NPASS Compound

Natural Product: NPC110693

Natural Product ID	NPC110693
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LVYIOIIDBKGTEP-WHKAJQBWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	23659788
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 77 80 0 0 0 0 0 0 0 0999 V2000 -6.6327 0.6391 -1.6627 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4519 1.0107 -0.8602 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2523 0.5498 0.4063 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0375 1.0185 1.0450 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9600 0.1434 1.4676 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1760 -0.7016 0.5877 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9243 -1.7512 -0.2085 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1348 -0.1743 -0.2944 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4340 0.8125 -1.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0497 1.3185 -1.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8787 0.5402 -0.9736 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2657 0.9613 -0.7809 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9473 -0.1956 -0.0558 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3170 -0.2179 1.3212 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8469 -0.5369 1.1987 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0980 0.4254 0.3487 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0979 1.7774 0.9306 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4175 -0.1573 -0.0501 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9269 0.1777 1.3537 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9415 -1.5903 -0.2893 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4493 -1.6147 -0.1850 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1141 -0.6505 -1.1124 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5577 0.7407 -1.0544 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0840 0.6529 -1.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4240 1.2988 -1.9878 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9702 1.2330 -2.0284 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3719 1.4084 -3.1148 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4675 -0.5681 -0.7277 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3465 -0.2659 0.9338 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9563 -1.6928 1.1381 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9429 0.2644 2.2187 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7581 -0.4705 -1.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4999 0.9894 -2.7032 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5732 1.1259 -1.2960 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7113 1.6722 -1.2830 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6469 1.9831 0.5633 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4148 1.5000 2.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2178 0.7959 2.0284 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3443 -0.4862 2.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5699 -1.3674 1.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7328 -1.3052 -0.8044 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2505 -2.5982 0.4247 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2340 -2.2206 -0.9718 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7162 -1.0812 -0.8455 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9970 1.6988 -1.1021 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9087 0.3304 -2.2281 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0750 1.1348 -2.8931 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0807 2.3938 -1.5957 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8977 -0.5268 -1.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4378 1.8385 -0.1209 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5834 -1.1413 -0.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4748 0.7633 1.8103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7503 -0.9967 1.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7791 -1.5414 0.7239 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4138 -0.6580 2.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7008 2.5265 0.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0303 1.7673 2.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0326 2.2794 0.5859 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7677 -0.7359 1.9616 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4860 1.0855 1.7600 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0458 0.3077 1.3234 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5399 -2.2655 0.4797 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6708 -1.9232 -1.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8078 -1.5276 0.8649 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7563 -2.6444 -0.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0909 -0.9952 -2.1495 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9435 1.3274 -0.1962 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9331 1.2738 -1.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9664 1.9038 -2.7454 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0000 -0.2107 -1.4987 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2479 -0.2356 0.2193 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0891 -1.8750 1.7831 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7333 -2.2135 0.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7929 -2.2763 1.6397 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8547 -0.3451 2.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2559 0.0576 3.0555 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2707 1.3081 2.1517 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 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 1 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 22 28 1 0 3 29 1 0 29 30 1 0 29 31 1 0 16 8 1 0 24 18 1 0 16 11 1 0 26 12 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 0 4 36 1 0 4 37 1 0 5 38 1 0 5 39 1 0 6 40 1 1 7 41 1 0 7 42 1 0 7 43 1 0 8 44 1 6 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 6 12 50 1 1 13 51 1 6 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 17 56 1 0 17 57 1 0 17 58 1 0 19 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 22 66 1 6 23 67 1 0 23 68 1 0 25 69 1 0 28 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 M END

