NPASS Compound

Natural Product: NPC125077

Natural Product ID	NPC125077
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Boivinide D
IUPAC Name	(3S,5S,8R,9S,10R,13R,14S,17R)-14-hydroxy-3-[(2R,4S,5R,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carbaldehyde
Synonyms	boivinide D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL249844
PubChem CID	24180057
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 100106 0 0 0 0 0 0 0 0999 V2000 4.4519 1.0021 1.2539 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4732 -0.4234 1.7175 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3371 -1.3170 0.8108 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4425 -2.2478 0.0366 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2465 -1.4231 -0.4368 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4413 -1.0716 0.7867 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2295 -0.9731 1.9271 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7595 0.1091 0.6442 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3754 -0.0040 0.7132 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2435 0.9419 1.6861 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7236 0.7557 1.7279 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3905 0.8465 0.3735 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4842 2.2833 0.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0705 3.1457 0.7861 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6201 0.0599 -0.6758 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2095 0.2651 -2.0312 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6738 -0.0400 -2.0798 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4335 0.4401 -0.8880 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7537 0.1903 0.4151 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6375 0.6747 1.5272 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8369 1.4382 1.0278 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6757 0.6759 0.0272 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4897 1.6866 -0.7445 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5995 -0.2950 0.6822 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9690 -1.6749 0.4953 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9576 -1.5464 -0.6031 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8458 -0.1091 -0.9392 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2811 0.0789 -2.2609 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9767 -0.3350 0.1521 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0401 -0.0648 0.8896 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2167 -0.1984 0.0569 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4387 -0.0127 0.4249 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8110 -0.5590 -1.2020 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4257 -0.6851 -1.2176 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1546 0.3947 -0.6711 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9375 -3.2743 0.8340 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9680 -0.4634 -0.0603 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3448 -0.4542 0.0092 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9178 -0.9051 -1.3131 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4314 -0.8261 -1.3475 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8589 0.5196 -0.8417 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2009 0.6935 0.5327 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7904 1.9459 1.1477 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1384 1.7834 1.3843 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8450 0.8264 0.2809 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2536 0.5153 -0.7188 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8612 -1.0229 -2.6431 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5562 -2.2116 -1.6202 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1889 1.6466 1.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7335 1.1363 0.1906 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4748 1.5067 1.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9879 -0.4253 2.7059 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0940 -1.8588 1.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9994 -2.6820 -0.7986 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5519 -0.5543 -1.0325 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6572 -2.1209 -1.0965 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6889 -1.8948 0.9251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0687 -1.0436 0.8770 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0149 1.9772 1.3441 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1367 0.8338 2.7191 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1256 1.6154 2.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9507 -0.1924 2.2565 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8959 2.6699 -0.9074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7246 -1.0116 -0.4074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9719 1.2625 -2.4675 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7063 -0.4724 -2.7246 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0931 0.4596 -2.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8657 -1.1369 -2.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5647 1.5527 -0.9845 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5325 -0.9079 0.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1364 1.3271 2.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0230 -0.1983 2.0977 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5045 2.3921 0.6119 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4851 1.6562 1.9000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3248 1.6245 -1.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1412 2.7224 -0.4564 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5564 1.6703 -0.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6302 -0.1220 1.7921 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5625 -2.0706 1.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7519 -2.4036 0.1432 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2425 -2.1536 -1.5079 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0261 -2.0238 -0.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2584 -0.7820 -2.7317 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0508 0.2137 1.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1484 -1.7579 -1.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9903 -0.0559 -2.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3512 -0.2532 -1.3870 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0107 1.4668 -0.8265 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1241 -3.1284 1.7941 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6918 -1.1802 0.7837 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5634 -0.2120 -2.1305 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9001 -1.5979 -0.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5102 1.3370 -1.4904 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4267 -0.1955 1.1254 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6340 2.7816 0.4484 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2477 2.1628 2.0845 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3235 1.6949 2.3551 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5618 1.4210 -0.9394 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1958 -1.5845 -3.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2752 -2.2458 -2.5550 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 13 14 2 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 24 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 1 0 15 35 1 0 4 36 1 0 3 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 40 47 1 0 39 48 1 0 7 2 1 0 35 9 1 0 45 38 1 0 19 12 1 0 27 22 1 0 34 29 1 0 27 18 1 0 1 49 1 0 1 50 1 0 1 51 1 0 2 52 1 1 3 53 1 1 4 54 1 6 5 55 1 0 5 56 1 0 6 57 1 1 9 58 1 1 10 59 1 0 10 60 1 0 11 61 1 0 11 62 1 0 13 63 1 0 15 64 1 1 16 65 1 0 16 66 1 0 17 67 1 0 17 68 1 0 18 69 1 6 19 70 1 1 20 71 1 0 20 72 1 0 21 73 1 0 21 74 1 0 23 75 1 0 23 76 1 0 23 77 1 0 24 78 1 1 25 79 1 0 25 80 1 0 26 81 1 0 26 82 1 0 28 83 1 0 30 84 1 0 34 85 1 0 34 86 1 0 35 87 1 0 35 88 1 0 36 89 1 0 38 90 1 1 39 91 1 6 40 92 1 1 41 93 1 6 42 94 1 1 43 95 1 0 43 96 1 0 44 97 1 0 46 98 1 0 47 99 1 0 48100 1 0 M END

