NPASS Compound

Natural Product: NPC479941

Natural Product ID	NPC479941
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PQVAFCDZYYLAEY-MGKOUKOVSA-N
IUPAC Name	n.a.
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 77 79 0 0 0 0 0 0 0 0999 V2000 6.1926 0.7684 -0.8812 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8088 1.2817 0.2567 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6661 0.8150 1.0275 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3856 1.4173 2.1625 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8462 -0.2874 0.5382 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4740 -0.3730 1.0217 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4101 0.5724 0.6222 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6728 2.0208 0.8844 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1264 0.4755 -0.8616 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1943 0.9224 -1.7678 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7363 -0.9215 -1.2530 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6046 -1.1508 -0.6272 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6207 -1.0053 0.8804 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0488 -0.9791 1.2670 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7397 0.1216 1.4064 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0637 1.4164 1.1788 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6741 1.3599 1.7946 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1177 0.1657 1.3893 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1432 1.9453 -0.0971 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8148 3.1101 -0.4531 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3938 3.7282 0.4572 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8619 3.6134 -1.8087 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5153 4.7223 -2.0788 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2258 5.5047 -1.0364 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1604 2.8547 -2.8810 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4234 -2.4216 1.5311 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7976 -3.1577 0.4403 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0395 -3.7646 0.3681 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8768 -3.6560 1.3199 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4843 -4.5721 -0.7981 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3274 -2.8095 2.2472 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2354 -2.3390 1.5059 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0450 -3.3471 0.5832 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1637 -4.1279 0.7053 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0033 -4.0079 1.6341 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4600 -5.2122 -0.3028 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0246 -2.4099 -1.0158 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7217 -0.0552 -1.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0774 1.2134 -1.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3827 2.1194 0.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5735 1.1737 2.8290 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0307 2.2549 2.4819 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3716 -1.2221 0.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9753 -0.4789 -0.5572 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5123 -0.3720 2.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1480 -1.4451 0.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9481 2.6651 0.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6326 2.3517 0.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7224 2.3496 1.9065 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2234 1.0966 -1.0297 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7173 1.5854 -2.5588 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5829 0.0713 -2.4120 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0025 1.5291 -1.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4786 -1.6928 -1.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5664 -0.8923 -2.3588 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3203 -0.4354 -1.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7936 0.0340 1.6868 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6582 2.1419 1.8272 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2476 2.3455 1.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9012 1.3197 2.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5613 -0.2247 2.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5473 5.1020 -3.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0689 4.9526 -0.5709 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6952 6.4034 -1.4956 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4953 5.9133 -0.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3692 3.3251 -3.8507 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5614 1.8054 -2.8256 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0749 2.8777 -2.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2789 -2.4255 2.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7790 -5.5946 -0.5061 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4011 -4.0572 -1.2020 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7281 -4.5521 -1.6011 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6060 -2.2771 2.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8113 -6.1292 0.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4827 -5.4822 -0.7506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1309 -4.8696 -1.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5665 -2.6986 -1.8611 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 22 25 1 0 14 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 26 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 12 37 1 0 18 7 1 0 18 13 1 0 32 13 1 0 1 38 1 0 1 39 1 0 2 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 8 47 1 0 8 48 1 0 8 49 1 0 9 50 1 0 10 51 1 0 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 12 56 1 0 15 57 1 0 16 58 1 1 17 59 1 0 17 60 1 0 18 61 1 0 23 62 1 0 24 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 25 67 1 0 25 68 1 0 26 69 1 1 30 70 1 0 30 71 1 0 30 72 1 0 32 73 1 1 36 74 1 0 36 75 1 0 36 76 1 0 37 77 1 0 M END

Standard InCHIKey	PQVAFCDZYYLAEY-MGKOUKOVSA-N
Standard InCHI	InChI=1S/C29H40O8/c1-9-16(3)11-12-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)17(4)10-2/h9-10,14,18,21,23-24,26-27,32H,1,3,11-13,15H2,2,4-8H3/b17-10-/t18?,21-,23?,24?,26-,27+,28?,29?/m0/s1
SMILES	C=CC(=C)CCC1(C)C(C)CC(C23C(=C[C@@H](CC12)OC(=O)/C(=CC)/C)[C@@H](OC(=O)C)O[C@H]3OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	516.27	Volume:	536.337 ? Van der Waals volume.
Dense:	0.963	LogP:	3.28 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.265 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.47 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	21.0
TPSA:	108.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.165	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.869	Fsp³:	0.621
MCE-18:	92.489 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.419	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.176 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.173	Promiscuous compounds:	0.085

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.996	MDCK Permeability:	-4.752
Pgp-inhibitor:	0.903	Pgp-substrate:	0.294
PAMPA:	0.189 ? 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):	0.029
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017	MRP1:	0.997
Plasma Protein Binding (PPB):	81.11%	Volume Distribution (VD):	-0.042
Fu:	14.644% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.987
OATP1B3 inhibitor:	0.906	BCRP inhibitor:	0.561
BSEP inhibitor:	0.968

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.865
CYP2C19-inhibitor:	0.116	CYP2C19-substrate:	0.293
CYP2C9-inhibitor:	0.104	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.05	CYP3A4-substrate:	0.064
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.987
HLM stability:	0.997 ? 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):

