NPASS Compound

Natural Product: NPC555495

Natural Product ID	NPC555495
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Baumycin C2
IUPAC Name	~{N}-[(2~{R},3~{R},4~{S},6~{R})-3-hydroxy-2-methyl-6-[[(1~{R},3~{R})-3,5,12-trihydroxy-3-[(1~{S})-1-hydroxyethyl]-10-methoxy-6,11-dioxo-2,4-dihydro-1~{H}-tetracen-1-yl]oxy]tetrahydropyran-4-yl]formamide
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 71 75 0 0 0 0 0 0 0 0999 V2000 4.7921 -4.7925 2.9258 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2266 -3.6648 2.3111 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0032 -2.9091 1.4553 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3103 -3.2212 1.1827 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1036 -2.4792 0.3303 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5359 -1.3713 -0.2685 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2121 -1.0130 -0.0234 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4709 -1.7856 0.8313 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0912 -1.3990 1.0774 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4050 -2.1149 1.8687 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4912 -0.2337 0.4495 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1753 0.1007 0.7096 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4332 -0.6927 1.5816 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5765 1.2083 0.1236 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3482 1.9613 -0.7272 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8234 3.1763 -1.3943 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6702 3.1434 -1.3673 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0776 1.9996 -2.0629 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3114 4.3335 -2.0129 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8693 5.6410 -1.4544 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6919 4.1900 -1.9462 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1117 2.9595 0.0709 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8342 1.5014 0.4425 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6497 0.6575 -0.2761 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5530 -0.0753 0.4834 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9625 0.2690 0.1004 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7419 -0.8957 -0.4598 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1344 -0.5508 -0.5083 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8457 -0.3721 -1.7022 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2134 -0.5262 -2.7673 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4339 -2.1901 0.2017 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0984 -3.1546 -0.7655 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2074 -2.1052 1.0888 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7234 -3.4759 1.4922 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2579 -1.4191 0.3301 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6138 -0.9851 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4682 2.3772 -1.8492 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2650 0.5189 -0.4030 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6602 0.1662 -0.6801 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3362 0.8844 -1.4699 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3425 -5.4204 2.1889 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4916 -4.5475 3.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9711 -5.4350 3.3461 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7890 -4.0910 1.6408 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1253 -2.7332 0.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0984 -0.7379 -0.9522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5340 -0.6293 2.5872 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2169 4.0374 -0.7736 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2260 3.2545 -2.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4758 1.9364 -2.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0533 4.3193 -3.0989 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3202 5.5718 -0.5073 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7467 6.2888 -1.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1911 6.1923 -2.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9593 3.2586 -2.1355 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1545 3.2253 0.2118 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4475 3.5742 0.7037 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0679 1.4010 1.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3702 0.1894 1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9247 1.1209 -0.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4804 0.6479 1.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4237 -0.9781 -1.5215 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5935 -0.4396 0.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8900 -0.1137 -1.7269 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3001 -2.6301 0.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8459 -3.7582 -0.9731 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3662 -1.5167 2.0007 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9763 -4.2586 0.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6457 -3.5280 1.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2320 -3.7976 2.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6463 3.3371 -1.5280 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 19 21 1 0 17 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 2 0 27 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 15 36 1 0 36 37 1 0 36 38 2 0 38 39 1 0 39 40 2 0 8 3 1 0 38 11 1 0 39 7 1 0 23 14 1 0 35 25 1 0 1 41 1 0 1 42 1 0 1 43 1 0 4 44 1 0 5 45 1 0 6 46 1 0 13 47 1 0 16 48 1 0 16 49 1 0 18 50 1 0 19 51 1 6 20 52 1 0 20 53 1 0 20 54 1 0 21 55 1 0 22 56 1 0 22 57 1 0 23 58 1 1 25 59 1 1 26 60 1 0 26 61 1 0 27 62 1 6 28 63 1 0 29 64 1 0 31 65 1 1 32 66 1 0 33 67 1 1 34 68 1 0 34 69 1 0 34 70 1 0 37 71 1 0 M END