Standard InCHIKey	DNLXAKKKWMFLON-WPXBXLIQSA-N
Standard InCHI	InChI=1S/C35H52O13/c1-17-31(48-32-30(42)29(41)28(40)25(14-36)47-32)24(38)13-27(45-17)46-20-5-9-34(16-37)19(12-20)3-4-23-22(34)6-8-33(2)21(7-10-35(23,33)43)18-11-26(39)44-15-18/h11,16-17,19-25,27-32,36,38,40-43H,3-10,12-15H2,1-2H3/t17-,19+,20+,21-,22+,23-,24+,25-,27+,28-,29+,30-,31+,32+,33-,34-,35+/m1/s1
SMILES	C[C@@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]1CC[C@@]2(C=O)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1)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:	680.34	Volume:	660.384 ? Van der Waals volume.
Dense:	1.03	LogP:	0.534 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.129 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.523 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	39.0
TPSA:	201.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	6.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.123	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.699	Fsp³:	0.886
MCE-18:	131.03 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.789	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.152	Promiscuous compounds:	0.159

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.28	MDCK Permeability:	-5.222
Pgp-inhibitor:	0.002	Pgp-substrate:	0.611
PAMPA:	0.951 ? 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):	0.001
20% Bioavailability (F20%):	0.089	30% Bioavailability (F30%):	0.702
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.023
Plasma Protein Binding (PPB):	54.285%	Volume Distribution (VD):	-0.427
Fu:	47.067% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.07
BSEP inhibitor:	0.943

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.9	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.003 ? 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):

1.008

Half-life (T1/2):

4.093

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.304
Human Hepatotoxicity (H-HT):	0.705	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.95
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.708	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.831
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.978
Hematotoxicity:	0.818	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.882
A549 Cytotoxicity:	0.734	Hek293 Cytotoxicity:	0.979
BCF:	0.525 ? 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:	3.281 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.927 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.997 ? 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
NPO33407	roupellina boivinii	Species	n.a.	n.a.	n.a.	Madagascar rainforest	n.a.	PMID[17988099]

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	1

Activity Type	# Activity
Cell line	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
NPT179	Cell line	A2780	Homo sapiens	IC50	=	290.0	nM	PMID[23822611]

