NPASS Compound

Natural Product: NPC9273

Natural Product ID	NPC9273
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(-)-Duryne B
IUPAC Name	(3R,4E,15Z,28E,30R)-dotriaconta-4,15,28-trien-1,31-diyne-3,30-diol
Synonyms	(-)-Duryne B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1801789
PubChem CID	53354921
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

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 86 85 0 0 0 0 0 0 0 0999 V2000 -10.2788 -0.0403 1.6965 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9946 -0.0935 0.7046 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8526 -0.1774 -0.4753 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7879 0.4545 -1.4940 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9821 -0.4243 -1.9310 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8167 -0.1995 -2.8900 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6218 -0.8569 -2.0667 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5988 -0.1955 -0.7181 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4373 -0.5866 0.1733 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1214 -0.4439 -0.5694 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8588 0.9745 -0.9537 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5368 1.9278 0.1253 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1971 1.9315 0.7148 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5622 0.7191 1.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3809 1.2444 2.0043 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1557 0.9534 1.7008 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2231 0.0551 0.6087 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0440 -1.0765 1.3287 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1225 -0.4052 2.1497 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1288 0.3432 1.3325 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9965 -0.6248 0.5371 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9049 0.1168 -0.4348 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7058 1.1543 0.1518 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6468 1.0113 1.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8682 0.1808 1.1794 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5629 -1.2816 0.9661 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9585 -1.9954 0.8599 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6196 -1.2577 -0.1826 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6352 -0.6157 -0.5476 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5313 -0.0076 -2.0617 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9075 0.1022 -2.5881 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9431 0.1862 -2.9802 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1726 1.2895 -1.7195 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1299 -1.4586 -0.8367 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6085 0.0063 2.6596 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6796 0.5198 -0.4193 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8680 1.4716 -1.6208 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1244 -1.5421 -1.8114 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5041 0.9114 -2.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8689 -0.5383 -3.8579 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8711 -1.9008 -1.9873 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7640 -0.6575 -2.6904 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4451 -0.7804 -0.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9173 0.8109 -0.6343 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5119 -1.5737 0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4097 0.1236 1.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0568 -1.1922 -1.3995 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3438 -0.7971 0.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7890 1.4281 -1.4677 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0794 0.9994 -1.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7721 3.0102 -0.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3177 1.7839 0.9495 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1435 2.7638 1.4903 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4376 2.3534 -0.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3207 -0.0812 0.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2830 0.2977 2.0704 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5751 1.9032 2.8867 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6905 1.4370 2.2398 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5631 -0.3905 0.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9367 0.5564 -0.0615 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3787 -1.6742 1.9503 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5171 -1.7000 0.5550 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6873 -1.2875 2.5789 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7682 0.1292 3.0251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7592 0.9062 2.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7690 1.0923 0.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3550 -1.2813 -0.0393 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5865 -1.2690 1.2589 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1828 0.6199 -1.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4244 -0.6477 -1.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0718 2.1103 0.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3674 1.5675 -0.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9751 2.0834 1.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1301 0.6764 2.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4098 0.5384 0.2455 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5414 0.2859 2.0671 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9355 -1.7257 1.7120 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1338 -1.5079 -0.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6975 -3.0542 0.5131 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4000 -2.0122 1.8327 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8558 -1.3583 -1.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4787 -0.4427 -0.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8626 -0.5824 -2.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 14.0957 0.2592 -3.4079 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1701 1.5862 -0.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5845 -1.5236 -1.7145 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 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 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 3 0 30 33 1 0 3 34 1 0 1 35 1 0 3 36 1 1 4 37 1 0 5 38 1 0 6 39 1 0 6 40 1 0 7 41 1 0 7 42 1 0 8 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 0 14 56 1 0 15 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 0 18 62 1 0 19 63 1 0 19 64 1 0 20 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 22 69 1 0 22 70 1 0 23 71 1 0 23 72 1 0 24 73 1 0 24 74 1 0 25 75 1 0 25 76 1 0 26 77 1 0 26 78 1 0 27 79 1 0 27 80 1 0 28 81 1 0 29 82 1 0 30 83 1 6 32 84 1 0 33 85 1 0 34 86 1 0 M END

Standard InCHIKey	ZEWIWYQCBPUQNR-JIHXWXSTSA-N
Standard InCHI	InChI=1S/C32H52O2/c1-3-31(33)29-27-25-23-21-19-17-15-13-11-9-7-5-6-8-10-12-14-16-18-20-22-24-26-28-30-32(34)4-2/h1-2,5,7,27-34H,6,8-26H2/b7-5-,29-27+,30-28+/t31-,32-/m0/s1
SMILES	C#C[C@@H](/C=C/CCCCCCCCC/C=CCCCCCCCCCCC/C=C/[C@H](C#C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.4	Volume:	561.153 ? Van der Waals volume.
Dense:	0.835	LogP:	7.861 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.432 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.952 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	5.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.085	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.574	Fsp³:	0.688
MCE-18:	2.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.656	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.706	Promiscuous compounds:	0.046

