NPASS Compound

Natural Product: NPC477727

Natural Product ID	NPC477727
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(4E,15E,26E)-triaconta-4,15,26-trien-1,12,29-triyne-3,28-diol
IUPAC Name	(4E,15E,26E)-triaconta-4,15,26-trien-1,12,29-triyne-3,28-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44558969
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 76 75 0 0 0 0 0 0 0 0999 V2000 -11.6934 1.7812 2.2899 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4489 1.8127 0.9920 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1636 1.8451 -0.5055 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0008 0.7608 -0.4470 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2295 0.5788 -1.4387 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0659 -0.4261 -1.5133 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0525 -0.9763 -0.0670 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9219 -1.8888 0.2457 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5901 -1.1478 0.1158 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4719 -2.0699 0.5085 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1162 -1.4741 0.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8118 -0.2603 0.9955 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6546 0.5714 0.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2754 0.1829 0.6970 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3057 -0.8996 -0.0237 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1035 -1.7165 -0.9574 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9391 -2.7739 -1.4685 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2208 -2.2776 -1.1963 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3428 -1.8258 -0.9428 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6941 -1.2600 -0.6186 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5843 0.1401 -1.2920 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6430 1.1089 -1.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0049 0.6763 -1.5222 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6713 -0.3412 -0.6742 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9206 0.0763 0.7157 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0603 1.1000 0.7962 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0471 0.8240 1.5906 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2081 1.6640 1.8307 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9386 3.0364 1.2113 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7658 4.0031 0.7668 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3475 1.1059 1.3844 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5392 3.0367 -0.7990 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8552 1.7711 3.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9316 1.4758 -1.0688 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9504 0.1212 0.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4323 1.0353 -2.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1008 -1.1849 -2.2032 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1870 0.2888 -1.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9361 -0.0441 0.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0171 -1.4679 0.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8958 -2.6964 -0.5682 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0090 -2.3968 1.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5777 -0.2546 0.7630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4017 -0.8325 -0.9267 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5741 -3.0271 -0.0758 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5362 -2.2951 1.5941 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1409 -1.2320 -0.8967 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3459 -2.2651 0.4088 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6659 0.4098 1.1694 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 -0.6471 2.0817 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7940 1.6442 0.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8499 0.6626 -0.5820 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4072 1.1421 0.5343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0781 0.0532 1.8311 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3832 -1.1572 0.4004 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -1.6347 -1.4603 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7290 -3.7389 -1.0057 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7401 -2.9401 -2.5752 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4298 -1.8587 -1.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8944 -1.2507 0.4012 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5762 0.5113 -0.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2886 -0.0470 -2.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5940 1.6315 -0.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4221 2.0109 -1.8453 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9425 0.2459 -2.5713 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7156 1.5354 -1.6487 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7615 -0.3865 -1.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3973 -1.3696 -0.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1308 -0.7930 1.3843 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0873 0.6190 1.2373 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9962 1.9353 0.1268 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9896 -0.1699 2.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1713 1.8090 2.9833 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5672 5.0899 0.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1260 1.4007 1.9838 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0831 3.3304 0.0515 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 3 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 2 0 27 28 1 0 28 29 1 0 29 30 3 0 28 31 1 0 3 32 1 0 1 33 1 0 3 34 1 0 4 35 1 0 5 36 1 0 6 37 1 0 6 38 1 0 7 39 1 0 7 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 9 44 1 0 10 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 20 59 1 0 20 60 1 0 21 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 27 72 1 0 28 73 1 0 30 74 1 0 31 75 1 0 32 76 1 0 M END

Standard InCHIKey	KNPRZNJIIPJQLW-RRCZHBAJSA-N
Standard InCHI	InChI=1S/C30H44O2/c1-3-29(31)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)4-2/h1-2,5-6,25-32H,7-9,11,13-24H2/b6-5+,27-25+,28-26+
SMILES	C#CC(/C=C/CCCCCCCCC/C=C/CC#CCCCCCC/C=C/C(C#C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	436.33	Volume:	521.288 ? Van der Waals volume.
Dense:	0.837	LogP:	5.688 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.6 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.589 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	6.0
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:	0.131	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.192	Fsp³:	0.6
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:	0.643	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.67	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.045	MDCK Permeability:	-4.59
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.056 ? 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):	0.175
20% Bioavailability (F20%):	0.025	30% Bioavailability (F30%):	0.528
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	99.715%	Volume Distribution (VD):	0.158
Fu:	0.041% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.043
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.972
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.696
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.987
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.644
CYP2D6-inhibitor:	0.015	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.042	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.485 ? 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):

