NPASS Compound

Natural Product: NPC606320

Natural Product ID	NPC606320
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JXSVIVRDWWRQRT-BEELBYNOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL278622
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 83 87 0 0 0 0 0 0 0 0999 V2000 4.8971 3.2352 0.0065 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8885 1.7386 0.2822 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1482 1.0547 -1.0407 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2319 -0.3913 -0.6863 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8627 -0.9430 -0.2458 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2725 -2.2568 0.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9955 -2.4227 1.5828 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9292 -3.2296 -0.3371 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0925 -1.3205 -1.4617 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8634 -0.5657 -1.7604 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9467 -0.1946 -0.6285 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5477 1.2663 -0.9175 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6727 -0.1199 0.6444 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9436 -0.0671 1.7563 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5403 -0.0833 1.7212 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0385 -1.1005 0.6966 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5524 -0.9302 0.5759 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2171 -2.2369 0.1702 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1243 -0.5675 1.9308 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6227 -0.6712 1.7947 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1397 -0.3825 3.0831 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1936 0.2305 0.7409 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3638 -0.3748 0.2060 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2642 0.7079 -0.3092 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9786 0.4784 -1.6580 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2376 2.2541 -0.2299 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3803 2.7656 -1.1934 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8886 0.1740 -0.3547 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4262 -0.2684 -1.7054 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1209 -0.9207 -1.8076 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2905 -1.0881 -0.5742 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3453 -2.5008 -0.6520 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1840 -0.0934 0.7384 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5930 1.3316 0.8576 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5826 1.8037 2.3222 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5316 3.4708 -1.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3459 3.7896 0.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9605 3.5608 0.0778 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7060 1.4396 0.9693 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3163 1.3048 -1.7269 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0863 1.3674 -1.4954 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5699 -1.0185 -1.5351 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9558 -0.5164 0.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2720 -4.0631 0.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8964 -2.4368 -1.5493 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7659 -1.2026 -2.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1638 0.3339 -2.3864 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3041 -1.1822 -2.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3643 1.3534 -1.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4470 1.8687 -0.0228 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3569 1.7739 -1.5232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4943 -0.0108 2.7008 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8721 -0.4119 2.7519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0090 0.9118 1.6018 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9779 -2.0818 1.2706 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2868 -2.9210 1.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6849 -2.7801 -0.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2253 -2.0352 -0.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8874 0.4494 2.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8088 -1.3472 2.6509 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9130 -1.7532 1.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0471 -0.7140 3.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6395 1.0988 1.3220 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0631 0.2684 0.0255 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2383 -0.5594 -1.8321 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4881 1.0086 -2.4809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9674 1.0142 -1.5249 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8811 2.4814 0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2597 2.6593 -0.3213 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7828 3.5981 -1.5483 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2031 1.0203 -0.0440 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4939 0.6517 -2.3623 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2567 -0.9179 -2.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2607 -1.9160 -2.3330 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5104 -0.3545 -2.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1692 -2.5034 0.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3813 -3.2517 -0.2136 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5364 -2.8340 -1.6528 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3621 -0.5350 1.7557 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8118 1.9848 0.3668 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6270 2.2429 2.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3834 2.5121 2.5249 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8222 0.8713 2.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 1 6 7 2 0 6 8 1 0 5 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 22 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 24 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 6 13 33 1 0 33 34 1 0 34 35 1 0 34 2 1 0 33 5 1 0 31 11 1 0 31 16 1 0 28 17 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 1 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 8 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 12 49 1 0 12 50 1 0 12 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 18 56 1 0 18 57 1 0 18 58 1 0 19 59 1 0 19 60 1 0 20 61 1 6 21 62 1 0 22 63 1 1 23 64 1 0 25 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 32 76 1 0 32 77 1 0 32 78 1 0 33 79 1 0 34 80 1 6 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	JXSVIVRDWWRQRT-BEELBYNOSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-17-9-12-30(25(34)35)14-13-28(5)19(23(30)18(17)2)7-8-22-26(3)15-20(32)24(33)27(4,16-31)21(26)10-11-29(22,28)6/h7,17-18,20-24,31-33H,8-16H2,1-6H3,(H,34,35)/t17-,18+,20-,21?,22?,23?,24+,26+,27+,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)C(=CCC4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(CO)C5CC[C@]43C)C2[C@H]1C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	3.076 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.054 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.531 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.409	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.037	Fsp³:	0.9
MCE-18:	105.368 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.513	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.068 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.228	Promiscuous compounds:	0.033

