NPASS Compound

Natural Product: NPC470966

Natural Product ID	NPC470966
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(-)-Pellynol A
IUPAC Name	(18Z,29E)-tritriaconta-18,29-dien-2,4,32-triyne-1,6,31-triol
Synonyms	(-)-Pellynol A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2333788
PubChem CID	11799453
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 88 87 0 0 0 0 0 0 0 0999 V2000 -14.0297 2.1348 0.7601 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1859 0.9600 0.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6218 0.2063 -0.4613 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2363 0.6818 -1.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1126 0.0914 -0.8261 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8763 0.7290 -1.4640 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9756 1.0698 -0.2905 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3735 -0.0655 0.4511 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1471 -0.7242 -0.1812 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7385 -1.7492 0.8226 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3277 -2.2982 0.6481 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4040 -1.0266 0.7632 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7424 -0.2707 2.0333 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8459 0.9973 2.0537 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0647 1.6815 0.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0812 1.9616 -0.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6991 1.5746 0.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1821 0.5798 -0.8497 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1517 0.0998 -0.3372 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8243 -0.8096 -1.2806 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0966 -1.3533 -0.6466 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9272 -0.1863 -0.1301 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2416 -0.7135 0.3829 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9301 0.4985 1.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3026 0.1554 1.4749 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2115 -0.1735 0.3031 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2950 1.0551 -0.5707 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1180 0.7801 -1.7755 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4538 0.3524 -1.5429 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6888 -0.0243 -1.3210 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9369 -0.3954 -1.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0881 -0.7266 -0.8587 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4242 -1.1089 -0.5662 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6260 -1.2868 0.8371 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1679 1.9733 -2.5411 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0986 -0.9784 0.3044 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.4633 2.7355 1.1334 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9973 -0.4272 -1.4179 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3315 1.5718 -1.6615 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0107 -0.8219 -0.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5033 -0.0139 -2.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1743 1.6534 -1.9578 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1935 1.7917 -0.6150 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6499 1.6075 0.4651 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1603 0.2250 1.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1397 -0.8850 0.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4089 -1.1373 -1.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3566 0.0332 -0.4214 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9044 -1.4722 1.8760 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4042 -2.6544 0.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1077 -2.8234 1.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0927 -2.7854 -0.2511 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3819 -0.4193 -0.0989 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3641 -1.5040 0.8290 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7688 0.0874 1.9692 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5374 -0.8639 2.9745 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8779 0.6257 2.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1719 1.6527 2.9379 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0653 1.9991 0.4954 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3334 2.5292 -0.9987 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5498 1.2575 1.2182 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0300 2.4899 0.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8895 -0.2365 -1.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0159 1.0641 -1.8153 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7328 1.0514 -0.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9678 -0.3435 0.6883 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0894 -0.3661 -2.2548 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1337 -1.6899 -1.4376 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6778 -1.8473 -1.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8885 -2.0420 0.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1489 0.5437 -0.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4200 0.3510 0.7182 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1304 -1.5484 1.1293 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8541 -0.9746 -0.4576 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7876 1.3554 0.4315 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2831 0.6950 1.9692 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2549 -0.8062 2.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7704 0.9057 2.1589 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8397 -1.0436 -0.2245 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1939 -0.3406 0.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7508 1.9250 -0.0564 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2626 1.3883 -0.8830 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5771 -0.0108 -2.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6847 -2.1288 -0.9680 H 0 0 0 0 0 0 0 0 0 0 0 0 16.0963 -0.3159 -0.8462 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9843 -0.7535 1.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9617 2.4689 -2.1511 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3478 -0.7599 1.2676 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 3 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 3 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 1 0 29 30 3 0 30 31 1 0 31 32 3 0 32 33 1 0 33 34 1 0 28 35 1 0 3 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 9 48 1 0 10 49 1 0 10 50 1 0 11 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 13 55 1 0 13 56 1 0 14 57 1 0 14 58 1 0 15 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 0 18 64 1 0 19 65 1 0 19 66 1 0 20 67 1 0 20 68 1 0 21 69 1 0 21 70 1 0 22 71 1 0 22 72 1 0 23 73 1 0 23 74 1 0 24 75 1 0 24 76 1 0 25 77 1 0 25 78 1 0 26 79 1 0 26 80 1 0 27 81 1 0 27 82 1 0 28 83 1 0 33 84 1 0 33 85 1 0 34 86 1 0 35 87 1 0 36 88 1 0 M END