4.426

Half-life (T1/2):

0.797

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.517
Human Hepatotoxicity (H-HT):	0.94	Drug-induced Liver Injury (DILI):	0.017
AMES Toxicity:	0.027	Rat Oral Acute Toxicity:	0.55
Maximum Recommended Daily Dose:	0.641	Skin Sensitization:	0.967
Carcinogencity:	0.016	Eye Corrosion:	0.0
Eye Irritation:	0.109	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.065	Ototoxicity:	0.921
Hematotoxicity:	0.008	Drug-induced Nephrotoxicity:	0.912
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.315
A549 Cytotoxicity:	0.029	Hek293 Cytotoxicity:	0.364
BCF:	0.836 ? 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:	5.575 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.56 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.99 ? 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]
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]
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]
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
ED50	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
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.4	ug/ml	PMID[10217707]
NPT146	Cell line	SK-OV-3	Homo sapiens	ED50	=	0.1	ug/ml	PMID[10217707]
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	=	0.2	ug/ml	PMID[10217707]
NPT574	Cell line	XF498	Homo sapiens	ED50	=	1.2	ug/ml	PMID[10217707]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	=	1.2	ug/ml	PMID[10217707]

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 NPC477727 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	43628
0.1-0.2	5627
0.2-0.3	461
0.3-0.4	52
0.4-0.5	41
0.5-0.6	18
0.6-0.7	21
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
0.7895	Intermediate Similarity	NPC477726
0.7895	Intermediate Similarity	NPC477725
0.7	Intermediate Similarity	NPC170776
0.7	Intermediate Similarity	NPC9273
0.7	Intermediate Similarity	NPC165447
0.7	Intermediate Similarity	NPC471959
0.7	Intermediate Similarity	NPC199286
0.7	Intermediate Similarity	NPC489046
0.7	Intermediate Similarity	NPC76198
0.7	Intermediate Similarity	NPC610719
0.6857	Remote Similarity	NPC55383
0.6842	Remote Similarity	NPC89824
0.6842	Remote Similarity	NPC475477
0.6842	Remote Similarity	NPC256656
0.6842	Remote Similarity	NPC294278
0.6842	Remote Similarity	NPC477723
0.6774	Remote Similarity	NPC607242
0.6667	Remote Similarity	NPC125122
0.6667	Remote Similarity	NPC471276
0.6667	Remote Similarity	NPC471280
0.6667	Remote Similarity	NPC471281
0.6667	Remote Similarity	NPC474513
0.6579	Remote Similarity	NPC197272
0.6364	Remote Similarity	NPC474642
0.6364	Remote Similarity	NPC473913
0.619	Remote Similarity	NPC224148
0.6098	Remote Similarity	NPC48058
0.6061	Remote Similarity	NPC249670
0.6047	Remote Similarity	NPC473896
0.6047	Remote Similarity	NPC473735
0.6047	Remote Similarity	NPC329608
0.5909	Remote Similarity	NPC473847
0.5909	Remote Similarity	NPC473721
0.5909	Remote Similarity	NPC473725
0.5909	Remote Similarity	NPC473910
0.5909	Remote Similarity	NPC475384
0.5909	Remote Similarity	NPC473532
0.5682	Remote Similarity	NPC470969
0.5652	Remote Similarity	NPC473652
0.5556	Remote Similarity	NPC311648
0.5556	Remote Similarity	NPC474644
0.5526	Remote Similarity	NPC161838
0.5435	Remote Similarity	NPC152668
0.5385	Remote Similarity	NPC471960
0.5306	Remote Similarity	NPC168407
0.525	Remote Similarity	NPC187361
0.5128	Remote Similarity	NPC471239
0.5128	Remote Similarity	NPC474643
0.5128	Remote Similarity	NPC473865

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8686
0.1-0.2	446
0.2-0.3	17
0.3-0.4	1
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