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.53	MDCK Permeability:	-5.049
Pgp-inhibitor:	0.0	Pgp-substrate:	0.01
PAMPA:	1.0 ? 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):	0.001
20% Bioavailability (F20%):	0.275	30% Bioavailability (F30%):	0.015
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.613	MRP1:	0.856
Plasma Protein Binding (PPB):	76.017%	Volume Distribution (VD):	-0.4
Fu:	20.514% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.587	BCRP inhibitor:	0.148
BSEP inhibitor:	0.637

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.23	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? 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):

2.602

Half-life (T1/2):

1.528

ADMET: Toxicity

hERG Blockers:	0.026	hERG Blockers (10um):	0.063
Human Hepatotoxicity (H-HT):	0.623	Drug-induced Liver Injury (DILI):	0.097
AMES Toxicity:	0.059	Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.149	Skin Sensitization:	0.443
Carcinogencity:	0.522	Eye Corrosion:	0.0
Eye Irritation:	0.085	Respiratory Toxicity:	0.188
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.914
Hematotoxicity:	0.096	Drug-induced Nephrotoxicity:	0.545
Genotoxicity:	0.07	RPMI-8226 Immunitoxicity:	0.02
A549 Cytotoxicity:	0.054	Hek293 Cytotoxicity:	0.083
BCF:	1.032 ? 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:	3.756 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.45 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.589 ? 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
NPO58558	Siphoneugena densiflora	Species	Myrtaceae	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
Potency	4
Relative value	1
Tensile strength	1

Activity Type	# Activity
Individual protein	4
Organism	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT791	Individual protein	Cruzipain	Trypanosoma cruzi	Potency	=	28183.8	nM	PubChem BioAssay data set
NPT49	Individual protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT53	Individual protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	89125.1	nM	PubChem BioAssay data set

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
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Relative value	=	146.0	n.a.	DOI[10.1016/S0960-894X(96)00540-9]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Tensile strength	=	418.0	g cm**-2	DOI[10.1016/S0960-894X(96)00540-9]

