NPASS Compound

Natural Product: NPC20976

Natural Product ID	NPC20976
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VUBCDVLKKVVOTB-ORVHFINVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325375
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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 103108 0 0 0 0 0 0 0 0999 V2000 -0.0333 -0.7904 3.0269 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1871 0.0006 2.4745 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5414 1.0228 3.5627 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3882 -0.8845 2.2874 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1080 -1.8254 1.1713 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8767 -1.1364 -0.1541 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0471 0.0915 -0.0696 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9185 0.7618 1.2375 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2850 0.0146 -0.7231 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9974 1.1285 -0.7991 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3239 1.2372 -1.4049 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0862 -0.0496 -1.5067 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4860 0.1456 -0.9529 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4476 -0.9419 -1.4396 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0229 1.4518 -1.5525 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5711 2.3902 -0.5417 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4080 1.6931 0.4993 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6802 0.6031 1.2228 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6411 -0.5041 1.5114 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2642 1.1852 2.5844 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4220 0.1948 0.5380 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8584 -1.0786 1.0550 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4199 -1.1788 0.5622 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3380 -1.2085 -0.9479 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8743 -2.5498 -1.3788 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8956 -1.1824 -1.3387 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6762 -1.0534 -2.8293 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1479 -2.4378 -0.9446 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3461 -2.1879 -1.0809 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7304 -2.0221 -2.4091 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6002 1.2527 -0.0970 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2472 -0.7868 -0.6580 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6318 -1.2666 -1.7472 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1053 0.0456 0.0316 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3742 0.3144 -0.5257 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4944 -0.1555 0.4060 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7792 -0.0138 -0.3613 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6868 0.9955 -1.4725 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6973 2.0799 -1.2300 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2972 3.2403 -0.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3699 4.2805 -0.4635 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5157 1.6767 -0.6646 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4451 0.3883 -2.7086 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8666 0.2447 0.4889 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2495 -1.4503 0.8317 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8828 -0.1884 3.1383 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3289 -1.0499 4.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1698 -1.7384 2.5390 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6308 1.5474 3.9129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3009 1.7331 3.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9589 0.4318 4.4057 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4425 -1.5171 3.2238 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2984 -0.2705 2.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0409 -2.4529 1.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3316 -2.5337 1.4518 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5844 0.8513 -0.7467 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5618 1.6812 1.2634 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1235 1.2000 1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5654 2.0617 -0.3852 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8796 2.0040 -0.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2227 1.7035 -2.4087 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2906 -0.2760 -2.5965 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8032 -1.5952 -0.6483 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0421 -1.4616 -2.3458 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4014 -0.4838 -1.8518 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8741 1.2425 -2.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2892 1.9468 -2.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2841 3.0883 -1.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8784 3.0447 -0.0219 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7432 2.5084 1.2083 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4550 -0.5411 0.7285 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1913 -1.4758 1.7134 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2124 -0.2344 2.4497 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9390 0.3788 3.2682 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5262 1.9751 2.4429 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2041 1.5982 3.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6601 0.9938 0.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7655 -0.9655 2.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4067 -1.9890 0.8562 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9170 -0.2846 0.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9759 -2.0742 1.0178 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1471 -3.3102 -0.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8691 -2.7112 -2.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8096 -2.8568 -0.8687 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4220 -2.0420 -3.3001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4943 -0.6444 -3.4023 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1996 -0.3955 -3.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3596 -2.8171 0.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3277 -3.1902 -1.7732 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8213 -3.1684 -0.7771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0647 -2.8325 -2.8335 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6255 1.4352 -1.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5127 -0.2155 -1.5033 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5263 0.5661 1.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9951 -1.0017 -0.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7102 1.4655 -1.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4436 2.5284 -2.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5877 2.9456 0.5771 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1831 3.5897 -1.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7388 4.1384 0.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2356 -0.0685 -3.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0580 -0.6046 0.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7120 -1.4034 1.6587 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 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 1 0 17 31 1 0 6 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 8 2 1 0 26 9 1 0 42 35 1 0 29 6 1 0 24 12 1 0 21 13 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 7 56 1 0 8 57 1 0 8 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 12 62 1 0 14 63 1 0 14 64 1 0 14 65 1 0 15 66 1 0 15 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 19 71 1 0 19 72 1 0 19 73 1 0 20 74 1 0 20 75 1 0 20 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 23 80 1 0 23 81 1 0 25 82 1 0 25 83 1 0 25 84 1 0 27 85 1 0 27 86 1 0 27 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 30 91 1 0 31 92 1 0 35 93 1 6 36 94 1 1 37 95 1 6 38 96 1 6 39 97 1 6 40 98 1 0 40 99 1 0 41100 1 0 43101 1 0 44102 1 0 45103 1 0 M END

