NPASS Compound

Natural Product: NPC93033

Natural Product ID	NPC93033
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LCFUUGFUQQAYMY-CJAQKTMASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	12444466
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 76 79 0 0 0 0 0 0 0 0999 V2000 6.5583 -1.5667 -0.8987 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3058 -0.0682 -0.8036 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8636 0.1422 -0.2301 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9037 -0.4848 -1.1454 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4484 -0.4822 -0.8411 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9742 -1.2458 0.3508 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4867 -0.8123 1.6814 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5252 -1.6105 0.2964 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1859 -2.4374 1.5073 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0628 -1.7898 2.1311 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6726 -1.2579 0.8773 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8238 -0.3536 0.9839 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3912 -0.2682 -0.4428 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3187 0.3850 -1.2760 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9921 -0.2704 -1.1906 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4821 -0.5253 0.1991 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2323 0.7286 0.9403 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6794 0.4484 -0.5357 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4529 1.9372 -0.7159 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4490 -0.0185 -1.7623 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7444 0.6915 -1.9480 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5045 0.9283 -0.7138 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9478 0.7265 0.4940 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5714 0.2660 0.6201 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2042 -0.2884 1.7603 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8482 -0.7695 1.9495 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6105 -1.5113 2.9183 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6946 1.6434 -0.0297 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7699 2.0432 0.9823 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0508 2.3801 -1.3063 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9195 -2.0505 -0.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2993 -1.9491 -1.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5992 -1.7550 -0.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4102 0.4201 -1.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9744 0.3271 -0.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9377 -0.3139 0.7548 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2712 -1.5746 -1.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0055 -0.0157 -2.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1592 0.6167 -0.8079 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9603 -0.8429 -1.7843 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4659 -2.2767 0.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8905 0.2190 1.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7226 -0.8798 2.5085 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3249 -1.4495 2.0922 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3818 -2.2629 -0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9478 -2.5803 2.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1083 -3.4913 1.1902 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6284 -2.6338 2.5712 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8216 -1.0697 2.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8904 -2.1170 0.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5754 0.7030 1.2269 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4977 -1.3157 -0.7870 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2583 1.4870 -1.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6592 0.3329 -2.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2848 0.3441 -1.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0449 -1.2617 -1.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6973 0.7320 1.9743 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8104 1.5484 0.4149 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.0951 1.0194 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7671 2.2524 0.1053 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3856 2.5021 -0.5721 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0683 2.1849 -1.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6677 -1.0948 -1.5938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8502 0.1030 -2.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3928 0.0508 -2.6083 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6480 1.6548 -2.4897 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5245 1.2694 -0.8075 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5236 0.9062 1.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9080 -0.4041 2.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7112 1.8729 0.3360 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3698 2.8696 1.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0415 1.2008 1.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6814 2.4257 0.4810 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5914 1.8571 -2.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1372 2.3831 -1.4021 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6490 3.4216 -1.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 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 1 13 18 1 0 18 19 1 6 18 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 3 28 1 0 28 29 1 0 28 30 1 0 16 8 1 0 24 18 1 0 16 11 1 0 26 12 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 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 6 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 6 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 11 50 1 6 12 51 1 1 13 52 1 6 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 17 57 1 0 17 58 1 0 17 59 1 0 19 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 22 67 1 0 23 68 1 0 25 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 M END

Standard InCHIKey	LCFUUGFUQQAYMY-CJAQKTMASA-N
Standard InCHI	InChI=1S/C29H46O/c1-7-21(19(2)3)12-11-20(4)23-13-14-24-27-25(15-17-29(23,24)6)28(5)16-9-8-10-22(28)18-26(27)30/h8,10,18-21,23-25,27H,7,9,11-17H2,1-6H3/t20-,21-,23-,24+,25+,27+,28+,29-/m1/s1
SMILES	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CCC=CC1=CC3=O)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	410.35	Volume:	476.795 ? Van der Waals volume.
Dense:	0.861	LogP:	7.378 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.885 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.487 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
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:	0.433	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.611	Fsp³:	0.828
MCE-18:	66.226 ? 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:	0.859	Fluc inhibitor:	0.323 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.599	Promiscuous compounds:	0.326

