NPASS Compound

Natural Product: NPC479002

Natural Product ID	NPC479002
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HNSPETHWRWNYOS-XVCKLLAOSA-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]

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 98101 0 0 0 0 0 0 0 0999 V2000 12.2810 0.5050 0.3986 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1896 1.5320 0.5284 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0298 1.1859 -0.3858 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4532 -0.1662 -0.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9404 -0.1930 1.3952 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3728 -1.5430 1.7106 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2242 -1.9564 0.8586 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0140 -1.0943 0.9170 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3929 -1.0013 2.2917 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0924 -0.2871 2.2604 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1588 -0.7144 1.4663 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8363 -0.0901 1.3509 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8927 -0.5161 0.5514 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4261 0.0874 0.4211 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7369 1.0797 1.0919 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3463 -0.4288 -0.4429 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6354 0.0165 -0.6876 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6940 -0.8860 -0.0950 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1619 -1.2339 1.3082 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8903 -0.0008 0.1511 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3047 0.8098 -1.0242 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0207 2.0176 -0.4452 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8424 2.1170 0.5931 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3296 1.0816 1.5258 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3129 -0.2168 0.8371 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9283 -0.7687 0.8458 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1327 -2.1677 0.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3295 -2.5090 0.9616 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9747 -3.8663 0.8431 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9613 -1.3487 1.5988 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7911 -1.2753 2.5034 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9658 -0.2391 -0.3826 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3817 3.4862 0.8998 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8838 4.4008 -0.0084 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2779 1.2151 -1.9842 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8933 0.1782 -2.9986 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5101 -1.1639 -3.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7365 0.8118 -4.3966 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9538 0.6317 -1.9865 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8640 1.3904 -2.4982 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6434 0.8879 -2.8580 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3898 -0.3374 -2.7732 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4693 1.7509 -3.3741 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3960 0.9520 1.0921 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2887 -0.3477 3.1278 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2964 0.1613 0.3949 O 0 0 0 0 0 0 0 0 0 0 0 0 13.2761 0.9271 0.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0495 -0.3719 1.0541 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2732 0.1090 -0.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8839 1.6599 1.5789 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6022 2.5150 0.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4156 1.1321 -1.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2370 1.9531 -0.2869 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6919 -0.4296 -0.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3125 -0.8898 -0.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8415 -0.0266 2.0471 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2678 0.6509 1.5436 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2027 -2.2819 1.5161 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1893 -1.6305 2.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9197 -2.9961 1.1845 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5560 -2.0087 -0.1981 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2544 -1.5374 0.2331 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1924 -2.0020 2.7234 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8826 0.5805 2.8729 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3192 -1.5794 0.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6440 0.7724 1.9687 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1731 -1.4024 -0.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7012 0.9228 0.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8589 -1.8247 -0.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9779 -0.3203 1.8749 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8051 -1.9716 1.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1827 -1.7556 1.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1226 0.3283 -1.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8288 2.9528 -0.9667 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3744 1.3302 1.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7400 1.0263 2.4454 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6483 -0.7910 1.9532 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5049 -2.8822 -0.0195 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9718 -3.8542 1.3044 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3535 -4.5801 1.4614 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0252 -4.2140 -0.1935 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8808 -0.6077 -0.3406 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0842 3.7932 1.9320 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4884 3.4928 0.7964 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1299 4.9339 0.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3214 2.3076 -2.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9268 -1.4095 -4.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7291 -1.9729 -2.9492 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3283 -1.3834 -2.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3358 0.1031 -5.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7997 1.0228 -4.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2434 1.7805 -4.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2508 2.8216 -3.2431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5990 1.5065 -4.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3917 1.4240 -2.8629 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3624 1.8531 0.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0951 0.6052 3.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9871 0.2719 -0.5285 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 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 28 30 1 0 30 31 2 0 25 32 1 6 23 33 1 0 33 34 1 0 21 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 36 39 1 0 39 40 1 6 40 41 1 0 41 42 2 0 41 43 1 0 20 44 1 1 9 45 1 0 8 46 1 0 39 17 1 0 26 20 1 0 39 35 1 0 30 25 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 2 51 1 0 3 52 1 0 3 53 1 0 4 54 1 0 4 55 1 0 5 56 1 0 5 57 1 0 6 58 1 0 6 59 1 0 7 60 1 0 7 61 1 0 8 62 1 6 9 63 1 1 10 64 1 0 11 65 1 0 12 66 1 0 13 67 1 0 17 68 1 1 18 69 1 6 19 70 1 0 19 71 1 0 19 72 1 0 21 73 1 6 22 74 1 0 24 75 1 0 24 76 1 0 26 77 1 1 27 78 1 0 29 79 1 0 29 80 1 0 29 81 1 0 32 82 1 0 33 83 1 0 33 84 1 0 34 85 1 0 35 86 1 6 37 87 1 0 37 88 1 0 37 89 1 0 38 90 1 0 38 91 1 0 38 92 1 0 43 93 1 0 43 94 1 0 43 95 1 0 44 96 1 0 45 97 1 0 46 98 1 0 M END