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 NPC125077 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	15410
0.1-0.2	29574
0.2-0.3	4141
0.3-0.4	513
0.4-0.5	67
0.5-0.6	78
0.6-0.7	46
0.7-0.8	1
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8588	High Similarity	NPC188234
0.8519	High Similarity	NPC480914
0.8202	Intermediate Similarity	NPC329986
0.8202	Intermediate Similarity	NPC140092
0.8043	Intermediate Similarity	NPC475590
0.7889	Intermediate Similarity	NPC232785
0.7889	Intermediate Similarity	NPC486139
0.7872	Intermediate Similarity	NPC120390
0.7753	Intermediate Similarity	NPC475556
0.7753	Intermediate Similarity	NPC311706
0.7684	Intermediate Similarity	NPC74259
0.7582	Intermediate Similarity	NPC208193
0.7529	Intermediate Similarity	NPC469750
0.7527	Intermediate Similarity	NPC486138
0.7527	Intermediate Similarity	NPC276838
0.7444	Intermediate Similarity	NPC236973
0.7444	Intermediate Similarity	NPC32177
0.7444	Intermediate Similarity	NPC469756
0.7444	Intermediate Similarity	NPC275901
0.7326	Intermediate Similarity	NPC5311
0.7326	Intermediate Similarity	NPC77299
0.7326	Intermediate Similarity	NPC480906
0.7111	Intermediate Similarity	NPC72260
0.7071	Intermediate Similarity	NPC329675
0.7	Intermediate Similarity	NPC486150
0.6923	Remote Similarity	NPC480907
0.6907	Remote Similarity	NPC475219
0.6842	Remote Similarity	NPC486143
0.6842	Remote Similarity	NPC486135
0.6842	Remote Similarity	NPC486142
0.6842	Remote Similarity	NPC486137
0.6842	Remote Similarity	NPC486149
0.6809	Remote Similarity	NPC32793
0.6809	Remote Similarity	NPC116075
0.6774	Remote Similarity	NPC30483
0.6774	Remote Similarity	NPC470897
0.6733	Remote Similarity	NPC117445
0.6733	Remote Similarity	NPC308262
0.6702	Remote Similarity	NPC292467
0.6667	Remote Similarity	NPC76572
0.6667	Remote Similarity	NPC193382
0.6634	Remote Similarity	NPC475419
0.6632	Remote Similarity	NPC480910
0.6632	Remote Similarity	NPC240070
0.6632	Remote Similarity	NPC480909
0.6632	Remote Similarity	NPC608063
0.6569	Remote Similarity	NPC474908
0.6538	Remote Similarity	NPC474423
0.6531	Remote Similarity	NPC146857
0.6531	Remote Similarity	NPC486146
0.6517	Remote Similarity	NPC99620
0.6495	Remote Similarity	NPC55532
0.6444	Remote Similarity	NPC84987
0.6436	Remote Similarity	NPC486144
0.6436	Remote Similarity	NPC486145
0.6436	Remote Similarity	NPC486147
0.6436	Remote Similarity	NPC486136
0.6436	Remote Similarity	NPC486148
0.6374	Remote Similarity	NPC480915
0.6344	Remote Similarity	NPC179412
0.6344	Remote Similarity	NPC471356
0.6333	Remote Similarity	NPC471633
0.6237	Remote Similarity	NPC250556
0.6146	Remote Similarity	NPC173555
0.6095	Remote Similarity	NPC194716
0.6095	Remote Similarity	NPC486134
0.6095	Remote Similarity	NPC486141
0.6078	Remote Similarity	NPC476221
0.6078	Remote Similarity	NPC477709
0.6061	Remote Similarity	NPC475629
0.6	Remote Similarity	NPC59288
0.596	Remote Similarity	NPC486130
0.5941	Remote Similarity	NPC469749
0.5938	Remote Similarity	NPC193893
0.5914	Remote Similarity	NPC196429
0.59	Remote Similarity	NPC264336
0.59	Remote Similarity	NPC486127
0.59	Remote Similarity	NPC610296
0.5882	Remote Similarity	NPC247190