Standard InCHIKey	LVYIOIIDBKGTEP-WHKAJQBWSA-N
Standard InCHI	InChI=1S/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-27-25(13-15-29(23,24)6)28(5)14-12-22(30)16-21(28)17-26(27)31/h7,17-19,22-25,27,30H,8-16H2,1-6H3/b20-7-/t19-,22+,23-,24+,25+,27+,28+,29-/m1/s1
SMILES	C/C=C(/CC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H](CC1=CC3=O)O)C(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	426.35	Volume:	485.585 ? Van der Waals volume.
Dense:	0.878	LogP:	5.729 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.361 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.341 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.475	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.638	Fsp³:	0.828
MCE-18:	70.792 ? 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:	0.96	Fluc inhibitor:	0.047 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.4	Promiscuous compounds:	0.286

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.062	MDCK Permeability:	-4.928
Pgp-inhibitor:	0.31	Pgp-substrate:	0.006
PAMPA:	0.017 ? 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%):	0.016	30% Bioavailability (F30%):	0.625
50% Bioavailability (F50%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.013
Plasma Protein Binding (PPB):	95.927%	Volume Distribution (VD):	-0.207
Fu:	4.12% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.664
BSEP inhibitor:	0.574

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.31	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.598
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.334 ? 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):

11.643

Half-life (T1/2):

0.549

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.314
Human Hepatotoxicity (H-HT):	0.864	Drug-induced Liver Injury (DILI):	0.758
AMES Toxicity:	0.3	Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.219	Skin Sensitization:	0.995
Carcinogencity:	0.861	Eye Corrosion:	0.207
Eye Irritation:	0.984	Respiratory Toxicity:	0.865
Drug-induced Neurotoxicity:	0.049	Ototoxicity:	0.31
Hematotoxicity:	0.345	Drug-induced Nephrotoxicity:	0.565
Genotoxicity:	0.094	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.175	Hek293 Cytotoxicity:	0.468
BCF:	2.66 ? 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:	4.475 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.285 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.118 ? 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
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	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 NPC110693 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	15160
0.1-0.2	28827
0.2-0.3	5479
0.3-0.4	287
0.4-0.5	61
0.5-0.6	25
0.6-0.7	4
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
0.7963	Intermediate Similarity	NPC31564
0.7963	Intermediate Similarity	NPC145879
0.7636	Intermediate Similarity	NPC26959
0.7241	Intermediate Similarity	NPC268406
0.7193	Intermediate Similarity	NPC474778
0.7193	Intermediate Similarity	NPC474733
0.7049	Intermediate Similarity	NPC599942
0.6949	Remote Similarity	NPC186688
0.678	Remote Similarity	NPC474732
0.678	Remote Similarity	NPC58063
0.6562	Remote Similarity	NPC489072
0.5833	Remote Similarity	NPC134847
0.5593	Remote Similarity	NPC162742
0.5593	Remote Similarity	NPC304309
0.5593	Remote Similarity	NPC470228
0.5574	Remote Similarity	NPC84694
0.5574	Remote Similarity	NPC143182
0.5556	Remote Similarity	NPC472265
0.5556	Remote Similarity	NPC59453
0.55	Remote Similarity	NPC34019
0.5333	Remote Similarity	NPC81306
0.5333	Remote Similarity	NPC282593
0.5323	Remote Similarity	NPC230301
0.5323	Remote Similarity	NPC198968
0.5323	Remote Similarity	NPC285893
0.5246	Remote Similarity	NPC22105
0.5246	Remote Similarity	NPC107059
0.5231	Remote Similarity	NPC309603
0.5231	Remote Similarity	NPC474752
0.5231	Remote Similarity	NPC474683
0.5161	Remote Similarity	NPC136188
0.5161	Remote Similarity	NPC28657
0.5161	Remote Similarity	NPC474216
0.5079	Remote Similarity	NPC28862
0.5077	Remote Similarity	NPC33913
0.5072	Remote Similarity	NPC234335

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC110693 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5775
0.1-0.2	3069
0.2-0.3	260
0.3-0.4	42
0.4-0.5	1
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
0.5323	Remote Similarity	NPD7339	Approved
0.5161	Remote Similarity	NPD6942	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