8.675

Half-life (T1/2):

1.223

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.317
Human Hepatotoxicity (H-HT):	0.522	Drug-induced Liver Injury (DILI):	0.837
AMES Toxicity:	0.976	Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.987	Skin Sensitization:	0.989
Carcinogencity:	0.587	Eye Corrosion:	0.0
Eye Irritation:	0.006	Respiratory Toxicity:	0.292
Drug-induced Neurotoxicity:	0.847	Ototoxicity:	0.556
Hematotoxicity:	0.219	Drug-induced Nephrotoxicity:	0.877
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.34
A549 Cytotoxicity:	0.737	Hek293 Cytotoxicity:	0.642
BCF:	1.024 ? 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:	4.045 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.998 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.306 ? 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
NPO40015	Anacolosa clarkii	Species	Aptandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30830773]

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
TGI	4

Activity Type	# Activity
Cell line	2
Others	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
NPT2276	Cell line	A673	Homo sapiens	TGI	=	1000.0	nM	PMID[30830773]
NPT15166	Cell line	Hep293TT	Homo sapiens	TGI	=	280.0	nM	PMID[30830773]
NPT2	Others	Unspecified	n.a.	TGI	=	440.0	nM	PMID[30830773]
NPT2	Others	Unspecified	n.a.	TGI	=	700.0	nM	PMID[30830773]

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 NPC479941 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	19302
0.1-0.2	25717
0.2-0.3	4649
0.3-0.4	72
0.4-0.5	39
0.5-0.6	34
0.6-0.7	30
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8689	High Similarity	NPC479943
0.8413	Intermediate Similarity	NPC479940
0.8413	Intermediate Similarity	NPC7644
0.8281	Intermediate Similarity	NPC475889
0.8281	Intermediate Similarity	NPC7613
0.8281	Intermediate Similarity	NPC479942
0.7727	Intermediate Similarity	NPC238397
0.7536	Intermediate Similarity	NPC127933
0.75	Intermediate Similarity	NPC471363
0.7067	Intermediate Similarity	NPC486751
0.7059	Intermediate Similarity	NPC609711
0.6866	Remote Similarity	NPC602188
0.68	Remote Similarity	NPC87630
0.6667	Remote Similarity	NPC479938
0.6571	Remote Similarity	NPC201880
0.6571	Remote Similarity	NPC479497
0.6571	Remote Similarity	NPC81567
0.6571	Remote Similarity	NPC329623
0.6571	Remote Similarity	NPC488652
0.6571	Remote Similarity	NPC609880
0.6479	Remote Similarity	NPC330003
0.6479	Remote Similarity	NPC217921
0.6479	Remote Similarity	NPC88013
0.6479	Remote Similarity	NPC470321
0.6479	Remote Similarity	NPC264867
0.6479	Remote Similarity	NPC135015
0.6479	Remote Similarity	NPC473207
0.6377	Remote Similarity	NPC488659
0.6377	Remote Similarity	NPC604149
0.6364	Remote Similarity	NPC179128
0.6338	Remote Similarity	NPC128795
0.6301	Remote Similarity	NPC488964
0.6301	Remote Similarity	NPC184512
0.625	Remote Similarity	NPC609715
0.6111	Remote Similarity	NPC134270
0.6111	Remote Similarity	NPC488660
0.6111	Remote Similarity	NPC488657
0.6111	Remote Similarity	NPC488654
0.6111	Remote Similarity	NPC479491
0.6027	Remote Similarity	NPC488658
0.6027	Remote Similarity	NPC488655
0.5867	Remote Similarity	NPC252296
0.5789	Remote Similarity	NPC125423
0.5775	Remote Similarity	NPC479934
0.5714	Remote Similarity	NPC40728
0.5634	Remote Similarity	NPC171598
0.5616	Remote Similarity	NPC488653
0.5616	Remote Similarity	NPC488656
0.561	Remote Similarity	NPC109376
0.5595	Remote Similarity	NPC224660
0.5526	Remote Similarity	NPC48548
0.5479	Remote Similarity	NPC479935
0.5479	Remote Similarity	NPC479936
0.5479	Remote Similarity	NPC318917
0.5479	Remote Similarity	NPC479939
0.5479	Remote Similarity	NPC481019
0.5417	Remote Similarity	NPC481018
0.5405	Remote Similarity	NPC488236
0.5405	Remote Similarity	NPC479937
0.5366	Remote Similarity	NPC116292
0.5333	Remote Similarity	NPC471366
0.5333	Remote Similarity	NPC476800
0.5333	Remote Similarity	NPC488237
0.5278	Remote Similarity	NPC472189
0.5263	Remote Similarity	NPC481017
0.5211	Remote Similarity	NPC476802
0.52	Remote Similarity	NPC472186
0.5195	Remote Similarity	NPC473545
0.5139	Remote Similarity	NPC89171
0.5135	Remote Similarity	NPC481020
0.5132	Remote Similarity	NPC488649
0.5067	Remote Similarity	NPC471362
0.5067	Remote Similarity	NPC471372
0.5065	Remote Similarity	NPC311223
0.5065	Remote Similarity	NPC316974

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7216
0.1-0.2	1881
0.2-0.3	53
0.3-0.4	0
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