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4442 0.4761 3.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5908 1.6852 2.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2752 1.2722 1.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8649 -0.8575 -0.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8416 -2.4009 1.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0706 -1.2809 1.1327 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8661 -0.6770 2.2317 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1068 -1.9074 -1.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0285 -4.0816 -0.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5070 -3.8616 1.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1126 -2.6901 3.0390 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7610 -5.2840 -0.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1805 -6.0960 0.7006 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7362 -4.4169 0.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1390 -4.7369 1.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1546 -2.4139 -1.5579 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4210 -3.2395 -0.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5818 -4.0601 -1.7714 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4791 -4.5403 -2.2303 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9663 -3.5127 -3.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3943 -3.1829 -2.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3834 -1.1849 -2.7101 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3851 0.7801 -2.5044 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0068 -0.5510 -0.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0081 2.3065 0.9222 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7601 4.3738 2.0436 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1813 6.0534 2.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7667 5.6663 2.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0165 3.6167 1.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7490 0.6524 -4.4567 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1360 0.7462 -2.6817 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9181 2.2278 -3.6695 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4727 -1.3315 -4.6034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9343 5.0534 -1.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5018 6.3705 -2.6201 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6907 5.4787 -3.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3831 3.3206 -2.3812 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8685 1.9557 -1.0385 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 1 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 13 16 1 1 12 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 11 21 1 0 10 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 26 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 25 41 1 0 6 42 1 0 42 43 1 0 43 44 2 0 43 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 14 3 1 0 36 31 1 0 50 45 1 0 13 7 1 0 27 8 1 0 1 51 1 0 1 52 1 0 2 53 1 0 4 54 1 0 4 55 1 0 4 56 1 0 5 57 1 0 5 58 1 0 6 59 1 1 7 60 1 6 9 61 1 0 9 62 1 0 9 63 1 0 10 64 1 6 11 65 1 6 12 66 1 1 16 67 1 0 20 68 1 0 20 69 1 0 20 70 1 0 21 71 1 0 23 72 1 0 23 73 1 0 23 74 1 0 24 75 1 0 24 76 1 0 24 77 1 0 25 78 1 6 26 79 1 6 27 80 1 6 32 81 1 0 33 82 1 0 34 83 1 0 35 84 1 0 36 85 1 0 40 86 1 0 40 87 1 0 40 88 1 0 41 89 1 0 46 90 1 0 47 91 1 0 48 92 1 0 49 93 1 0 50 94 1 0 M END

Standard InCHIKey	TZYOKXQYQQXUCI-BUUZRMBISA-N
Standard InCHI	InChI=1S/C38H44O12/c1-8-36(6)19-24(49-32(43)22-15-11-9-12-16-22)27-37(7)28(25(41)30(48-21(3)40)38(27,46)34(36)45)35(4,5)29(42)26(47-20(2)39)31(37)50-33(44)23-17-13-10-14-18-23/h8-18,24-31,41-42,46H,1,19H2,2-7H3/t24-,25+,26+,27-,28+,29-,30-,31+,36+,37-,38-/m1/s1
SMILES	C=C[C@@]1(C)C[C@H]([C@@H]2[C@]3(C)[C@@H]([C@@H]([C@H]([C@]2(C1=O)O)OC(=O)C)O)C(C)(C)[C@@H]([C@@H]([C@@H]3OC(=O)c1ccccc1)OC(=O)C)O)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	692.28	Volume:	696.867 ? Van der Waals volume.
Dense:	0.993	LogP:	2.99 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.933 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.857 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	34.0
TPSA:	182.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.219	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.297	Fsp³:	0.5
MCE-18:	145.158 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.676	Fluc inhibitor:	0.03 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.028 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.225	Promiscuous compounds:	0.212

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.679	MDCK Permeability:	-5.112
Pgp-inhibitor:	0.571	Pgp-substrate:	0.998
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):	0.0
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015	MRP1:	1.0
Plasma Protein Binding (PPB):	84.209%	Volume Distribution (VD):	-0.017
Fu:	14.282% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.945	BCRP inhibitor:	0.017
BSEP inhibitor:	0.915

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.067	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

3.662

Half-life (T1/2):

1.459

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.393
Human Hepatotoxicity (H-HT):	0.048	Drug-induced Liver Injury (DILI):	0.409
AMES Toxicity:	0.184	Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.197	Skin Sensitization:	0.995
Carcinogencity:	0.514	Eye Corrosion:	0.008
Eye Irritation:	0.64	Respiratory Toxicity:	0.172
Drug-induced Neurotoxicity:	0.063	Ototoxicity:	0.244
Hematotoxicity:	0.089	Drug-induced Nephrotoxicity:	0.836
Genotoxicity:	0.744	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.224	Hek293 Cytotoxicity:	0.28
BCF:	0.492 ? 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:	3.521 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.423 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.623 ? 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
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374950]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473439]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141863]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[12467611]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	aerial parts	Bangdung, Indonesia	2000-Aug	PMID[12608860]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15104497]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18076141]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22165973]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26473275]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28898076]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[31713425]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32933154]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33081385]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34847783]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36671383]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38202742]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23062	Melibe leonina	Species	Dendronotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21545	Maytenus guianensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19152	Empetrum nigrum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20726	Ophioplocus japonicus	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21807	Lindera umbellata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21384	Tetraria capillaris	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22462	Chlorophytum malayense	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21881	Stephania succifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22900	Orthosiphon stamineus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21140	Igernella notabilis	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23226	Satureja montana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21680	Saussurea triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22518	Gnetum cleistostachyum	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22952	Senecio grandiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22717	Pinus thunbergii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5877	Morus yunnanensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19451	Salvia prionitis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23141	Angelica ursina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23101	Ircinia aruensis	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20100	Ephedra lomatolepis	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22773	Teucrium alyssifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20964	Picradeniopsis oppositifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21944	Laurencia mariannensis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7320	Nicotiana gossei	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21745	Phleum africanum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22197	Eriogaster lanestris	Species	Lasiocampidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23183	Pinus halepensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22911	Enterococcus faecalis	Species	Enterococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22137	Vernonia serratuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22015	Clausena indica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22395	Ardisia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3549	Euonymus maackii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22071	Gentiana olivieri	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23062	Melibe leonina	Species	Dendronotidae	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 NPC37454 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	8005
0.1-0.2	38264
0.2-0.3	3130
0.3-0.4	426
0.4-0.5	13
0.5-0.6	15
0.6-0.7	2
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	Natural Product ID
0.7361	Intermediate Similarity	NPC257213
0.7361	Intermediate Similarity	NPC478502
0.6986	Remote Similarity	NPC304876
0.6026	Remote Similarity	NPC60509
0.5949	Remote Similarity	NPC198455
0.5897	Remote Similarity	NPC265395
0.5823	Remote Similarity	NPC249471
0.575	Remote Similarity	NPC228204
0.5696	Remote Similarity	NPC478503
0.5696	Remote Similarity	NPC237549
0.5488	Remote Similarity	NPC472022
0.5488	Remote Similarity	NPC473414
0.5476	Remote Similarity	NPC472005
0.5309	Remote Similarity	NPC182869
0.5301	Remote Similarity	NPC256142
0.5244	Remote Similarity	NPC472030
0.5185	Remote Similarity	NPC48568
0.5122	Remote Similarity	NPC242262
0.5062	Remote Similarity	NPC158333

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC37454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3101
0.1-0.2	5876
0.2-0.3	173
0.3-0.4	0
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