NPASS Compound

Natural Product: NPC57233

Natural Product ID	NPC57233
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	UBLNLUPLUKPSPP-QGTGJCAVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	13458955
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 83 87 0 0 0 0 0 0 0 0999 V2000 4.5826 2.5950 -0.7563 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4090 1.9218 0.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7570 2.0618 1.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1413 0.4605 0.4727 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3511 -0.1349 -0.2475 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7967 -0.9784 -1.3847 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4218 -1.3266 -0.8049 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6520 -2.2782 0.3048 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4981 -1.9203 -1.8105 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1208 -1.9606 -1.2050 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6894 -0.6548 -0.6222 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5065 0.3197 -1.7572 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6671 -0.0521 0.3467 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1448 1.2358 0.8650 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2891 1.4038 1.0469 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1979 0.4954 0.3081 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6255 0.5089 0.7754 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8591 0.1137 2.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1224 1.9353 0.5840 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6035 2.0566 0.6709 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2248 1.2436 -0.4263 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8371 -0.2050 -0.2339 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3479 -0.9278 -1.4946 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5475 -0.8287 0.9197 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3671 -0.3544 -0.2406 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9165 -1.7844 -0.1646 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4658 -1.8030 -0.6501 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6069 -0.8749 0.1557 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3144 -1.5414 1.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6192 1.3159 -0.2943 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9934 0.0611 -0.3579 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6935 3.2548 -0.9788 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6338 1.8770 -1.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4485 3.2959 -0.7402 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7026 2.4952 1.1756 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6014 2.0450 0.6255 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7614 3.0074 1.9367 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7869 1.2409 2.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1087 0.0348 1.4912 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9870 0.6315 -0.7090 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9785 -0.7281 0.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3405 -1.9312 -1.5070 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7136 -0.4104 -2.3134 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6863 -2.7313 0.2934 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5018 -1.9024 1.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9741 -3.1712 0.1995 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8128 -2.9983 -1.9353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5427 -1.4847 -2.8107 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4157 -2.1702 -2.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0491 -2.8224 -0.5450 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3884 0.1543 -2.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5805 1.3763 -1.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3756 0.0950 -2.3941 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8338 -0.7356 1.2114 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6627 1.4294 1.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5589 2.0512 0.1994 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5676 1.3609 2.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5807 2.4615 0.7630 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2691 0.8981 -0.7505 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3395 -0.9022 2.2920 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6038 0.8062 2.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0004 0.1044 2.8491 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5826 2.6239 1.2732 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8137 2.2288 -0.4409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8388 3.1483 0.5295 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0567 1.7682 1.6140 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9115 1.6052 -1.4049 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5287 -1.9931 -1.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5512 -0.9171 -2.2746 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2400 -0.4244 -1.8932 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5956 -0.2315 1.8274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1578 -1.8587 1.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6202 -0.9773 0.5940 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0051 0.0262 -1.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0463 -2.2622 0.8033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4972 -2.3499 -0.9265 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0599 -2.8303 -0.5501 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4866 -1.4596 -1.6871 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2351 -2.0088 1.8870 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4065 -2.3724 1.3330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0891 -0.8887 2.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0356 1.7445 -1.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9535 0.6934 -1.2583 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 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 1 21 30 1 0 13 31 1 0 31 4 1 0 31 7 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 1 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 8 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 12 51 1 0 12 52 1 0 12 53 1 0 13 54 1 1 14 55 1 0 14 56 1 0 15 57 1 0 15 58 1 0 16 59 1 6 18 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 21 67 1 6 23 68 1 0 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 24 73 1 0 25 74 1 6 26 75 1 0 26 76 1 0 27 77 1 0 27 78 1 0 29 79 1 0 29 80 1 0 29 81 1 0 30 82 1 0 31 83 1 6 M END

Standard InCHIKey	UBLNLUPLUKPSPP-QGTGJCAVSA-N
Standard InCHI	InChI=1S/C30H52O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h19-25,31H,9-18H2,1-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
SMILES	CC(C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	428.4	Volume:	493.444 ? Van der Waals volume.
Dense:	0.868	LogP:	7.319 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.268 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.714 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	25.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.447	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.63	Fsp³:	1.0
MCE-18:	99.9 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.915	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.598	Promiscuous compounds:	0.134

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.322	MDCK Permeability:	-5.026
Pgp-inhibitor:	0.82	Pgp-substrate:	0.15
PAMPA:	0.454 ? 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%):	0.47	30% Bioavailability (F30%):	0.139
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.942	MRP1:	0.96
Plasma Protein Binding (PPB):	97.824%	Volume Distribution (VD):	0.101
Fu:	2.616% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.971	BCRP inhibitor:	0.719
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.105	CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.601
CYP2D6-inhibitor:	0.437	CYP2D6-substrate:	0.027
CYP3A4-inhibitor:	0.97	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.86
HLM stability:	0.828 ? 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):

