NPASS Compound

Natural Product: NPC582968

Natural Product ID	NPC582968
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Olean-12-ene-3,16-diol
IUPAC Name	(3~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{S},8~{a}~{S},12~{a}~{S},14~{b}~{R})-4,4,6~{a},6~{b},8~{a},11,11,14~{b}-octamethyl-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicene-3,8-diol
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 82 86 0 0 0 0 0 0 0 0999 V2000 -5.4679 1.8640 -1.5053 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9573 1.3165 -0.1771 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3386 2.3373 0.8752 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6675 0.0245 0.0584 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8431 -1.0154 0.7642 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5655 -1.3379 0.0096 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0656 -2.3208 -1.0811 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6989 -2.1564 0.8877 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9650 -3.5517 0.7409 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2241 -2.0646 0.7298 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7313 -0.6154 0.6858 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2751 0.0045 1.9711 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4552 -0.1078 -0.5057 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7803 0.3527 -1.5147 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7060 0.4232 -1.6024 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3673 -0.5498 -0.6822 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8570 -0.4026 -0.7587 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5143 -1.7139 -0.5384 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2566 -0.0319 -2.1993 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7315 0.2014 -2.3283 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3061 1.1492 -1.3418 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6964 1.0866 -1.4337 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8015 0.9975 0.0698 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9539 2.4059 0.6955 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6271 0.0907 0.9060 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3395 0.7614 0.0417 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6825 0.9281 1.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2102 0.7535 1.3453 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7475 -0.5171 0.6471 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2715 -1.6282 1.5731 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9433 -0.1306 -0.6086 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4600 1.2041 -0.1938 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5816 1.9661 -1.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2968 1.1659 -2.3306 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0613 2.8822 -1.6874 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7595 2.0768 1.8094 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4103 2.2660 1.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0371 3.3607 0.6073 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0570 -0.4079 -0.9022 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5684 0.2010 0.6834 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4908 -1.9395 0.8089 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6086 -0.7137 1.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1635 -2.5146 -1.7202 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3369 -3.2756 -0.6312 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8171 -1.8578 -1.7173 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9616 -2.0023 1.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7282 -3.8253 1.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7684 -2.6115 1.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9761 -2.5470 -0.2629 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3359 -0.1140 2.1287 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0805 1.1179 1.9766 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7835 -0.3804 2.8825 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3208 0.7294 -2.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9571 1.4655 -1.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9433 0.0910 -2.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1675 -1.5854 -1.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0481 -1.8690 0.3991 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7249 -2.5114 -0.7089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2666 -2.0127 -1.3248 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9660 -0.8817 -2.8363 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7565 0.8685 -2.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3577 -0.7028 -2.3851 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8597 0.6768 -3.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0427 2.1900 -1.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1435 0.7579 -0.6393 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9750 2.7688 0.4464 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2326 3.1037 0.2121 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8666 2.3693 1.7800 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5096 0.6863 1.2954 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1044 -0.2460 1.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1375 -0.7262 0.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9749 1.6748 -0.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8462 2.0179 1.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2139 0.4014 2.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8638 0.7299 2.4216 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7453 1.6629 0.9128 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3131 -1.3798 1.9352 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2074 -2.6191 1.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7139 -1.6581 2.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2532 -0.1879 -1.7055 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0449 1.6422 0.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1258 1.9397 -0.9958 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 6 6 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 13 31 1 0 31 32 1 0 32 2 1 0 31 6 1 0 29 11 1 0 29 16 1 0 26 17 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 7 43 1 0 7 44 1 0 7 45 1 0 8 46 1 1 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 6 22 65 1 0 24 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 25 71 1 0 26 72 1 6 27 73 1 0 27 74 1 0 28 75 1 0 28 76 1 0 30 77 1 0 30 78 1 0 30 79 1 0 31 80 1 6 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	VLRYIIPJIVGFIV-XSDXNTANSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-25(2)15-16-27(5)20(17-25)19-9-10-22-28(6)13-12-23(31)26(3,4)21(28)11-14-29(22,7)30(19,8)18-24(27)32/h9,20-24,31-32H,10-18H2,1-8H3/t20-,21-,22?,23-,24-,27-,28-,29+,30+/m0/s1
SMILES	CC1(C)CC[C@]2(C)[C@@H](O)C[C@]3(C)C(=CCC4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	5.037 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.33 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.906 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	26.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.391	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.723	Fsp³:	0.933
MCE-18:	104.897 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.636	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? 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:	0.534	Promiscuous compounds:	0.095

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.269	MDCK Permeability:	-4.931
Pgp-inhibitor:	0.66	Pgp-substrate:	0.054
PAMPA:	0.977 ? 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%):	0.866	30% Bioavailability (F30%):	0.229
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978	MRP1:	0.924
Plasma Protein Binding (PPB):	97.732%	Volume Distribution (VD):	-0.142
Fu:	2.638% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.972	BCRP inhibitor:	0.378
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.012	CYP1A2-substrate:	0.481
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.615
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.332	CYP2D6-substrate:	0.51
CYP3A4-inhibitor:	0.05	CYP3A4-substrate:	0.02
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.238
HLM stability:	0.989 ? 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):