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 NPC606320 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	23424
0.1-0.2	22854
0.2-0.3	2875
0.3-0.4	417
0.4-0.5	159
0.5-0.6	72
0.6-0.7	25
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC32407
1.0	High Similarity	NPC263548
0.8548	High Similarity	NPC71074
0.8548	High Similarity	NPC605937
0.8125	Intermediate Similarity	NPC305464
0.8125	Intermediate Similarity	NPC19376
0.8125	Intermediate Similarity	NPC25848
0.7761	Intermediate Similarity	NPC20235
0.7761	Intermediate Similarity	NPC299996
0.7692	Intermediate Similarity	NPC61543
0.7692	Intermediate Similarity	NPC293048
0.7692	Intermediate Similarity	NPC225585
0.7692	Intermediate Similarity	NPC88116
0.7576	Intermediate Similarity	NPC40092
0.7463	Intermediate Similarity	NPC247139
0.7424	Intermediate Similarity	NPC231063
0.7424	Intermediate Similarity	NPC282395
0.7424	Intermediate Similarity	NPC173744
0.7424	Intermediate Similarity	NPC204961
0.7424	Intermediate Similarity	NPC73004
0.7424	Intermediate Similarity	NPC37221
0.7424	Intermediate Similarity	NPC609452
0.7313	Intermediate Similarity	NPC87095
0.7246	Intermediate Similarity	NPC117663
0.7143	Intermediate Similarity	NPC479743
0.7015	Intermediate Similarity	NPC51700
0.7015	Intermediate Similarity	NPC88716
0.7015	Intermediate Similarity	NPC68160
0.6812	Remote Similarity	NPC173089
0.6712	Remote Similarity	NPC230151
0.662	Remote Similarity	NPC25299
0.662	Remote Similarity	NPC481322
0.6571	Remote Similarity	NPC477288
0.6479	Remote Similarity	NPC201657
0.6471	Remote Similarity	NPC274050
0.6471	Remote Similarity	NPC162632
0.6429	Remote Similarity	NPC472149
0.6429	Remote Similarity	NPC300351
0.6429	Remote Similarity	NPC110308
0.6377	Remote Similarity	NPC477289
0.6338	Remote Similarity	NPC259733
0.6338	Remote Similarity	NPC158371
0.6338	Remote Similarity	NPC207922
0.6338	Remote Similarity	NPC145667
0.6286	Remote Similarity	NPC84319
0.6286	Remote Similarity	NPC52021
0.6286	Remote Similarity	NPC599947
0.625	Remote Similarity	NPC88847
0.6143	Remote Similarity	NPC274330
0.6027	Remote Similarity	NPC9613
0.6027	Remote Similarity	NPC485589
0.6023	Remote Similarity	NPC479747
0.6023	Remote Similarity	NPC479746
0.5946	Remote Similarity	NPC127689
0.5946	Remote Similarity	NPC477290
0.5926	Remote Similarity	NPC57362
0.5867	Remote Similarity	NPC481318
0.5854	Remote Similarity	NPC177246
0.5833	Remote Similarity	NPC307282
0.5811	Remote Similarity	NPC191412
0.5811	Remote Similarity	NPC114159
0.5811	Remote Similarity	NPC6818
0.5769	Remote Similarity	NPC96693
0.5753	Remote Similarity	NPC481314
0.5733	Remote Similarity	NPC481316
0.5714	Remote Similarity	NPC485586
0.5714	Remote Similarity	NPC485588
0.5658	Remote Similarity	NPC116457
0.5652	Remote Similarity	NPC478657
0.5641	Remote Similarity	NPC481320
0.5618	Remote Similarity	NPC479744
0.5616	Remote Similarity	NPC270768
0.5616	Remote Similarity	NPC59263
0.5616	Remote Similarity	NPC210106
0.5616	Remote Similarity	NPC229281
0.5616	Remote Similarity	NPC121798
0.5616	Remote Similarity	NPC234346
0.557	Remote Similarity	NPC188833
0.557	Remote Similarity	NPC481319
0.5526	Remote Similarity	NPC607666
0.5526	Remote Similarity	NPC608261
0.5526	Remote Similarity	NPC611078
0.5495	Remote Similarity	NPC178093
0.5467	Remote Similarity	NPC136697
0.5395	Remote Similarity	NPC35239
0.5385	Remote Similarity	NPC481315
0.5385	Remote Similarity	NPC304110
0.5385	Remote Similarity	NPC27518
0.5385	Remote Similarity	NPC611516
0.5376	Remote Similarity	NPC479745
0.5366	Remote Similarity	NPC485585
0.5342	Remote Similarity	NPC43686
0.5333	Remote Similarity	NPC106112
0.5333	Remote Similarity	NPC261935
0.5333	Remote Similarity	NPC111214
0.5333	Remote Similarity	NPC481360
0.5325	Remote Similarity	NPC130520
0.5325	Remote Similarity	NPC62516
0.5263	Remote Similarity	NPC202728
0.5263	Remote Similarity	NPC158059
0.5263	Remote Similarity	NPC293564
0.52	Remote Similarity	NPC182797
0.52	Remote Similarity	NPC306541
0.52	Remote Similarity	NPC52169
0.52	Remote Similarity	NPC479079
0.52	Remote Similarity	NPC195019
0.52	Remote Similarity	NPC488562
0.5195	Remote Similarity	NPC132824
0.5195	Remote Similarity	NPC610635
0.5176	Remote Similarity	NPC485882
0.5155	Remote Similarity	NPC118033
0.5132	Remote Similarity	NPC38754
0.5128	Remote Similarity	NPC148964
0.5067	Remote Similarity	NPC480946
0.5067	Remote Similarity	NPC96916
0.5067	Remote Similarity	NPC187722
0.5067	Remote Similarity	NPC130577
0.5067	Remote Similarity	NPC142415
0.5067	Remote Similarity	NPC102683
0.5065	Remote Similarity	NPC256247
0.5065	Remote Similarity	NPC479077
0.5063	Remote Similarity	NPC187933
0.5063	Remote Similarity	NPC157113
0.5063	Remote Similarity	NPC174663
0.5063	Remote Similarity	NPC600832

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC606320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6497
0.1-0.2	2607
0.2-0.3	42
0.3-0.4	3
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