NPASS Compound

Natural Product: NPC312507

Natural Product ID	NPC312507
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PSKOYUFGDWKJBO-OCXIHFKWSA-N
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: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 97102 0 0 0 0 0 0 0 0999 V2000 -6.3736 2.5200 -2.0423 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5113 1.0403 -1.6322 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3867 0.4371 -2.7191 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2964 1.0315 -0.3630 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9594 -0.0578 0.5799 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4807 -0.2499 0.8279 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8379 0.7865 1.6528 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5181 1.3076 1.2704 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6440 0.4838 0.4135 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1232 1.3636 -0.7157 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3824 -0.6463 -0.2187 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7531 -1.7815 -0.5110 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3166 -2.0593 -0.2590 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6161 -0.8151 0.0985 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8491 -1.0008 0.4396 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1323 -1.7896 1.6570 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4604 -1.7268 -0.7498 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 -1.7995 -0.7195 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6795 -0.5968 -0.2590 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8956 0.4854 0.4129 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4750 0.8060 1.8032 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2387 1.7817 -0.3616 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4214 0.3803 0.3996 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8004 1.2495 1.4366 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6218 1.1005 1.7181 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3768 -0.0408 1.1187 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8921 -0.9399 2.2229 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4505 -0.1163 -1.3424 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8728 -0.1611 -1.3007 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3554 -0.6435 -0.2635 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6247 0.3372 -2.4207 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9122 0.3924 -2.4368 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8751 0.0333 -1.4375 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0793 -0.5709 -1.8673 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1208 -0.8567 -1.0362 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0466 -0.5600 0.3055 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9010 0.0288 0.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8431 0.3152 -0.0996 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0865 -0.8423 1.1603 O 0 0 0 0 0 1 0 0 0 0 0 0 -4.8449 -0.5276 -0.5061 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2104 0.3518 -1.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4451 -1.5667 1.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9975 -1.6048 2.7505 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8882 -2.7411 1.0247 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3331 3.0285 -1.8357 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1303 2.6208 -3.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6065 2.9922 -1.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3054 -0.6659 -2.7565 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4733 0.6588 -2.5073 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1932 0.9134 -3.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3866 0.9696 -0.5746 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1857 2.0044 0.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3705 -1.0345 0.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4178 0.1451 1.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8486 0.4393 2.7325 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5687 1.6526 1.6995 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9603 1.5589 2.2214 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6599 2.3359 0.8091 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6936 2.3440 -0.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0807 1.7316 -0.5345 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0830 0.8549 -1.6921 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3936 -2.5608 -0.9831 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2183 -2.8360 0.5368 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9465 -2.5534 -1.1845 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5854 -0.1865 -0.8341 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2503 -1.2207 2.5913 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4252 -2.6369 1.7223 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1409 -2.2830 1.5117 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0574 -2.7609 -0.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1663 -1.2207 -1.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2542 -2.0819 -1.7718 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2302 -2.7310 -0.1446 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4147 -0.9578 0.4985 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2706 0.0475 2.5459 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5931 0.7696 1.6303 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2788 1.8481 2.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8318 2.6437 0.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3551 1.8489 -0.2935 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9335 1.6924 -1.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0824 0.7845 -0.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0626 2.3138 1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4151 1.0913 2.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1517 2.0635 1.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7734 1.0732 2.8407 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1047 -1.2491 2.9351 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5752 -0.2997 2.8517 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3719 -1.8551 1.8878 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0322 0.6859 -3.3054 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3555 0.7893 -3.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1471 -0.8089 -2.9250 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0404 -1.3205 -1.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7986 0.2794 1.8167 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0003 0.8570 0.3327 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2506 -1.5569 -0.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0827 -0.2523 -2.5801 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4313 1.1312 -1.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5380 -3.6335 1.3801 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 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 11 40 1 0 40 41 1 0 6 42 1 1 42 43 2 0 42 44 1 0 41 2 1 0 40 6 1 0 26 9 1 0 38 33 1 0 26 14 1 0 23 15 1 0 1 45 1 0 1 46 1 0 1 47 1 0 3 48 1 0 3 49 1 0 3 50 1 0 4 51 1 0 4 52 1 0 5 53 1 0 5 54 1 0 7 55 1 0 7 56 1 0 8 57 1 0 8 58 1 0 10 59 1 0 10 60 1 0 10 61 1 0 12 62 1 0 13 63 1 0 13 64 1 0 14 65 1 6 16 66 1 0 16 67 1 0 16 68 1 0 17 69 1 0 17 70 1 0 18 71 1 0 18 72 1 0 19 73 1 1 21 74 1 0 21 75 1 0 21 76 1 0 22 77 1 0 22 78 1 0 22 79 1 0 23 80 1 6 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 27 85 1 0 27 86 1 0 27 87 1 0 31 88 1 0 32 89 1 0 34 90 1 0 35 91 1 0 37 92 1 0 38 93 1 0 40 94 1 6 41 95 1 0 41 96 1 0 44 97 1 0 M CHG 1 39 -1 M END