0.5851	Remote Similarity	NPC17896
0.5851	Remote Similarity	NPC469755
0.5851	Remote Similarity	NPC284406
0.5851	Remote Similarity	NPC197707
0.5851	Remote Similarity	NPC251866
0.5833	Remote Similarity	NPC483822
0.5833	Remote Similarity	NPC471353
0.5806	Remote Similarity	NPC473852
0.5743	Remote Similarity	NPC231518
0.5743	Remote Similarity	NPC488944
0.57	Remote Similarity	NPC40749
0.5684	Remote Similarity	NPC157376
0.5684	Remote Similarity	NPC142066
0.5684	Remote Similarity	NPC603972
0.566	Remote Similarity	NPC329636
0.5638	Remote Similarity	NPC99728
0.5638	Remote Similarity	NPC87250
0.5638	Remote Similarity	NPC244402
0.5638	Remote Similarity	NPC50305
0.5625	Remote Similarity	NPC243196
0.5625	Remote Similarity	NPC84949
0.5625	Remote Similarity	NPC480562
0.5625	Remote Similarity	NPC74945
0.5625	Remote Similarity	NPC31354
0.5625	Remote Similarity	NPC69576
0.5619	Remote Similarity	NPC486132
0.5619	Remote Similarity	NPC486131
0.5596	Remote Similarity	NPC329784
0.5566	Remote Similarity	NPC486128
0.5532	Remote Similarity	NPC474418
0.551	Remote Similarity	NPC305574
0.5421	Remote Similarity	NPC479360
0.5421	Remote Similarity	NPC479359
0.5421	Remote Similarity	NPC488943
0.5421	Remote Similarity	NPC488942
0.5417	Remote Similarity	NPC219085
0.5408	Remote Similarity	NPC146456
0.5364	Remote Similarity	NPC486140
0.5354	Remote Similarity	NPC484202
0.5315	Remote Similarity	NPC486133
0.5306	Remote Similarity	NPC199428
0.5306	Remote Similarity	NPC109448
0.5306	Remote Similarity	NPC310341
0.5278	Remote Similarity	NPC488938
0.5278	Remote Similarity	NPC488937
0.5253	Remote Similarity	NPC88668
0.5227	Remote Similarity	NPC196931
0.5208	Remote Similarity	NPC158344
0.52	Remote Similarity	NPC93883
0.5192	Remote Similarity	NPC479353
0.5192	Remote Similarity	NPC479354
0.5152	Remote Similarity	NPC604978
0.5143	Remote Similarity	NPC488941
0.5143	Remote Similarity	NPC488940
0.5133	Remote Similarity	NPC488945
0.5133	Remote Similarity	NPC488946
0.5102	Remote Similarity	NPC484211
0.51	Remote Similarity	NPC180079
0.5098	Remote Similarity	NPC488161
0.5098	Remote Similarity	NPC16569
0.5086	Remote Similarity	NPC486152
0.505	Remote Similarity	NPC9499
0.505	Remote Similarity	NPC471360
0.505	Remote Similarity	NPC469751
0.505	Remote Similarity	NPC471361
0.505	Remote Similarity	NPC86159
0.505	Remote Similarity	NPC469752
0.505	Remote Similarity	NPC469754
0.505	Remote Similarity	NPC277374
0.505	Remote Similarity	NPC70542

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC125077 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6253
0.1-0.2	2799
0.2-0.3	79
0.3-0.4	5
0.4-0.5	4
0.5-0.6	4
0.6-0.7	5
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
0.7111	Intermediate Similarity	NPD8294	Phase 4
0.6495	Remote Similarity	NPD8377	Phase 4
0.6237	Remote Similarity	NPD7507	Pre-clinical
0.6146	Remote Similarity	NPD8296	Phase 4
0.6064	Remote Similarity	NPD8335	Phase 4
0.6	Remote Similarity	NPD8380	Approved
0.5851	Remote Similarity	NPD7319	Approved
0.5743	Remote Similarity	NPD8033	Approved
0.5631	Remote Similarity	NPD8378	Pre-clinical
0.5631	Remote Similarity	NPD8379	Approved

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