Standard InCHIKey	VUBCDVLKKVVOTB-ORVHFINVSA-N
Standard InCHI	InChI=1S/C36H58O9/c1-31(2)14-15-36(30(43)45-29-28(42)27(41)26(40)21(18-37)44-29)20(16-31)19-8-9-23-33(5)12-11-24(38)32(3,4)22(33)10-13-34(23,6)35(19,7)17-25(36)39/h8,20-29,37-42H,9-18H2,1-7H3/t20?,21-,22?,23?,24?,25?,26-,27+,28-,29+,33+,34-,35?,36?/m1/s1
SMILES	CC1(C)CCC2(C(C1)C1=CCC3[C@@]4(C)CCC(C(C)(C)C4CC[C@@]3(C)C1(C)CC2O)O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.41	Volume:	653.712 ? Van der Waals volume.
Dense:	0.97	LogP:	3.401 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.682 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.954 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	156.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.202	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.349	Fsp³:	0.917
MCE-18:	130.783 ? 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:	0.62	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.024 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.139	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.754	MDCK Permeability:	-5.114
Pgp-inhibitor:	0.0	Pgp-substrate:	0.069
PAMPA:	0.999 ? 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):	0.052
20% Bioavailability (F20%):	0.413	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13	MRP1:	0.627
Plasma Protein Binding (PPB):	71.758%	Volume Distribution (VD):	-0.275
Fu:	18.827% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.273	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.107	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.6
HLM stability:	0.166 ? 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):

2.761

Half-life (T1/2):

