NPASS Compound

Natural Product: NPC296770

Natural Product ID	NPC296770
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VNOKAWVKCFUZGK-HOJYRBEBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5320337
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 81 85 0 0 0 0 0 0 0 0999 V2000 -6.1310 -0.9545 -1.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2231 -0.5110 0.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7670 -1.1133 1.3185 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8336 -0.9821 -0.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5828 -0.5965 -1.7138 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4663 0.3667 -1.9269 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2197 -0.1665 -1.2609 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7131 -1.2959 -2.1747 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1941 0.9538 -1.4369 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1828 0.5122 -1.1067 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0199 1.0802 -1.9789 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4549 0.8608 -1.9437 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2316 1.2539 -2.8554 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0338 0.1505 -0.7992 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4434 0.5751 -0.5021 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3392 -0.1672 -1.5043 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7007 2.0348 -0.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8606 0.1490 0.8838 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0309 -1.0192 1.3706 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5752 -0.6366 1.5298 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1059 0.2477 0.3696 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8269 1.6362 0.8362 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7713 -0.3622 -0.0888 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9206 -0.6853 1.0815 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4208 0.0485 1.0999 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3968 -0.6064 0.1352 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7965 -0.5368 0.6908 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8279 -1.6181 1.8009 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0980 0.7443 1.4037 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1506 1.6103 0.8598 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2363 0.9825 0.0831 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5177 1.3683 0.5454 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1851 -0.2654 0.8320 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0732 -1.4230 -0.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6497 -1.7479 -1.6944 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4664 -0.0974 -1.6959 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6232 -0.3908 2.1594 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8902 -1.1671 1.1998 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4437 -2.1280 1.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9101 -2.1135 -0.2902 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3639 -1.4876 -2.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4934 -0.1412 -2.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2475 0.3549 -3.0391 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6781 1.4078 -1.6954 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3863 -1.2538 -2.2858 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0731 -2.2470 -1.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1486 -1.2293 -3.1803 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4978 1.8899 -0.9451 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2716 1.2000 -2.5427 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6359 1.7336 -2.7512 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0590 -0.9430 -1.0853 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8798 -1.1374 -1.7864 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3908 0.4333 -2.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3535 -0.3216 -1.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5739 2.2369 -1.3679 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8703 2.6186 -1.0709 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0137 2.4929 0.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7509 1.0211 1.5498 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4027 -1.2708 2.3875 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1876 -1.8859 0.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -1.5876 1.5720 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4014 -0.0984 2.4766 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3534 1.5426 1.8584 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0647 2.1657 0.2288 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7379 2.2412 1.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0862 -1.3536 -0.5368 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4391 -0.3651 2.0107 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7192 -1.7692 1.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7787 -0.0120 2.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1919 1.0875 0.8888 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0951 -1.6996 0.1653 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4650 -1.3223 2.6321 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8029 -1.7705 2.2162 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1023 -2.6066 1.3562 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2899 0.6135 2.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1346 1.3396 1.4142 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6278 2.2022 1.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6906 2.4192 0.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2355 1.3184 -0.9967 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4575 1.4296 1.5414 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2799 -1.2361 1.0112 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 6 7 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 18 33 1 0 31 2 1 0 27 4 1 0 26 7 1 0 23 10 1 0 21 14 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 14 51 1 6 16 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 0 20 62 1 0 22 63 1 0 22 64 1 0 22 65 1 0 23 66 1 6 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 29 76 1 0 30 77 1 0 30 78 1 0 31 79 1 6 32 80 1 0 33 81 1 0 M END

Standard InCHIKey	VNOKAWVKCFUZGK-HOJYRBEBSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-26(2)21-10-13-28(5)17-18-16-20(31)25-27(3,4)24(33)11-14-29(25,6)19(18)8-9-22(28)30(21,7)15-12-23(26)32/h16,19,21-25,32-33H,8-15,17H2,1-7H3/t19-,21?,22?,23-,24?,25-,28-,29?,30-/m0/s1
SMILES	CC1(C)C2CC[C@@]3(C)CC4=CC(=O)[C@H]5C(C)(C)C(CCC5(C)[C@H]4CCC3[C@@]2(C)CC[C@@H]1O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	505.751 ? Van der Waals volume.
Dense:	0.902	LogP:	3.92 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.864 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.001 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	28.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.448	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.896	Fsp³:	0.9
MCE-18:	102.667 ? 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:	0.406	Fluc inhibitor:	0.019 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.276	Promiscuous compounds:	0.19

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.016	MDCK Permeability:	-4.79
Pgp-inhibitor:	0.062	Pgp-substrate:	0.49
PAMPA:	0.975 ? 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%):	0.244	30% Bioavailability (F30%):	0.035
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173	MRP1:	0.874
Plasma Protein Binding (PPB):	85.399%	Volume Distribution (VD):	-0.165
Fu:	11.887% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.176
BSEP inhibitor:	0.812

ADMET: Metabolism

CYP1A2-inhibitor:	0.095	CYP1A2-substrate:	0.717
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.095	CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.082	CYP2C8-inhibitor:	0.209
HLM stability:	0.993 ? 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):

13.123

Half-life (T1/2):

0.667

ADMET: Toxicity

hERG Blockers:	0.131	hERG Blockers (10um):	0.363
Human Hepatotoxicity (H-HT):	0.64	Drug-induced Liver Injury (DILI):	0.05
AMES Toxicity:	0.317	Rat Oral Acute Toxicity:	0.371
Maximum Recommended Daily Dose:	0.885	Skin Sensitization:	0.728
Carcinogencity:	0.653	Eye Corrosion:	0.0
Eye Irritation:	0.26	Respiratory Toxicity:	0.598
Drug-induced Neurotoxicity:	0.065	Ototoxicity:	0.732
Hematotoxicity:	0.224	Drug-induced Nephrotoxicity:	0.499
Genotoxicity:	0.103	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.528	Hek293 Cytotoxicity:	0.555
BCF:	2.065 ? 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:	4.921 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.503 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.804 ? 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
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 12877918]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245240]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[25442304]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24671	Lycopodium japonicum	Species	Lycopodiaceae	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 NPC296770 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	18222
0.1-0.2	25897
0.2-0.3	5162
0.3-0.4	488
0.4-0.5	77
0.5-0.6	7
0.6-0.7	5
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8302	Intermediate Similarity	NPC472802
0.6949	Remote Similarity	NPC89225
0.6885	Remote Similarity	NPC167193
0.6604	Remote Similarity	NPC472805
0.6604	Remote Similarity	NPC90979
0.625	Remote Similarity	NPC601949
0.5932	Remote Similarity	NPC609913
0.5846	Remote Similarity	NPC472806
0.5556	Remote Similarity	NPC599915
0.5323	Remote Similarity	NPC611107
0.5156	Remote Similarity	NPC602872
0.5082	Remote Similarity	NPC600728
0.5075	Remote Similarity	NPC295643

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC296770 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6795
0.1-0.2	2154
0.2-0.3	196
0.3-0.4	4
0.4-0.5	1
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