Standard InCHIKey	HNSPETHWRWNYOS-XVCKLLAOSA-N
Standard InCHI	InChI=1S/C36H52O10/c1-7-8-9-10-11-14-26(39)27(40)15-12-13-16-29(41)45-32-22(3)35(44)25(30-33(5,6)36(30,32)46-23(4)38)18-24(20-37)19-34(43)28(35)17-21(2)31(34)42/h12-13,15-18,22,25-28,30,32,37,39-40,43-44H,7-11,14,19-20H2,1-6H3/b15-12+,16-13+/t22-,25+,26+,27+,28-,30-,32-,34-,35-,36-/m1/s1
SMILES	CCCCCCC[C@@H]([C@H](/C=C/C=C/C(=O)O[C@@H]1[C@@H](C)[C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C)C3=O)O)CO)[C@@H]2C(C)(C)[C@]12OC(=O)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	644.36	Volume:	666.433 ? Van der Waals volume.
Dense:	0.967	LogP:	3.149 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.37 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.434 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	23.0
TPSA:	170.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.066	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.501	Fsp³:	0.694
MCE-18:	83.803 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.627	Fluc inhibitor:	0.022 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.029 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.195	Promiscuous compounds:	0.528

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.255	MDCK Permeability:	-4.98
Pgp-inhibitor:	0.385	Pgp-substrate:	0.996
PAMPA:	0.986 ? 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):	0.83
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.067
Plasma Protein Binding (PPB):	92.403%	Volume Distribution (VD):	0.275
Fu:	8.797% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.941 ? 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):

3.278

Half-life (T1/2):

1.543

ADMET: Toxicity

hERG Blockers:	0.068	hERG Blockers (10um):	0.409
Human Hepatotoxicity (H-HT):	0.719	Drug-induced Liver Injury (DILI):	0.414
AMES Toxicity:	0.447	Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	0.739	Skin Sensitization:	0.995
Carcinogencity:	0.286	Eye Corrosion:	0.001
Eye Irritation:	0.406	Respiratory Toxicity:	0.897
Drug-induced Neurotoxicity:	0.066	Ototoxicity:	0.811
Hematotoxicity:	0.537	Drug-induced Nephrotoxicity:	0.893
Genotoxicity:	0.126	RPMI-8226 Immunitoxicity:	0.169
A549 Cytotoxicity:	0.474	Hek293 Cytotoxicity:	0.338
BCF:	0.578 ? 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:	3.69 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.597 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.585 ? 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
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28445049]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	Agarwood	n.a.	n.a.	PMID[29083898]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30672698]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7320738]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1692	Aquilaria malaccensis	Species	Thymelaeaceae	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
IC50	3
Activity	2

Activity Type	# Activity
Cell line	5

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
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[28445049]
NPT2740	Cell line	Neutrophils	n.a.	Activity	=	9.2	%	PMID[28445049]
NPT2740	Cell line	Neutrophils	n.a.	Activity	=	107.1	%	PMID[28445049]

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 NPC479002 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	16189
0.1-0.2	31766
0.2-0.3	1716
0.3-0.4	78
0.4-0.5	54
0.5-0.6	32
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC479001
0.7692	Intermediate Similarity	NPC484333
0.7595	Intermediate Similarity	NPC145238
0.7564	Intermediate Similarity	NPC478999
0.7229	Intermediate Similarity	NPC482199
0.7229	Intermediate Similarity	NPC482197
0.7179	Intermediate Similarity	NPC5991
0.7179	Intermediate Similarity	NPC196500
0.7179	Intermediate Similarity	NPC471108
0.7179	Intermediate Similarity	NPC5989
0.7059	Intermediate Similarity	NPC482198
0.7051	Intermediate Similarity	NPC275696
0.7051	Intermediate Similarity	NPC255081
0.6538	Remote Similarity	NPC171905
0.6538	Remote Similarity	NPC472397
0.6506	Remote Similarity	NPC22628
0.6506	Remote Similarity	NPC600005
0.6375	Remote Similarity	NPC472758
0.619	Remote Similarity	NPC243902
0.6173	Remote Similarity	NPC157252
0.6098	Remote Similarity	NPC471125
0.6024	Remote Similarity	NPC145182
0.5882	Remote Similarity	NPC471128
0.5882	Remote Similarity	NPC471126
0.587	Remote Similarity	NPC185876
0.587	Remote Similarity	NPC19336
0.5652	Remote Similarity	NPC138641
0.5652	Remote Similarity	NPC611243
0.5581	Remote Similarity	NPC488610
0.5568	Remote Similarity	NPC236918
0.5568	Remote Similarity	NPC156745
0.5517	Remote Similarity	NPC608501
0.5474	Remote Similarity	NPC601392
0.5444	Remote Similarity	NPC472759
0.5417	Remote Similarity	NPC601559
0.5361	Remote Similarity	NPC283875
0.5326	Remote Similarity	NPC472760
0.5275	Remote Similarity	NPC609983
0.5269	Remote Similarity	NPC472398
0.5269	Remote Similarity	NPC482219
0.5269	Remote Similarity	NPC600915
0.5222	Remote Similarity	NPC488611
0.5161	Remote Similarity	NPC484334
0.5155	Remote Similarity	NPC601964
0.5116	Remote Similarity	NPC485736
0.5116	Remote Similarity	NPC277477
0.5116	Remote Similarity	NPC479003
0.5116	Remote Similarity	NPC485735
0.5114	Remote Similarity	NPC485737
0.5109	Remote Similarity	NPC482221
0.5106	Remote Similarity	NPC482200
0.5104	Remote Similarity	NPC180640
0.5056	Remote Similarity	NPC19464
0.5054	Remote Similarity	NPC482220

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6407
0.1-0.2	2711
0.2-0.3	32
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