Standard InCHIKey	PSKOYUFGDWKJBO-OCXIHFKWSA-N
Standard InCHI	InChI=1S/C39H54O5/c1-34(2)20-22-39(33(42)43)23-21-37(6)27(28(39)24-34)13-14-30-36(5)18-17-31(35(3,4)29(36)16-19-38(30,37)7)44-32(41)15-10-25-8-11-26(40)12-9-25/h8-13,15,28-31,40H,14,16-24H2,1-7H3,(H,42,43)/p-1/b15-10-/t28-,29-,30+,31+,36-,37+,38+,39-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](C(C)(C)[C@@H]5CC[C@@]34C)OC(=O)/C=Cc3ccc(cc3)[O-])[C@@H]2C1)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	602.4	Volume:	657.257 ? Van der Waals volume.
Dense:	0.917	LogP:	4.987 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.063 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.847 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	35.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.204	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.75	Fsp³:	0.692
MCE-18:	162.273 ? 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:	0.99	Fluc inhibitor:	0.885 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.068 ? 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:	0.266	Promiscuous compounds:	0.065

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.508	MDCK Permeability:	-5.038
Pgp-inhibitor:	0.584	Pgp-substrate:	0.0
PAMPA:	0.998 ? 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%):	0.629	30% Bioavailability (F30%):	0.192
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.538
Plasma Protein Binding (PPB):	98.054%	Volume Distribution (VD):	-0.264
Fu:	1.403% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.978	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.444	CYP2C19-substrate:	0.332
CYP2C9-inhibitor:	0.043	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.487	CYP3A4-substrate:	0.237
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.985
HLM stability:	0.133 ? 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):

3.182

Half-life (T1/2):