11.211

Half-life (T1/2):

0.206

ADMET: Toxicity

hERG Blockers:	0.115	hERG Blockers (10um):	0.305
Human Hepatotoxicity (H-HT):	0.592	Drug-induced Liver Injury (DILI):	0.326
AMES Toxicity:	0.414	Rat Oral Acute Toxicity:	0.365
Maximum Recommended Daily Dose:	0.585	Skin Sensitization:	0.962
Carcinogencity:	0.92	Eye Corrosion:	0.483
Eye Irritation:	0.846	Respiratory Toxicity:	0.914
Drug-induced Neurotoxicity:	0.102	Ototoxicity:	0.419
Hematotoxicity:	0.589	Drug-induced Nephrotoxicity:	0.763
Genotoxicity:	0.279	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.444	Hek293 Cytotoxicity:	0.513
BCF:	3.147 ? 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:	4.801 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.064 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.395 ? 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
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11627-001-0052-8]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO4892	Viburnum davidii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1584	Tolypothrix tjipanasensis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2161	Strychnos ledermannii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17549	Polemonium caeruleum	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO245	Euphorbia biglandulosa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13123	Balanophora harlandii	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO513	Agathosma scaberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2161	Strychnos ledermannii	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO513	Agathosma scaberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4892	Viburnum davidii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17549	Polemonium caeruleum	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1584	Tolypothrix tjipanasensis	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13123	Balanophora harlandii	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO245	Euphorbia biglandulosa	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

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 NPC57233 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	30430
0.1-0.2	16703
0.2-0.3	2188
0.3-0.4	377
0.4-0.5	90
0.5-0.6	43
0.6-0.7	10
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
0.7826	Intermediate Similarity	NPC142712
0.766	Intermediate Similarity	NPC480925
0.766	Intermediate Similarity	NPC48079
0.75	Intermediate Similarity	NPC192638
0.75	Intermediate Similarity	NPC25511
0.75	Intermediate Similarity	NPC600137
0.7347	Intermediate Similarity	NPC97534
0.7347	Intermediate Similarity	NPC195155
0.7059	Intermediate Similarity	NPC248830
0.7059	Intermediate Similarity	NPC212241
0.6863	Remote Similarity	NPC301226
0.6792	Remote Similarity	NPC269396
0.6667	Remote Similarity	NPC298168
0.6667	Remote Similarity	NPC143133
0.6538	Remote Similarity	NPC144075
0.6122	Remote Similarity	NPC232112
0.6111	Remote Similarity	NPC231256
0.6111	Remote Similarity	NPC178383
0.6	Remote Similarity	NPC5767
0.6	Remote Similarity	NPC475742
0.5893	Remote Similarity	NPC246956
0.5893	Remote Similarity	NPC74595
0.5893	Remote Similarity	NPC119355
0.5893	Remote Similarity	NPC264665
0.5714	Remote Similarity	NPC93662
0.569	Remote Similarity	NPC12774
0.5667	Remote Similarity	NPC483720
0.5636	Remote Similarity	NPC104387
0.5636	Remote Similarity	NPC202540
0.5593	Remote Similarity	NPC477578
0.5593	Remote Similarity	NPC477577
0.5556	Remote Similarity	NPC606606
0.55	Remote Similarity	NPC289486
0.5455	Remote Similarity	NPC472741
0.5455	Remote Similarity	NPC185536
0.5439	Remote Similarity	NPC211009
0.5439	Remote Similarity	NPC201725
0.5439	Remote Similarity	NPC602784
0.541	Remote Similarity	NPC481321
0.541	Remote Similarity	NPC607755
0.5357	Remote Similarity	NPC245869
0.5357	Remote Similarity	NPC91573
0.5357	Remote Similarity	NPC240235
0.5357	Remote Similarity	NPC14112
0.5263	Remote Similarity	NPC42853
0.5263	Remote Similarity	NPC58631
0.5263	Remote Similarity	NPC237460
0.5263	Remote Similarity	NPC285761
0.5263	Remote Similarity	NPC34930
0.5192	Remote Similarity	NPC11908
0.5179	Remote Similarity	NPC102708
0.5172	Remote Similarity	NPC296701
0.5172	Remote Similarity	NPC218616
0.5167	Remote Similarity	NPC472608
0.5167	Remote Similarity	NPC477508
0.5167	Remote Similarity	NPC603388
0.5091	Remote Similarity	NPC129829
0.5088	Remote Similarity	NPC78067
0.5088	Remote Similarity	NPC278091
0.5085	Remote Similarity	NPC91387
0.5085	Remote Similarity	NPC13554
0.5085	Remote Similarity	NPC231680
0.5085	Remote Similarity	NPC270306

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC57233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7956
0.1-0.2	1134
0.2-0.3	55
0.3-0.4	4
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