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.107	MDCK Permeability:	-4.944
Pgp-inhibitor:	0.007	Pgp-substrate:	0.053
PAMPA:	0.013 ? 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%):	0.008	30% Bioavailability (F30%):	0.525
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357	MRP1:	0.04
Plasma Protein Binding (PPB):	97.818%	Volume Distribution (VD):	-0.176
Fu:	2.333% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.135
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.981
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.962
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.719	CYP2D6-substrate:	0.82
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

10.738

Half-life (T1/2):

0.158

ADMET: Toxicity

hERG Blockers:	0.224	hERG Blockers (10um):	0.542
Human Hepatotoxicity (H-HT):	0.748	Drug-induced Liver Injury (DILI):	0.561
AMES Toxicity:	0.218	Rat Oral Acute Toxicity:	0.176
Maximum Recommended Daily Dose:	0.333	Skin Sensitization:	0.998
Carcinogencity:	0.69	Eye Corrosion:	0.805
Eye Irritation:	0.978	Respiratory Toxicity:	0.885
Drug-induced Neurotoxicity:	0.345	Ototoxicity:	0.288
Hematotoxicity:	0.548	Drug-induced Nephrotoxicity:	0.467
Genotoxicity:	0.014	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.706	Hek293 Cytotoxicity:	0.597
BCF:	3.494 ? 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:	5.113 ? 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:	6.007 ? 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
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00579992]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17125224]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	stems, roots, and leaves	Da-Han Mountain, Kaohsiung, Taiwan	2004-OCT	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17417907]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19829679]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506820]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[21087019]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21469692]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21469692]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22314230]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23521110]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[26238320]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[27400231]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29775308]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30931559]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31664789]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36441179]
NPO64536	Barleria albostellata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446958]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37513251]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37569279]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38868673]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38999684]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39220961]
NPO28701	Salvia lanigera	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[8824952]
NPO27927	Alligator sinensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9287418]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834167]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24010	Buglossoides arvensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23674	Jatropha curcas	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23092	Ammodendron karelinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27927	Alligator sinensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28414	Medicosma fareana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17288	Piliostigma thonningii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28213	Humicola grisea	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28855	Salix petiolaris	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28842	Oscillatoria raoi	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28701	Salvia lanigera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28065	Pentachondra pumila	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28145	Dendrodoris limbata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24144	Ophiomastix mixta	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23674	Jatropha curcas	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23674	Jatropha curcas	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27988	Salvia pisidica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24010	Buglossoides arvensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28932	Myrrhis odorata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24010	Buglossoides arvensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28337	Pimpinella peregrina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27968	Phoma linga	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28701	Salvia lanigera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28559	Julbernardia globifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28842	Oscillatoria raoi	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28623	Phlox decussata	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28213	Humicola grisea	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28435	Solanum crinitum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28127	Ursinia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28932	Myrrhis odorata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28145	Dendrodoris limbata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23092	Ammodendron karelinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21547	Crinum giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28545	Scymnorhinus lichia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28578	Uperoleia inundata	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28280	Cetraria komarovii	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28414	Medicosma fareana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24144	Ophiomastix mixta	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27880	Mimusops laurifolia	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28739	Othonna macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28112	Amauris niavius	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27927	Alligator sinensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28489	Euphrasia regelii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28196	Brachylaena perrieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27988	Salvia pisidica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28384	Ascotricha chartarum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28065	Pentachondra pumila	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28266	Phlomis ostrowskiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28501	Hortonia angustifolia	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28233	Diplotropis ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17288	Piliostigma thonningii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28855	Salix petiolaris	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11872	Eleutherococcus senticosus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23674	Jatropha curcas	Species	Euphorbiaceae	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
NPO64536	Barleria albostellata	n.a.	Stems	1.51	n.a.	n.a.	%	PMID[37446958]

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 NPC93033 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	21612
0.1-0.2	26314
0.2-0.3	1859
0.3-0.4	56
0.4-0.5	15
0.5-0.6	2
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6481	Remote Similarity	NPC469769
0.5932	Remote Similarity	NPC145879
0.541	Remote Similarity	NPC56525

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC93033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6687
0.1-0.2	2349
0.2-0.3	108
0.3-0.4	6
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