NPASS Compound

Natural Product: NPC602216

Natural Product ID	NPC602216
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QDQJWSSPAMZRIA-AIWMZPBQSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2367704
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 92 97 0 0 0 0 0 0 0 0999 V2000 0.3177 5.1814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1459 3.7548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8578 2.6401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3250 2.9520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3694 0.1624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2686 0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2668 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5863 -1.0950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0741 -0.9042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6567 0.4034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2353 1.7873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2668 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2668 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5658 -3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5658 -5.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8648 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8648 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3420 -7.2395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3062 -8.3886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6053 -9.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9043 -9.8886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7932 -9.7981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7932 -11.2981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3160 -10.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0169 -10.8086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3518 -8.9095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0528 -8.1595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2668 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2668 -7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -5.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5095 -4.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3313 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3313 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6304 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6304 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9294 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3313 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3671 2.6491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8802 4.0586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3574 4.3191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9160 5.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0482 6.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0124 7.5058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1009 7.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1126 6.4534 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9544 5.9764 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6771 4.5474 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5922 -2.1163 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5293 -2.3955 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5658 -0.7500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2038 -2.4620 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8171 0.3989 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1493 0.2547 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7231 1.9781 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0962 -5.9554 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0576 -5.2044 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5911 -5.2044 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8648 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3876 -7.2395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2704 -7.2395 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3553 -7.8396 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0192 -10.5194 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2033 -9.1386 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2276 -10.2367 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5953 -12.2009 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6534 -11.5202 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0169 -12.3086 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3876 -10.0586 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2463 -8.9095 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5453 -6.6595 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9867 -4.7291 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7700 -6.4667 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6142 -3.4932 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4131 -4.3361 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8293 -2.9215 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3155 -4.1320 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7121 -2.0861 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2955 2.6491 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1740 6.0246 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4322 4.5502 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3062 5.5398 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9766 8.6549 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0106 8.6029 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1614 6.5416 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2499 8.2851 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2840 8.5789 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1979 6.2980 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5192 2.1595 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 5 3 1 1 5 6 1 0 6 7 1 0 8 7 1 6 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 9 14 1 0 14 15 1 6 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 17 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 40 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 1 0 45 46 1 0 45 47 1 0 40 48 1 0 12 5 1 0 34 14 1 0 48 5 1 0 36 8 1 0 48 8 1 0 28 19 1 0 1 49 1 0 1 50 1 0 1 51 1 0 7 52 1 0 7 53 1 0 9 54 1 1 10 55 1 1 11 56 1 0 12 57 1 6 13 58 1 0 15 59 1 0 15 60 1 0 15 61 1 0 16 62 1 0 19 63 1 1 21 64 1 1 22 65 1 0 22 66 1 0 23 67 1 0 24 68 1 6 25 69 1 0 26 70 1 1 27 71 1 0 28 72 1 6 29 73 1 0 32 74 1 6 33 75 1 0 33 76 1 0 33 77 1 0 34 78 1 1 35 79 1 0 35 80 1 0 36 81 1 6 40 82 1 1 44 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 46 87 1 0 46 88 1 0 47 89 1 0 47 90 1 0 47 91 1 0 48 92 1 6 M END

Standard InCHIKey	QDQJWSSPAMZRIA-AIWMZPBQSA-N
Standard InCHI	InChI=1S/C32H44O16/c1-11(2)6-17(34)48-23-25-31-10-44-32(25,29(42)43-5)26(40)22(39)24(31)30(4)8-14(18(35)12(3)13(30)7-16(31)47-27(23)41)45-28-21(38)20(37)19(36)15(9-33)46-28/h8,11-13,15-16,19-26,28,33,36-40H,6-7,9-10H2,1-5H3/t12-,13-,15+,16+,19+,20-,21+,22+,23+,24+,25+,26-,28+,30-,31+,32+/m0/s1
SMILES	COC(=O)[C@]12OC[C@]34[C@H]([C@@H](O)[C@@H]1O)[C@@]1(C)C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(=O)[C@@H](C)[C@@H]1C[C@H]3OC(=O)[C@H](OC(=O)CC(C)C)[C@@H]24

Calculated Properties

Physi-Chem Properties

Molecular Weight:	684.26	Volume:	638.151 ? Van der Waals volume.
Dense:	1.072	LogP:	0.265 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.254 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.464 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	33.0
TPSA:	245.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.122	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.954	Fsp³:	0.812
MCE-18:	166.552 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.711	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.096	Promiscuous compounds:	0.231

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.798	MDCK Permeability:	-5.203
Pgp-inhibitor:	0.0	Pgp-substrate:	0.497
PAMPA:	0.995 ? 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):	0.014
20% Bioavailability (F20%):	0.009	30% Bioavailability (F30%):	0.663
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.654
Plasma Protein Binding (PPB):	65.295%	Volume Distribution (VD):	-0.243
Fu:	34.846% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.008

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.008	CYP3A4-substrate:	0.925
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.023 ? 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):

1.442

Half-life (T1/2):

3.665

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.017
Human Hepatotoxicity (H-HT):	0.761	Drug-induced Liver Injury (DILI):	0.971
AMES Toxicity:	0.963	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.07	Skin Sensitization:	1.0
Carcinogencity:	0.305	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.065	Ototoxicity:	0.983
Hematotoxicity:	0.461	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.961	RPMI-8226 Immunitoxicity:	0.363
A549 Cytotoxicity:	0.192	Hek293 Cytotoxicity:	0.301
BCF:	0.498 ? 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:	3.259 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.008 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.141 ? 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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14948	Brucea javanica	Species	Simaroubaceae	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

Activity Type	# Activity
EC50	1
IC50	1

Activity Type	# Activity
Cell line	1
Organism	1

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
NPT759	Cell line	H9	Homo sapiens	IC50	=	146000.0	nM	DOI[10.1016/0960-894X(96)00096-0]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	110000.0	nM	DOI[10.1016/0960-894X(96)00096-0]

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 NPC602216 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	18237
0.1-0.2	27902
0.2-0.3	3588
0.3-0.4	80
0.4-0.5	24
0.5-0.6	8
0.6-0.7	8
0.7-0.8	0
0.8-0.85	2
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC475636
0.8953	High Similarity	NPC54614
0.8929	High Similarity	NPC190065
0.8721	High Similarity	NPC141215
0.8621	High Similarity	NPC479019
0.8523	High Similarity	NPC295885
0.8427	Intermediate Similarity	NPC140045
0.8242	Intermediate Similarity	NPC471089
0.7865	Intermediate Similarity	NPC309096
0.7684	Intermediate Similarity	NPC102465
0.6875	Remote Similarity	NPC295220
0.6804	Remote Similarity	NPC480779
0.6667	Remote Similarity	NPC596
0.6535	Remote Similarity	NPC480778
0.6421	Remote Similarity	NPC87662
0.6263	Remote Similarity	NPC262813
0.6139	Remote Similarity	NPC480789
0.6019	Remote Similarity	NPC251998
0.5833	Remote Similarity	NPC480790
0.5652	Remote Similarity	NPC476008
0.5435	Remote Similarity	NPC485623
0.5376	Remote Similarity	NPC16081
0.5158	Remote Similarity	NPC146432
0.5158	Remote Similarity	NPC470778
0.5109	Remote Similarity	NPC213084
0.5106	Remote Similarity	NPC479018

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC602216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6854
0.1-0.2	2232
0.2-0.3	64
0.3-0.4	0
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