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.021	MDCK Permeability:	-4.616
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.0 ? 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):	0.004
20% Bioavailability (F20%):	0.006	30% Bioavailability (F30%):	0.818
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	100.217%	Volume Distribution (VD):	0.218
Fu:	0.047% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.012
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.994
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.582
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.028	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.035 ? 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):

4.129

Half-life (T1/2):

1.189

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.619
Human Hepatotoxicity (H-HT):	0.55	Drug-induced Liver Injury (DILI):	0.001
AMES Toxicity:	0.039	Rat Oral Acute Toxicity:	0.179
Maximum Recommended Daily Dose:	0.889	Skin Sensitization:	1.0
Carcinogencity:	0.408	Eye Corrosion:	0.002
Eye Irritation:	0.576	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.039	Ototoxicity:	0.889
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.789
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.633
A549 Cytotoxicity:	0.863	Hek293 Cytotoxicity:	0.74
BCF:	0.489 ? 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:	5.309 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.422 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.151 ? 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
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	(15-25 m depth) off Komun Island, Korea	1995-JUL	PMID[10217707]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346968]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514299]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170665]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754614]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	1996	PMID[18327911]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	Miyako sea-knoll, southwestern Japan (2525.64' N, 12542.48' E), at a depth of 415 m	2009-OCT	PMID[21534590]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21534590]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	American Samoa	n.a.	PMID[23368996]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[26821210]
NPO30927	Petrosia	Genus	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784165]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917297]
NPO32667	Petrosia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	5

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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	260.0	nM	PMID[21534590]
NPT168	Cell line	P388	Mus musculus	IC50	=	160.0	nM	PMID[21534590]
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	160.0	nM	PMID[21534590]
NPT81	Cell line	A549	Homo sapiens	IC50	=	160.0	nM	PMID[21534590]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	160.0	nM	PMID[21534590]

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 NPC9273 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	40721
0.1-0.2	8252
0.2-0.3	677
0.3-0.4	105
0.4-0.5	40
0.5-0.6	29
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC170776
1.0	High Similarity	NPC165447
1.0	High Similarity	NPC471959
1.0	High Similarity	NPC199286
1.0	High Similarity	NPC489046
1.0	High Similarity	NPC76198
1.0	High Similarity	NPC610719
0.9545	High Similarity	NPC607242
0.9524	High Similarity	NPC125122
0.9524	High Similarity	NPC471276
0.9524	High Similarity	NPC471280
0.9524	High Similarity	NPC471281
0.875	High Similarity	NPC474642
0.875	High Similarity	NPC473913
0.8333	Intermediate Similarity	NPC249670
0.7407	Intermediate Similarity	NPC474644
0.7241	Intermediate Similarity	NPC161838
0.7	Intermediate Similarity	NPC471960
0.7	Intermediate Similarity	NPC477727
0.6667	Remote Similarity	NPC471239
0.6667	Remote Similarity	NPC474643
0.6667	Remote Similarity	NPC473865
0.6667	Remote Similarity	NPC55383
0.6364	Remote Similarity	NPC197272
0.6176	Remote Similarity	NPC89824
0.6176	Remote Similarity	NPC475477
0.6176	Remote Similarity	NPC256656
0.6176	Remote Similarity	NPC294278
0.6176	Remote Similarity	NPC477723
0.6	Remote Similarity	NPC470966
0.5833	Remote Similarity	NPC48058
0.5833	Remote Similarity	NPC470963
0.5833	Remote Similarity	NPC477661
0.5833	Remote Similarity	NPC603233
0.5833	Remote Similarity	NPC607245
0.5556	Remote Similarity	NPC471278
0.5526	Remote Similarity	NPC224148
0.5526	Remote Similarity	NPC477726
0.5526	Remote Similarity	NPC477725
0.5484	Remote Similarity	NPC124183
0.5484	Remote Similarity	NPC482802
0.5385	Remote Similarity	NPC473896
0.5385	Remote Similarity	NPC473735
0.5385	Remote Similarity	NPC146551
0.5385	Remote Similarity	NPC329608
0.5333	Remote Similarity	NPC600749
0.5333	Remote Similarity	NPC601019
0.5312	Remote Similarity	NPC91226
0.5312	Remote Similarity	NPC243546
0.5312	Remote Similarity	NPC31194
0.5312	Remote Similarity	NPC248884
0.5263	Remote Similarity	NPC470970
0.525	Remote Similarity	NPC473847
0.525	Remote Similarity	NPC473721
0.525	Remote Similarity	NPC473725
0.525	Remote Similarity	NPC473910
0.525	Remote Similarity	NPC475384
0.525	Remote Similarity	NPC473532
0.5152	Remote Similarity	NPC72699

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC9273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8440
0.1-0.2	670
0.2-0.3	34
0.3-0.4	5
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