NPASS Compound

Natural Product: NPC490125

Natural Product ID	NPC490125
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Capsicoside A1
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

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 96102 0 0 0 0 0 0 0 0999 V2000 -4.7842 1.6606 1.5283 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1681 1.2970 0.1486 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2922 0.4843 -0.6558 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1785 -0.7158 0.3154 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4032 -1.6118 -0.5700 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3221 -0.6368 -1.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1362 -0.8204 -0.2256 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3977 -2.0632 -0.6739 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9759 -2.1941 -0.0994 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7686 -0.9410 -0.3350 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1787 -1.1644 0.0883 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0231 0.0894 -0.0330 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2345 -0.1618 0.5434 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3341 -0.0461 -0.2609 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1161 0.9672 0.1915 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4089 1.0837 -0.1498 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2601 0.9358 1.1226 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6173 1.0668 0.8657 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9941 0.2418 -1.2163 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2591 -0.2094 -0.7899 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1794 -0.9725 -1.4916 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5706 -0.7712 -2.7469 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1394 -1.2882 -0.4380 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3920 -2.3533 -0.9396 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3219 1.1597 0.7974 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3519 0.7202 2.1186 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9175 1.4084 0.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0735 0.1671 0.4389 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9357 -0.1620 1.8946 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2459 0.3969 -0.2326 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0725 1.4865 0.4193 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1636 1.8391 -0.5571 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9562 0.7297 -1.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0591 1.0658 -2.6279 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5018 -0.9801 0.4925 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2462 0.1934 0.3318 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2594 0.4796 1.3340 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6542 0.3191 0.7119 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7845 -0.9156 -0.1145 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9832 -0.7123 -1.0502 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5498 -1.1062 -0.9449 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8339 0.0807 -0.9512 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9979 2.7648 1.6564 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7393 1.5333 1.8146 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3589 1.1362 2.3437 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6500 2.1337 -0.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9044 0.0312 -1.5023 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6308 -0.4170 1.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9496 -2.4278 0.0017 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0268 -1.9510 -1.4082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0718 -1.0451 -2.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4976 -1.0479 0.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3270 -2.0108 -1.7911 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9763 -2.9650 -0.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4875 -3.0145 -0.6107 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9168 -2.3822 0.9931 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7383 -0.6535 -1.3954 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2301 -1.5730 1.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6177 -1.9220 -0.5832 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0576 0.3579 -1.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9478 0.2568 -1.2806 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5656 2.1875 -0.4744 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1077 -0.0384 1.6173 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9284 1.7022 1.8719 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1347 0.5651 1.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1975 0.8283 -2.1600 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9364 0.2872 -1.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8648 -1.8386 -1.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1049 -0.1170 -3.2821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6651 -1.5559 0.4967 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7907 -1.9895 -1.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8577 2.1208 0.7595 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6531 1.4584 2.7331 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5190 2.2568 0.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9863 1.6590 -0.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0409 0.8044 2.4678 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6640 -0.9153 2.2541 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0663 -0.5466 2.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 0.6483 -1.2898 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4408 1.0777 1.3786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4972 2.4010 0.6252 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6144 2.4540 -1.3403 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8782 2.6078 -0.1344 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0579 0.8374 -3.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3395 2.1245 -2.7417 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8037 0.3659 -3.0270 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2708 1.4955 1.7702 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2228 -0.2579 2.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8040 1.2161 0.0608 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3983 0.3098 1.5477 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9978 -1.8113 0.5093 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8397 -0.3074 -0.4703 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2346 -1.6648 -1.5681 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6876 0.0323 -1.8152 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8502 -1.3619 -1.9822 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8932 -1.8864 -0.5013 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 7 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 1 0 16 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 12 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 4 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 36 2 1 0 42 36 1 0 33 3 1 0 33 6 1 0 30 7 1 0 28 10 1 0 23 14 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 3 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 6 51 1 0 7 52 1 0 8 53 1 0 8 54 1 0 9 55 1 0 9 56 1 0 10 57 1 0 11 58 1 0 11 59 1 0 12 60 1 0 14 61 1 0 16 62 1 0 17 63 1 0 17 64 1 0 18 65 1 0 19 66 1 0 20 67 1 0 21 68 1 0 22 69 1 0 23 70 1 0 24 71 1 0 25 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 31 80 1 0 31 81 1 0 32 82 1 0 32 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 37 87 1 0 37 88 1 0 38 89 1 0 38 90 1 0 39 91 1 0 40 92 1 0 40 93 1 0 40 94 1 0 41 95 1 0 41 96 1 0 M END