Standard InCHIKey	STAZCZIPHWGTBD-ZIMMSHDSSA-N
Standard InCHI	InChI=1S/C28H31NO11/c1-11-23(32)15(29-10-30)7-18(39-11)40-17-9-28(37,12(2)31)8-14-20(17)27(36)22-21(25(14)34)24(33)13-5-4-6-16(38-3)19(13)26(22)35/h4-6,10-12,15,17-18,23,31-32,34,36-37H,7-9H2,1-3H3,(H,29,30)/t11-,12+,15+,17-,18+,23+,28-/m1/s1
SMILES	COC1=CC=CC2=C1C(=O)C1=C(O)C3=C(C[C@](O)([C@H](C)O)C[C@H]3O[C@H]3C[C@H](NC=O)[C@@H](O)[C@@H](C)O3)C(O)=C1C2=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	557.19	Volume:	534.023 ? Van der Waals volume.
Dense:	1.043	LogP:	1.972 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.346 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.851 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	192.08 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.184	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.782	Fsp³:	0.464
MCE-18:	120.366 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	1
Colloidal aggregators:	0.518	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.328 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.552 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.008	Promiscuous compounds:	0.499

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.028	MDCK Permeability:	-5.199
Pgp-inhibitor:	0.013	Pgp-substrate:	0.989
PAMPA:	0.999 ? 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):	0.964
20% Bioavailability (F20%):	0.987	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.884
Plasma Protein Binding (PPB):	93.994%	Volume Distribution (VD):	0.641
Fu:	6.797% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.166
BSEP inhibitor:	0.27

ADMET: Metabolism

CYP1A2-inhibitor:	0.079	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.016	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.157
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.425
HLM stability:	0.128 ? 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):

5.917

Half-life (T1/2):

4.439

ADMET: Toxicity

hERG Blockers:	0.087	hERG Blockers (10um):	0.244
Human Hepatotoxicity (H-HT):	0.976	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.996	Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.963	Skin Sensitization:	0.997
Carcinogencity:	0.898	Eye Corrosion:	0.0
Eye Irritation:	0.011	Respiratory Toxicity:	0.879
Drug-induced Neurotoxicity:	0.665	Ototoxicity:	0.951
Hematotoxicity:	0.798	Drug-induced Nephrotoxicity:	0.979
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.685
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.909
BCF:	0.453 ? 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:	3.276 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.111 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.102 ? 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
NPO49558	Streptomyces griseus (FCRC-48)	Genus	Streptomycetaceae	Bacteria	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

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

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 NPC555495 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	13122
0.1-0.2	35585
0.2-0.3	1110
0.3-0.4	29
0.4-0.5	4
0.5-0.6	1
0.6-0.7	7
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
0.7558	Intermediate Similarity	NPC600087
0.6744	Remote Similarity	NPC603200
0.6705	Remote Similarity	NPC601855
0.6292	Remote Similarity	NPC109403
0.6264	Remote Similarity	NPC261012
0.6264	Remote Similarity	NPC314738
0.6222	Remote Similarity	NPC487573
0.6196	Remote Similarity	NPC468994
0.5054	Remote Similarity	NPC602774

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC555495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3181
0.1-0.2	5902
0.2-0.3	37
0.3-0.4	3
0.4-0.5	8
0.5-0.6	11
0.6-0.7	6
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
0.6292	Remote Similarity	NPD6778	Phase 4
0.6264	Remote Similarity	NPD6781	Phase 4
0.6264	Remote Similarity	NPD6782	Phase 4
0.6222	Remote Similarity	NPD6777	Approved
0.6196	Remote Similarity	NPD6779	Approved
0.6196	Remote Similarity	NPD6780	Approved
0.57	Remote Similarity	NPD6776	Approved
0.5472	Remote Similarity	NPD7801	Approved
0.5278	Remote Similarity	NPD7701	Phase 2
0.5273	Remote Similarity	NPD7874	Phase 4
0.5273	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.5192	Remote Similarity	NPD7871	Phase 2
0.5143	Remote Similarity	NPD7696	Phase 3
0.5143	Remote Similarity	NPD7697	Phase 3
0.5143	Remote Similarity	NPD7698	Approved
0.5143	Remote Similarity	NPD7870	Phase 2
0.505	Remote Similarity	NPD6823	Phase 2

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