2.778

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.058
Human Hepatotoxicity (H-HT):	0.689	Drug-induced Liver Injury (DILI):	0.236
AMES Toxicity:	0.49	Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.122	Skin Sensitization:	0.966
Carcinogencity:	0.326	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.99
Hematotoxicity:	0.142	Drug-induced Nephrotoxicity:	0.777
Genotoxicity:	0.187	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.247	Hek293 Cytotoxicity:	0.298
BCF:	1.845 ? 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:	4.513 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.182 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.342 ? 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
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26020634]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8229021]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26138	Rosmarinus officinalis	Species	Lamiaceae	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 NPC20976 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	19956
0.1-0.2	23378
0.2-0.3	4917
0.3-0.4	1054
0.4-0.5	398
0.5-0.6	125
0.6-0.7	19
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	Natural Product ID
0.7922	Intermediate Similarity	NPC167383
0.775	Intermediate Similarity	NPC48249
0.7529	Intermediate Similarity	NPC1046
0.7442	Intermediate Similarity	NPC475208
0.7363	Intermediate Similarity	NPC305267
0.726	Intermediate Similarity	NPC488519
0.7073	Intermediate Similarity	NPC237503
0.6907	Remote Similarity	NPC69811
0.6818	Remote Similarity	NPC238935
0.6771	Remote Similarity	NPC64715
0.6632	Remote Similarity	NPC164389
0.6585	Remote Similarity	NPC191763
0.6548	Remote Similarity	NPC46388
0.6436	Remote Similarity	NPC11242
0.6374	Remote Similarity	NPC29069
0.6321	Remote Similarity	NPC25663
0.6207	Remote Similarity	NPC306746
0.6203	Remote Similarity	NPC164349
0.6176	Remote Similarity	NPC104137
0.6176	Remote Similarity	NPC26626
0.6105	Remote Similarity	NPC480420
0.6087	Remote Similarity	NPC214484
0.6075	Remote Similarity	NPC283417
0.6075	Remote Similarity	NPC200049
0.6	Remote Similarity	NPC253807
0.6	Remote Similarity	NPC158662
0.5976	Remote Similarity	NPC488520
0.5963	Remote Similarity	NPC4749
0.5962	Remote Similarity	NPC815
0.5929	Remote Similarity	NPC476991
0.5909	Remote Similarity	NPC21691
0.5876	Remote Similarity	NPC39211
0.5867	Remote Similarity	NPC34177
0.5859	Remote Similarity	NPC104071
0.5843	Remote Similarity	NPC37739
0.5833	Remote Similarity	NPC475516
0.5833	Remote Similarity	NPC488522
0.5804	Remote Similarity	NPC475514
0.5794	Remote Similarity	NPC123522
0.5789	Remote Similarity	NPC48499
0.5778	Remote Similarity	NPC604133
0.5769	Remote Similarity	NPC246708
0.5714	Remote Similarity	NPC295371
0.5699	Remote Similarity	NPC209894
0.5698	Remote Similarity	NPC488524
0.5676	Remote Similarity	NPC85154
0.567	Remote Similarity	NPC235405
0.5667	Remote Similarity	NPC199457
0.5658	Remote Similarity	NPC311078
0.5658	Remote Similarity	NPC101475
0.5657	Remote Similarity	NPC469946
0.5652	Remote Similarity	NPC302543
0.5644	Remote Similarity	NPC473459
0.5618	Remote Similarity	NPC605954
0.5612	Remote Similarity	NPC249848
0.5612	Remote Similarity	NPC150400
0.5612	Remote Similarity	NPC107966
0.5604	Remote Similarity	NPC137917
0.5604	Remote Similarity	NPC310014
0.5604	Remote Similarity	NPC68419
0.5604	Remote Similarity	NPC269315
0.56	Remote Similarity	NPC223301
0.56	Remote Similarity	NPC171544
0.5584	Remote Similarity	NPC235341
0.5575	Remote Similarity	NPC473452
0.5575	Remote Similarity	NPC286457
0.5556	Remote Similarity	NPC473884
0.5556	Remote Similarity	NPC220160
0.5556	Remote Similarity	NPC157868
0.5526	Remote Similarity	NPC470876
0.549	Remote Similarity	NPC488526
0.5476	Remote Similarity	NPC294360
0.5467	Remote Similarity	NPC290598
0.5467	Remote Similarity	NPC30590
0.5446	Remote Similarity	NPC192791
0.5446	Remote Similarity	NPC242840
0.5446	Remote Similarity	NPC112352
0.5437	Remote Similarity	NPC235438
0.5435	Remote Similarity	NPC7870
0.5435	Remote Similarity	NPC75747
0.5429	Remote Similarity	NPC104372
0.5417	Remote Similarity	NPC90856
0.5392	Remote Similarity	NPC30735
0.5392	Remote Similarity	NPC117714
0.5392	Remote Similarity	NPC30289
0.5385	Remote Similarity	NPC222580
0.5385	Remote Similarity	NPC297263
0.5385	Remote Similarity	NPC190837
0.5376	Remote Similarity	NPC110139
0.5376	Remote Similarity	NPC108709
0.5347	Remote Similarity	NPC76497
0.534	Remote Similarity	NPC40775
0.534	Remote Similarity	NPC10607
0.534	Remote Similarity	NPC251768
0.534	Remote Similarity	NPC159309
0.534	Remote Similarity	NPC102439
0.534	Remote Similarity	NPC46665
0.534	Remote Similarity	NPC2370
0.534	Remote Similarity	NPC86222
0.5316	Remote Similarity	NPC470588
0.5294	Remote Similarity	NPC51564
0.5288	Remote Similarity	NPC475591
0.5288	Remote Similarity	NPC63159
0.5288	Remote Similarity	NPC236870
0.5287	Remote Similarity	NPC283343
0.5278	Remote Similarity	NPC31838
0.5254	Remote Similarity	NPC144644
0.5254	Remote Similarity	NPC37860
0.5254	Remote Similarity	NPC170407
0.5234	Remote Similarity	NPC301449
0.5234	Remote Similarity	NPC601290
0.5227	Remote Similarity	NPC473160
0.5217	Remote Similarity	NPC116794
0.5213	Remote Similarity	NPC271138
0.52	Remote Similarity	NPC139894
0.5192	Remote Similarity	NPC44716
0.5185	Remote Similarity	NPC80986
0.5167	Remote Similarity	NPC142151
0.5167	Remote Similarity	NPC267694
0.5164	Remote Similarity	NPC489209
0.5161	Remote Similarity	NPC65590
0.5161	Remote Similarity	NPC125923
0.5152	Remote Similarity	NPC179434
0.514	Remote Similarity	NPC281148
0.514	Remote Similarity	NPC114484
0.5138	Remote Similarity	NPC207738
0.5138	Remote Similarity	NPC481078
0.5138	Remote Similarity	NPC187290
0.5125	Remote Similarity	NPC159168
0.5104	Remote Similarity	NPC128925
0.5104	Remote Similarity	NPC256798
0.5102	Remote Similarity	NPC204458
0.5102	Remote Similarity	NPC189884
0.5102	Remote Similarity	NPC138334
0.5086	Remote Similarity	NPC473386
0.5082	Remote Similarity	NPC68767
0.5082	Remote Similarity	NPC293031
0.5081	Remote Similarity	NPC33012
0.5059	Remote Similarity	NPC49776
0.5059	Remote Similarity	NPC63118
0.5059	Remote Similarity	NPC474436
0.5053	Remote Similarity	NPC102914
0.5052	Remote Similarity	NPC607754
0.5049	Remote Similarity	NPC263756
0.5049	Remote Similarity	NPC213674
0.5046	Remote Similarity	NPC481030
0.5045	Remote Similarity	NPC213952
0.5041	Remote Similarity	NPC110385
0.5041	Remote Similarity	NPC153673
0.5041	Remote Similarity	NPC482010
0.5041	Remote Similarity	NPC51099

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC20976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7262
0.1-0.2	1808
0.2-0.3	75
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