Standard InCHIKey	YTZASGUOZDZYSL-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C33H54O9/c1-16-7-10-33(39-15-16)17(2)26-24(42-33)12-21-19-6-5-18-11-23(40-30-29(38)28(37)27(36)25(14-34)41-30)22(35)13-32(18,4)20(19)8-9-31(21,26)3/h16-30,34-38H,5-15H2,1-4H3
SMILES	CC1C2C(CC3C4CCC5CC(OC6OC(CO)C(O)C(O)C6O)C(O)CC5(C)C4CCC23C)OC11CCC(C)CO1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.38	Volume:	598.541 ? Van der Waals volume.
Dense:	0.993	LogP:	2.767 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.396 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.375 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	36.0
TPSA:	138.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	5.0	Rings:	7.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.312	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.863	Fsp³:	1.0
MCE-18:	173.182 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.013	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.055 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.029 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.135	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.198	MDCK Permeability:	-4.943
Pgp-inhibitor:	0.0	Pgp-substrate:	0.035
PAMPA:	0.743 ? 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):	0.143
20% Bioavailability (F20%):	0.041	30% Bioavailability (F30%):	0.634
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.87	MRP1:	1.0
Plasma Protein Binding (PPB):	67.041%	Volume Distribution (VD):	-0.348
Fu:	27.675% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.426	BCRP inhibitor:	0.007
BSEP inhibitor:	0.868

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.981	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.965	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.026	CYP2C8-inhibitor:	0.016
HLM stability:	0.037 ? 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):

5.515

Half-life (T1/2):

2.572

ADMET: Toxicity

hERG Blockers:	0.234	hERG Blockers (10um):	0.737
Human Hepatotoxicity (H-HT):	0.624	Drug-induced Liver Injury (DILI):	0.2
AMES Toxicity:	0.273	Rat Oral Acute Toxicity:	0.234
Maximum Recommended Daily Dose:	0.672	Skin Sensitization:	0.04
Carcinogencity:	0.232	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.127
Drug-induced Neurotoxicity:	0.506	Ototoxicity:	0.994
Hematotoxicity:	0.024	Drug-induced Nephrotoxicity:	0.024
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.096	Hek293 Cytotoxicity:	0.703
BCF:	1.791 ? 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:	4.267 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.836 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.95 ? 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
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12932131]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20460582]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[25172746]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8910532]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16501	Capsicum annuum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16501	Capsicum annuum	Species	Solanaceae	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
NPO16501	Capsicum annuum	Raw	Root	53	53	53	mg/100g	Database [DUKE]