Standard InCHIKey	XZPARIIPCPBWHJ-VTHIMXSSSA-N
Standard InCHI	InChI=1S/C33H52O3/c1-2-32(35)28-24-21-19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-22-25-29-33(36)30-26-23-27-31-34/h1,3-4,24,28,32-36H,5-22,25,29,31H2/b4-3-,28-24+
SMILES	C#CC(C=CCCCCCCCCCC=CCCCCCCCCCCCC(C#CC#CCO)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	496.39	Volume:	584.603 ? Van der Waals volume.
Dense:	0.849	LogP:	7.565 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.312 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.499 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	5.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.079	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.018	Fsp³:	0.697
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:	0.637	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? 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:	0.664	Promiscuous compounds:	0.012

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.057	MDCK Permeability:	-4.747
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.039 ? 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):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	98.857%	Volume Distribution (VD):	0.542
Fu:	0.222% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	1.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.995
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.74	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.004 ? 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):

3.418

Half-life (T1/2):

1.776

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.804
Human Hepatotoxicity (H-HT):	0.254	Drug-induced Liver Injury (DILI):	0.436
AMES Toxicity:	0.094	Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.966	Skin Sensitization:	1.0
Carcinogencity:	0.083	Eye Corrosion:	1.0
Eye Irritation:	0.998	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.667
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.176
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.103
A549 Cytotoxicity:	0.009	Hek293 Cytotoxicity:	0.486
BCF:	0.775 ? 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:	5.682 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.609 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.433 ? 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
Ratio IC50	1
IC50	4

Activity Type	# Activity
Cell line	3
Non-molecular	2

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
NPT1383	Cell line	A2058	Homo sapiens	Ratio IC50	=	1.0	n.a.	PMID[23368996]
NPT1383	Cell line	A2058	Homo sapiens	IC50	=	400.0	nM	PMID[9036182]
NPT4490	Cell line	IMR-90	Homo sapiens	IC50	=	400.0	nM	PMID[2045816]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	800.0	nM	PMID[23368996]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	400.0	nM	PMID[23368996]

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 NPC470966 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	34969
0.1-0.2	13991
0.2-0.3	707
0.3-0.4	101
0.4-0.5	46
0.5-0.6	21
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC477661
0.9722	High Similarity	NPC603233
0.9722	High Similarity	NPC607245
0.8947	High Similarity	NPC470970
0.85	High Similarity	NPC470969
0.7556	Intermediate Similarity	NPC470967
0.7556	Intermediate Similarity	NPC470968
0.7391	Intermediate Similarity	NPC601905
0.7391	Intermediate Similarity	NPC603973
0.7143	Intermediate Similarity	NPC603237
0.6829	Remote Similarity	NPC610169
0.6	Remote Similarity	NPC170776
0.6	Remote Similarity	NPC9273
0.6	Remote Similarity	NPC165447
0.6	Remote Similarity	NPC471959
0.6	Remote Similarity	NPC199286
0.6	Remote Similarity	NPC489046
0.6	Remote Similarity	NPC76198
0.6	Remote Similarity	NPC610719
0.5946	Remote Similarity	NPC474642
0.5946	Remote Similarity	NPC473913
0.5833	Remote Similarity	NPC607242
0.5714	Remote Similarity	NPC125122
0.5714	Remote Similarity	NPC471276
0.5714	Remote Similarity	NPC471280
0.5714	Remote Similarity	NPC471281
0.5676	Remote Similarity	NPC249670
0.561	Remote Similarity	NPC161838
0.561	Remote Similarity	NPC72699
0.5581	Remote Similarity	NPC484320
0.5476	Remote Similarity	NPC471960
0.5385	Remote Similarity	NPC600749
0.5385	Remote Similarity	NPC601019
0.5333	Remote Similarity	NPC602871
0.5333	Remote Similarity	NPC606346
0.5319	Remote Similarity	NPC603017
0.5306	Remote Similarity	NPC473532
0.5227	Remote Similarity	NPC168510
0.5208	Remote Similarity	NPC477726
0.5116	Remote Similarity	NPC153538

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8284
0.1-0.2	836
0.2-0.3	29
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