NPASS Compound

Natural Product: NPC309318

Natural Product ID	NPC309318
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RTLUSWHIKFIQFU-DALQDKCESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5356634
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

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

Chemical Representations

RDKit 3D 78 81 0 0 0 0 0 0 0 0999 V2000 -7.0909 0.7380 1.9943 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2164 0.7024 0.8039 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8325 0.1475 0.9777 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1231 0.2597 -0.3735 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9676 0.9171 -0.5005 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2551 1.0461 -1.7865 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4718 2.4681 -2.2492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9193 0.5033 -1.8878 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3662 0.7249 -3.2944 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0353 0.1169 -3.1373 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2284 -0.1320 -1.6852 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6056 0.1290 -1.1796 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5583 -0.7793 -1.9134 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2639 -1.7534 -1.0306 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8565 -1.1327 0.2042 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1560 -2.2616 1.1702 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8115 -1.7029 2.3563 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6650 -2.3389 2.9338 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4097 -0.3550 2.8276 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9976 -0.1069 2.3395 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9542 -0.0974 0.8316 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4481 1.2932 0.4103 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5889 -0.2831 0.2783 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5104 0.3678 1.0592 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1975 0.5509 0.3901 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2180 0.8626 -1.0595 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8324 2.2111 -1.2848 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8968 -1.3383 1.2239 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4743 -1.8973 1.3753 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7513 -1.7900 2.3538 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0610 0.1983 1.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6559 0.4882 2.9571 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4742 1.8131 2.1238 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7373 0.1976 -0.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0791 1.7570 0.4000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2668 0.6760 1.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5248 -0.1840 -1.2690 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5880 1.3618 0.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8700 0.4450 -2.5389 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2264 3.1724 -1.4274 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5923 2.6044 -2.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0591 2.7135 -3.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0190 -0.6289 -1.8348 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9234 0.1019 -4.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3191 1.7661 -3.5976 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0830 -0.8679 -3.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8056 0.7598 -3.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9046 -1.1447 -1.4292 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9216 1.1560 -1.3476 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0407 -1.3650 -2.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3510 -0.1979 -2.4669 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6276 -2.6394 -0.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1237 -2.1713 -1.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8392 -0.6805 -0.0846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1708 -2.6681 1.4864 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7335 -3.0362 0.6540 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1411 0.3623 2.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4327 -0.2829 3.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3731 -0.9352 2.7566 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6778 0.8865 2.6935 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8208 1.2660 -0.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6801 2.0701 0.5986 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3230 1.5922 1.0371 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3652 -1.3907 0.2654 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3201 -0.2942 1.9586 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8442 1.3360 1.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3404 1.3430 0.9701 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4248 -0.3732 0.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5568 2.3844 -0.4604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1534 3.0571 -1.2758 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4394 2.2386 -2.2348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2913 -1.8038 0.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2119 -1.9609 2.4507 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8154 -1.1991 0.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3947 -2.8864 0.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8325 -1.7421 2.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4337 -1.4438 3.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5597 -2.9207 2.4194 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 2 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 3 28 1 0 28 29 1 0 28 30 1 0 26 8 1 0 26 11 1 0 23 12 1 0 21 15 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 2 35 1 0 3 36 1 1 4 37 1 0 5 38 1 0 6 39 1 6 7 40 1 0 7 41 1 0 7 42 1 0 8 43 1 6 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 6 12 49 1 1 13 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 6 16 55 1 0 16 56 1 0 19 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 22 61 1 0 22 62 1 0 22 63 1 0 23 64 1 6 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	RTLUSWHIKFIQFU-DALQDKCESA-N
Standard InCHI	InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,19-22,24-27H,7,10-18H2,1-6H3/b9-8+/t20-,21-,22-,24+,25-,26+,27+,28+,29-/m1/s1
SMILES	CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.37	Volume:	479.432 ? Van der Waals volume.
Dense:	0.86	LogP:	6.706 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.743 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.499 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	17.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.417	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.537	Fsp³:	0.897
MCE-18:	69.709 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.958	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.675	Promiscuous compounds:	0.077

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152	MDCK Permeability:	-5.027
Pgp-inhibitor:	0.832	Pgp-substrate:	0.0
PAMPA:	0.001 ? 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%):	0.052	30% Bioavailability (F30%):	0.284
50% Bioavailability (F50%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.029
Plasma Protein Binding (PPB):	98.639%	Volume Distribution (VD):	0.09
Fu:	0.797% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.36
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.837
CYP2C19-inhibitor:	0.707	CYP2C19-substrate:	0.009
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.771 ? 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):

11.483

Half-life (T1/2):

0.235

ADMET: Toxicity

hERG Blockers:	0.224	hERG Blockers (10um):	0.469
Human Hepatotoxicity (H-HT):	0.713	Drug-induced Liver Injury (DILI):	0.664
AMES Toxicity:	0.17	Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.663	Skin Sensitization:	0.95
Carcinogencity:	0.904	Eye Corrosion:	0.366
Eye Irritation:	0.964	Respiratory Toxicity:	0.963
Drug-induced Neurotoxicity:	0.489	Ototoxicity:	0.475
Hematotoxicity:	0.671	Drug-induced Nephrotoxicity:	0.574
Genotoxicity:	0.189	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.358	Hek293 Cytotoxicity:	0.786
BCF:	2.875 ? 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:	4.535 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.076 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.191 ? 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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 17014425]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/bab.1236]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00714468]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2010.09.006]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	DOI[10.1021/jf00055a023]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11040054]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[11539687]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713418]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724856]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19900811]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	husk	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21574561]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[23292602]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	anomalous fruits	n.a.	n.a.	PMID[25442304]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29762032]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8368081]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	pollen	n.a.	PMID[8987503]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31185	Phragmites communis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Cob	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Husk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31185	Phragmites communis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31185	Phragmites communis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26785	Taraxacum mongolicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20554	Astragalus complanatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26785	Taraxacum mongolicum	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 NPC309318 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	24445
0.1-0.2	23727
0.2-0.3	1544
0.3-0.4	118
0.4-0.5	15
0.5-0.6	7
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6522	Remote Similarity	NPC143597
0.6522	Remote Similarity	NPC151464
0.6327	Remote Similarity	NPC184819
0.5714	Remote Similarity	NPC288296
0.5714	Remote Similarity	NPC53245
0.5455	Remote Similarity	NPC115023
0.5283	Remote Similarity	NPC324607
0.5283	Remote Similarity	NPC321732
0.5179	Remote Similarity	NPC182815
0.5179	Remote Similarity	NPC607894

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC309318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7047
0.1-0.2	1929
0.2-0.3	151
0.3-0.4	21
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
0.5882	Remote Similarity	NPD4789	Approved
0.5283	Remote Similarity	NPD3698	Phase 2

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