1.026

ADMET: Toxicity

hERG Blockers:	0.11	hERG Blockers (10um):	0.164
Human Hepatotoxicity (H-HT):	0.774	Drug-induced Liver Injury (DILI):	0.346
AMES Toxicity:	0.145	Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.485	Skin Sensitization:	0.999
Carcinogencity:	0.317	Eye Corrosion:	0.035
Eye Irritation:	0.76	Respiratory Toxicity:	0.832
Drug-induced Neurotoxicity:	0.164	Ototoxicity:	0.393
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.927
Genotoxicity:	0.219	RPMI-8226 Immunitoxicity:	0.027
A549 Cytotoxicity:	0.753	Hek293 Cytotoxicity:	0.511
BCF:	1.519 ? 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:	4.85 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.199 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.718 ? 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
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	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 NPC312507 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	13563
0.1-0.2	32919
0.2-0.3	2694
0.3-0.4	420
0.4-0.5	167
0.5-0.6	73
0.6-0.7	11
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
0.8072	Intermediate Similarity	NPC173569
0.7865	Intermediate Similarity	NPC610795
0.7303	Intermediate Similarity	NPC22676
0.7273	Intermediate Similarity	NPC120840
0.7126	Intermediate Similarity	NPC485587
0.7	Intermediate Similarity	NPC171007
0.7	Intermediate Similarity	NPC190849
0.6774	Remote Similarity	NPC605663
0.6768	Remote Similarity	NPC53520
0.6596	Remote Similarity	NPC172311
0.6465	Remote Similarity	NPC601567
0.6465	Remote Similarity	NPC606631
0.6344	Remote Similarity	NPC477874
0.6211	Remote Similarity	NPC477873
0.6186	Remote Similarity	NPC132126
0.6047	Remote Similarity	NPC485588
0.6042	Remote Similarity	NPC488215
0.6	Remote Similarity	NPC296164
0.5979	Remote Similarity	NPC198621
0.5979	Remote Similarity	NPC216940
0.5833	Remote Similarity	NPC200752
0.5814	Remote Similarity	NPC488521
0.5765	Remote Similarity	NPC485589
0.5758	Remote Similarity	NPC488214
0.5758	Remote Similarity	NPC482052
0.5699	Remote Similarity	NPC283849
0.5698	Remote Similarity	NPC608622
0.5568	Remote Similarity	NPC96580
0.5567	Remote Similarity	NPC18982
0.5545	Remote Similarity	NPC304110
0.5545	Remote Similarity	NPC27518
0.5545	Remote Similarity	NPC611516
0.5532	Remote Similarity	NPC606107
0.5506	Remote Similarity	NPC485586
0.5464	Remote Similarity	NPC43353
0.5431	Remote Similarity	NPC488211
0.5417	Remote Similarity	NPC286347
0.5392	Remote Similarity	NPC25491
0.5376	Remote Similarity	NPC485585
0.5368	Remote Similarity	NPC485882
0.5366	Remote Similarity	NPC604575
0.5349	Remote Similarity	NPC158141
0.5333	Remote Similarity	NPC111466
0.5327	Remote Similarity	NPC118033
0.53	Remote Similarity	NPC475472
0.5294	Remote Similarity	NPC480946
0.5294	Remote Similarity	NPC130577
0.5294	Remote Similarity	NPC142415
0.5294	Remote Similarity	NPC102683
0.5288	Remote Similarity	NPC482051
0.5287	Remote Similarity	NPC298554
0.5253	Remote Similarity	NPC284807
0.5253	Remote Similarity	NPC473538
0.5234	Remote Similarity	NPC180550
0.5234	Remote Similarity	NPC35405
0.5233	Remote Similarity	NPC156981
0.5208	Remote Similarity	NPC28198
0.5208	Remote Similarity	NPC476123
0.5204	Remote Similarity	NPC100383
0.52	Remote Similarity	NPC191410
0.5196	Remote Similarity	NPC262970
0.5192	Remote Similarity	NPC479739
0.5192	Remote Similarity	NPC178093
0.5189	Remote Similarity	NPC469945
0.5185	Remote Similarity	NPC481234
0.5185	Remote Similarity	NPC479431
0.5152	Remote Similarity	NPC182249
0.5152	Remote Similarity	NPC473591
0.5152	Remote Similarity	NPC248287
0.5152	Remote Similarity	NPC234548
0.5149	Remote Similarity	NPC469447
0.5149	Remote Similarity	NPC475611
0.5146	Remote Similarity	NPC479744
0.5143	Remote Similarity	NPC6377
0.5143	Remote Similarity	NPC208381
0.5143	Remote Similarity	NPC324798
0.5143	Remote Similarity	NPC479742
0.5104	Remote Similarity	NPC204407
0.5098	Remote Similarity	NPC164194
0.5096	Remote Similarity	NPC56713
0.5096	Remote Similarity	NPC606782
0.5094	Remote Similarity	NPC479745
0.5081	Remote Similarity	NPC488212
0.5057	Remote Similarity	NPC270768
0.5057	Remote Similarity	NPC59263
0.5057	Remote Similarity	NPC210106
0.5054	Remote Similarity	NPC481362
0.505	Remote Similarity	NPC8102
0.505	Remote Similarity	NPC66894
0.5048	Remote Similarity	NPC114441
0.5048	Remote Similarity	NPC127056

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC312507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4022
0.1-0.2	5077
0.2-0.3	42
0.3-0.4	7
0.4-0.5	1
0.5-0.6	1
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
0.5096	Remote Similarity	NPD8166	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