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 NPC490125 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	25234
0.1-0.2	21189
0.2-0.3	2868
0.3-0.4	375
0.4-0.5	81
0.5-0.6	64
0.6-0.7	30
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8684	High Similarity	NPC294686
0.8228	Intermediate Similarity	NPC222731
0.7857	Intermediate Similarity	NPC195297
0.7586	Intermediate Similarity	NPC473601
0.7381	Intermediate Similarity	NPC54619
0.7283	Intermediate Similarity	NPC115165
0.7195	Intermediate Similarity	NPC297348
0.7195	Intermediate Similarity	NPC325828
0.7195	Intermediate Similarity	NPC249204
0.7195	Intermediate Similarity	NPC48339
0.7195	Intermediate Similarity	NPC141769
0.7195	Intermediate Similarity	NPC477547
0.7125	Intermediate Similarity	NPC24960
0.7108	Intermediate Similarity	NPC234352
0.6907	Remote Similarity	NPC83137
0.686	Remote Similarity	NPC206003
0.686	Remote Similarity	NPC121453
0.686	Remote Similarity	NPC473610
0.6824	Remote Similarity	NPC477451
0.6782	Remote Similarity	NPC211354
0.6782	Remote Similarity	NPC107188
0.675	Remote Similarity	NPC277715
0.6747	Remote Similarity	NPC485594
0.6629	Remote Similarity	NPC107962
0.6556	Remote Similarity	NPC6295
0.6531	Remote Similarity	NPC232611
0.6526	Remote Similarity	NPC151134
0.6471	Remote Similarity	NPC181845
0.6413	Remote Similarity	NPC160426
0.64	Remote Similarity	NPC470862
0.6386	Remote Similarity	NPC473774
0.6386	Remote Similarity	NPC481419
0.6386	Remote Similarity	NPC481417
0.6344	Remote Similarity	NPC475351
0.6263	Remote Similarity	NPC473518
0.6222	Remote Similarity	NPC19400
0.6207	Remote Similarity	NPC177834
0.618	Remote Similarity	NPC250393
0.6081	Remote Similarity	NPC227260
0.6024	Remote Similarity	NPC144790
0.6024	Remote Similarity	NPC149400
0.602	Remote Similarity	NPC128572
0.6	Remote Similarity	NPC481420
0.6	Remote Similarity	NPC481421
0.596	Remote Similarity	NPC97700
0.596	Remote Similarity	NPC184617
0.596	Remote Similarity	NPC30856
0.5867	Remote Similarity	NPC248944
0.5867	Remote Similarity	NPC7479
0.5867	Remote Similarity	NPC257296
0.5851	Remote Similarity	NPC125324
0.5729	Remote Similarity	NPC113044
0.5729	Remote Similarity	NPC283829
0.5729	Remote Similarity	NPC161676
0.5714	Remote Similarity	NPC475643
0.5701	Remote Similarity	NPC470867
0.5684	Remote Similarity	NPC485595
0.5652	Remote Similarity	NPC481190
0.5632	Remote Similarity	NPC481418
0.5603	Remote Similarity	NPC330026
0.56	Remote Similarity	NPC300557
0.5567	Remote Similarity	NPC14704
0.5566	Remote Similarity	NPC132080
0.5545	Remote Similarity	NPC480555
0.5545	Remote Similarity	NPC150372
0.5521	Remote Similarity	NPC470432
0.5521	Remote Similarity	NPC230507
0.5514	Remote Similarity	NPC31896
0.55	Remote Similarity	NPC92890
0.55	Remote Similarity	NPC477809
0.5481	Remote Similarity	NPC475625
0.5464	Remote Similarity	NPC141433
0.5446	Remote Similarity	NPC471464
0.5446	Remote Similarity	NPC51172
0.5446	Remote Similarity	NPC49032
0.5435	Remote Similarity	NPC131693
0.5435	Remote Similarity	NPC475436
0.54	Remote Similarity	NPC602423
0.5385	Remote Similarity	NPC481424
0.5385	Remote Similarity	NPC481422
0.5368	Remote Similarity	NPC306131
0.5368	Remote Similarity	NPC200802
0.5333	Remote Similarity	NPC32361
0.5333	Remote Similarity	NPC116756
0.5312	Remote Similarity	NPC264101
0.5288	Remote Similarity	NPC475319
0.5287	Remote Similarity	NPC88962
0.5283	Remote Similarity	NPC232037
0.5248	Remote Similarity	NPC470433
0.5248	Remote Similarity	NPC46190
0.5248	Remote Similarity	NPC171073
0.5234	Remote Similarity	NPC470864
0.519	Remote Similarity	NPC273290
0.519	Remote Similarity	NPC296734
0.519	Remote Similarity	NPC232044
0.5175	Remote Similarity	NPC210569
0.5158	Remote Similarity	NPC473616
0.5152	Remote Similarity	NPC70204
0.5146	Remote Similarity	NPC6806
0.5143	Remote Similarity	NPC51520
0.5143	Remote Similarity	NPC303069
0.5138	Remote Similarity	NPC480553
0.5128	Remote Similarity	NPC24556
0.5122	Remote Similarity	NPC329820
0.5102	Remote Similarity	NPC215408
0.5054	Remote Similarity	NPC481425
0.5054	Remote Similarity	NPC481426
0.5047	Remote Similarity	NPC470861

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC490125 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7440
0.1-0.2	1615
0.2-0.3	85
0.3-0.4	6
0.4-0.5	0
0.5-0.6	2
0.6-0.7	1
0.7-0.8	1
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
0.7195	Intermediate Similarity	NPD8171	Phase 2
0.6196	Remote Similarity	NPD8170	Phase 2
0.5867	Remote Similarity	NPD6928	Phase 2
0.5169	Remote Similarity	NPD7991	Discontinued

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