12.226

Half-life (T1/2):

0.39

ADMET: Toxicity

hERG Blockers:	0.07	hERG Blockers (10um):	0.338
Human Hepatotoxicity (H-HT):	0.613	Drug-induced Liver Injury (DILI):	0.079
AMES Toxicity:	0.179	Rat Oral Acute Toxicity:	0.515
Maximum Recommended Daily Dose:	0.819	Skin Sensitization:	0.833
Carcinogencity:	0.903	Eye Corrosion:	0.006
Eye Irritation:	0.393	Respiratory Toxicity:	0.673
Drug-induced Neurotoxicity:	0.069	Ototoxicity:	0.612
Hematotoxicity:	0.13	Drug-induced Nephrotoxicity:	0.494
Genotoxicity:	0.401	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.486	Hek293 Cytotoxicity:	0.596
BCF:	2.386 ? 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:	4.446 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.573 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.19 ? 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
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	flowers	n.a.	n.a.	PMID[17190444]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327299]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28919	Calendula officinalis	Species	Asteraceae	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 NPC582968 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	26763
0.1-0.2	19444
0.2-0.3	2606
0.3-0.4	815
0.4-0.5	143
0.5-0.6	54
0.6-0.7	15
0.7-0.8	0
0.8-0.85	2
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	NPC34177
0.8	Intermediate Similarity	NPC253807
0.8	Intermediate Similarity	NPC158662
0.7593	Intermediate Similarity	NPC290598
0.7593	Intermediate Similarity	NPC30590
0.75	Intermediate Similarity	NPC311078
0.7213	Intermediate Similarity	NPC488519
0.7193	Intermediate Similarity	NPC101475
0.7069	Intermediate Similarity	NPC235341
0.6949	Remote Similarity	NPC230295
0.6949	Remote Similarity	NPC98386
0.6724	Remote Similarity	NPC474989
0.6721	Remote Similarity	NPC246708
0.6667	Remote Similarity	NPC159168
0.661	Remote Similarity	NPC132478
0.6333	Remote Similarity	NPC196753
0.629	Remote Similarity	NPC480950
0.623	Remote Similarity	NPC480924
0.6154	Remote Similarity	NPC7260
0.6154	Remote Similarity	NPC210037
0.6154	Remote Similarity	NPC120968
0.6154	Remote Similarity	NPC227467
0.6154	Remote Similarity	NPC273621
0.6129	Remote Similarity	NPC470588
0.597	Remote Similarity	NPC164349
0.5873	Remote Similarity	NPC238992
0.5833	Remote Similarity	NPC27765
0.5833	Remote Similarity	NPC122418
0.5833	Remote Similarity	NPC491014
0.5797	Remote Similarity	NPC294360
0.5735	Remote Similarity	NPC228784
0.5735	Remote Similarity	NPC324341
0.5735	Remote Similarity	NPC601810
0.5625	Remote Similarity	NPC253402
0.5625	Remote Similarity	NPC53744
0.5588	Remote Similarity	NPC18872
0.5588	Remote Similarity	NPC290614
0.5574	Remote Similarity	NPC120098
0.5556	Remote Similarity	NPC471433
0.5556	Remote Similarity	NPC283343
0.5556	Remote Similarity	NPC471432
0.5522	Remote Similarity	NPC480946
0.5522	Remote Similarity	NPC130577
0.5522	Remote Similarity	NPC142415
0.5522	Remote Similarity	NPC102683
0.5522	Remote Similarity	NPC136313
0.5522	Remote Similarity	NPC2539
0.5479	Remote Similarity	NPC473160
0.5469	Remote Similarity	NPC478657
0.5441	Remote Similarity	NPC171203
0.5441	Remote Similarity	NPC307426
0.5441	Remote Similarity	NPC98442
0.5441	Remote Similarity	NPC242468
0.5395	Remote Similarity	NPC167383
0.5323	Remote Similarity	NPC601696
0.5312	Remote Similarity	NPC237344
0.5286	Remote Similarity	NPC49776
0.5286	Remote Similarity	NPC63118
0.5286	Remote Similarity	NPC474436
0.5278	Remote Similarity	NPC488520
0.5231	Remote Similarity	NPC40394
0.5231	Remote Similarity	NPC291379
0.5231	Remote Similarity	NPC475862
0.5217	Remote Similarity	NPC112866
0.5211	Remote Similarity	NPC480919
0.5167	Remote Similarity	NPC472805
0.5167	Remote Similarity	NPC90979
0.5152	Remote Similarity	NPC95594
0.5147	Remote Similarity	NPC477872
0.5135	Remote Similarity	NPC86368
0.5135	Remote Similarity	NPC488522
0.5077	Remote Similarity	NPC1319
0.5072	Remote Similarity	NPC187722
0.5072	Remote Similarity	NPC213412
0.5072	Remote Similarity	NPC198664
0.5072	Remote Similarity	NPC610937
0.507	Remote Similarity	NPC202728
0.507	Remote Similarity	NPC158059

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC582968 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8122
0.1-0.2	986
0.2-0.3	37
0.3-0.4	4
0.4-0.5	0
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
0.5217	Remote Similarity	NPD7645	Phase 2

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